Supporting Information
|
|
- Cameron Adams
- 5 years ago
- Views:
Transcription
1 ne-pot synthesis of pyrrolidino- and piperidinoquinolinones by three-component aza-diels Alder reactions of -arylimines with in situ generated cyclic enamides. Wenxue Zhang, Yisi Dai, Xuerui Wang, Wei Zhang * State Key Laboratory of Applied rganic Chemistry and Department of Chemistry, Lanzhou University, Lanzhou, Gansu, , People s Republic of China zhangwei6275@lzu.edu.cn Supporting Information Content General Experimental procedures References Analytical data for compounds 5a-5o Analytical data for compounds 6a-6f 1 and 13 C spectra page S2 S2-S3 S3 S2-S9 S10-S12 S13-S39 1
2 General remark: All reagents were purchased from commercial suppliers and used without further purification. Flash chromatography was carried out with silica gel ( mesh). Analytical TLC was performed with silica gel GF254 plates, and the products were visualized by UV detection. 1 MR and 13 C MR (400 Mz and 100Mz, respectively) spectra were recorded in CDCl 3. Chemical shifts (δ) are reported in ppm using TMS as internal standard and spin-spin coupling contants (J) are given in z. The high resolution mass spectra (RMS) were measured on a Bruker Daltonics APEXⅡ47e spectrometer by ESI. Mp data were measured with micro melting point apparatus. The X-ray crystallographic analysis was performed with a Siemens SMART CCD and a Siemens P4 diffractometer Experimental procedures: General procedure for the preparation of 5-hydropyrrolidin-2-ones 3a, 3b, 3c: A 50 ml round-bottom flask was charged with -benzylmaleimide (346 mg, 2 mmol), CeCl (746 mg, 2 mmol), anydrous Me (10 ml), and a stirbar. The flask was cooled to 0, after 5 mintues, ab 4 (76 mg, 2 mmol) was added portionwise over 5-10 min, icl (474 mg, 2 mmol) added immediately 1, additional ab 4 (76 mg, 2 mmol) were added, the mixture was stirred for 5 minutes at 0, 10 ml water poured into the flask, and the mixture extracted with ethyl acetate (3x30 ml). The combined organic layers were dried with anhydrous a 2 S 4, filtered, and concentrated in vacuo. The residue was isolated by silica gel column chromatography to give a white solid 300 mg (85%). 3b: yield 75%, 3c: yield 20%. The preparation of 6-hydroxypiperidin-2-ones 4a 2 : A 100 ml round-bottom flask was charged with - benzyl -glutarimide (200 mg, mmol), anhydrous Me (41.3 ml), and a stirbar. The flask was cooled to 0 C. ab 4 (942 mg, 24.8 mmol) was added portionwise over 5 10 min. The reaction was stirred vigorously for 2 h at 0 C. Conversion was measured by TLC (hexane-actone 4:1). If all starting material was not consumed after 2 h, 10 additional equiv ab 4 were added every 30 minutes, until full conversion was realized. Upon complete conversion of the imide, the reaction mixture was poured onto virgorously stirring 200 ml 1:1 C 2 Cl 2 /ac 3 (sat. aq.) which had been pre-cooled to 0 C. The biphasic slurry was stirred at 0 C for 5 minutes, and the layers partitioned in a separatory funnel. The aqueous layer was extracted with C 2 Cl 2 (2 25 ml). The combined organic layers were dried over a 2 S 4, filtered, and concentrated in vacuo. The residue was isolated by silica gel column chromatography to get the product as a white solid 200 mg (85%). 2
3 General procedure for the Pyrrolidino- and Piperidinoquinolinones. sythesis of compounds 5a-5o, 6a-6f. Aromatic aldehyde (1.1 mmol ) and anilines (1.0 mmol ) were dissolved in anhydrous C 2 Cl 2 (20 ml), and 0.5 g 4 Å molecule sieves was added. The mixture was stirred at room temperature for 2 hrs, The (1.0 mmol 5-hydropyrrolidin-2-ones or 6-hydroxypiperidin-2-ones and 0.8 mmol BF 3 Et 2 were added, respectively. The mixture was stirres for another 2 h, 10 ml water was added, and the resulting mixture was extracted with C 2 Cl 2 (3 30). The organic phase was dried over a 2 S 4, filtered and the solvent was removed in vacuo. The residue was purified by flash chromatography (hexane-acetone) to give the desired products. References: (1) D. Dhawan, S. K. Grover, Synth. Commun., 1992, 22, (2) Izzat T. Raheem, Parvinder S. Thiara, and Eric. Jacobsen J. Am. Chem. Soc., 2007, 129,
4 Analytical data for compounds 5a-5o, 6a-6f: exo-5a 2 Yellow solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 8.28 (d, J = 8.8z, 2), 7.66 (d, J = 8.8z, 2), 7.43 (t, J = 8.0z, 2), 7.35 (d, J = 7.6z, 2), 7.29 (d, J = 7.2z, 1), (m, 1), 6.72 (d, J = 8.0z, 1), (m, 1), 5.66 (d, J = 8.0z, 1), 4.75 (d, J = 2.4z, 1), 3.96 (s, 1), (m, 1), 3.08 (dd, J = 11.6, 16z, 1), 2.02 (dd, J = 8.0, 16.0z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 172.4, 147.8, 147.8, 144.3, 138.3, 129.3, 128.9, 127.4, 126.4, 125.6, 124.2, 120.9, 119.6, 116.3, 59.9, 57.5, 40.6, 30.5 ppm. ESI-RMS: m/z Calcd for C : , found endo-5a 2 Yellow solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 8.24 (d, J = 8.4z, 2), 7.64 (d, J = 8.4z, 2), 7.36 (t, J = 6.8z, 3), 7.07 (d, J = 7.2z, 3), 6.64 (d, J = 8.0z, 1), (m, 2), 5.04 (d, J = 5.6z, 1), 4.38 (d, J = 9.2z, 1), 4.31 (s, 1), (m, 1), 2.72 (dd, J = 7.6, 16.8z, 1), 2.34 (dd, J = 2.4, 16.8z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 173.2, 148.5, 147.9, 137.0, 131.8, 129.5, 129.2, 128.9, 128.2, 127.7, 124.0, 117.9, 116.5, 114.9, 50.5, 56.2, 38.7, 34.9 ppm. ESI-RMS: m/z Calcd for C : , found exo-5b C 3 2 Yellow solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 8.25 (d, J = 8.8z, 2), 7.65 (d, J = 8.8z,2), (m, 3), 7.09 (dd, J = 1.6, 3.6z, 2), 6.89 (dd, J = 1.6, 8.0z, 1), 4
5 6.57 (d, J = 8.00z, 1), 6.16 (d, J = 1.2z, 1), 4.99 (d, J = 5.6z, 1), 4.36 (d, J = 9.2z, 1), 4.17 (s, 1), (m, 1), 2.48 (dd, J = 7.2, 16.8z, 1), 2.35 (dd, J = 2.4, 17.2z, 1), 1.95 (s, 3) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 173.3, 148.7, 147.9, 141.8, 137.1, 132.2, 130.1, 129.1, 129.0, 128.3, 127.7, 127.1, 124.0, 116.6, 114.8, 59.6, 56.4, 38.8, 34.9, 20.2 ppm. ESI-RMS: m/z Calcd for C : , found exo-5c Cl 2 Yellow solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 8.27 (d, J = 8.4z, 2), 7.64 (d, J = 8.8z, 2), (m, 3), 7.08 (d, J = 1.2z, 2), 7.04 (m, 1), 6.59 (d, J = 8.4z, 1), 6.34 (d, J = 2.4z, 1), 4.98 (d, J = 5.6z, 1), 4.37 (d, J = 9.2z, 1), 4,28 (s, 1), (m, 1), 2.74 (dd, J = 7.6, 16.8z, 1), 2.35 (dd, J = 2.0, 16.8z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 173.0, 148.1, 147.9, 142.7, 136.6, 131.4, 129.5, 129.4, 128.9, 128.2, 128.1, 124.1, 122.5, 117.9, 116.1, 59.1, 56.2, 38.5, 34.7 ppm. ESI-RMS: m/z Calcd for C Cl+ + : , found exo-5d C White solid, mp 234 ; 1 MR (400 Mz, CDCl 3 ) δ: 7.70 (d, J = 8.4z, 2), 7.58 (d, J = 8.4z, 2), (m, 3), (m, 3), 6.64 (d, J = 7.6z, 1), (m, 2), 5.03 (d, J = 5.2z, 1), 4.33 (d, J = 14.8z, 1), 4.25 (s, 1), (m, 1), 2.72 (dd, J = 7.2, 16.4z, 1), 2.33 (dd, J = 2.0, 16.4z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 173.3, 146.5, 144.3, 137.0, 132.7, 131.9, 129.4, 129.2, 128.9, 128.2, 127.8, 117.9, 116.5, 114.8, 112.4, 59.6, 56.4, 38.7, 34.9 ppm. ESI-RMS: m/z Calcd for C : , found endo-5d C 5
6 White solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 7.72 (d, J = 8.0z, 2), 7.59 (d, J = 8.0z, 2), 7.43 (t, J = 7.6z, 2), 7.32 (dd, J = 7.6, 24.4z, 1), (m, 1), 6.71 (d, J = 7.6z, 1), (m, 2), 5.64 (d, J = 8.0z, 1), 4.69 (s, 1), 3.92 (s, 1), 3.22 (dd, J = 8.4z, 1), 3.08 (dd, J = 11.6, 16z, 1), 2.03 (dd, J = 7.6, 16z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 172.4, 145.8, 144.3, 138.2, 132.7, 129.3, 128.8, 127.3, 126.4, 125.6, 120.8, 119.5, 118.3, 116.2, 112.2, 60.0, 57.7, 40.7, 30.6 ppm. ESI-RMS: m/z Calcd for C : , found exo-5e C 3 C White solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 7.68 (d, J = 8.0z, 2), 7.58 (d, J = 8.4z, 2), (m, 3), 7.05 (d, J = 7.2z, 1), 6.88 (d, J = 8.0z, 1), 6.55 (d, J = 8.4z, 1), 6.15 (s, 1), 4.98 (d, J = 5.6z, 1), 4.28 (d, J = 9.2z, 1), 4.14 (s, 1), (m, 1), 2.71 (dd, J = 7.2, 16.4z, 1), 2.33 (dd, J = 2.0, 16.8z, 1), 1.94 (s, 3) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 173.4, 146.7, 141.9, 137.0, 132.6, 132.2, 130.1, 129.0, 128.8, 128.3, 127.7, 127.0, 118.3, 116.5, 114.7, 112.3, 59.7, 56.6, 38.7, 34.9, 21.0 ppm. ESI-RMS: m/z Calcd for C : , found exo-5f Cl C White solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 7.58 (d, J = 8.0z, 2), 7.46 (t, J = 8.0z, 2), 7.23 (d, J = 8.4z, 2), 7.04 (dd, J = 2.0, 8.4z, 1), 6.65 (d, J = 8.4z, 1), 6.49 (d, J = 1.2z, 1), 5.55 (d, J = 8.0z, 1), 4.66 (d, J = 2.8z, 1), 4.00 (s, 1), (m, 1), 3.03 (dd, J = 12.0, 16.4z, 1), 2.03 (dd, J = 8.4, 16.4z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 172.2, 145.4, 142.9, 137.7, 132.8, 129.5, 129.0, 128.8, 127.2, 126.9, 125.6, 124.0, 122.1, 118.2, 117.4, 112.3, 59.7, 57.6, 40.3, 30.3 ppm. ESI-RMS: m/z Calcd for C Cl+ + : , found exo-5g 6
7 White solid, mp 227 ; 1 MR (400 Mz, CDCl 3 ) δ: (m, 9), (m, 1), 7.06 (dt, J =1.6, 8.4z, 1),6.68 (d, J = 7.6z, 1), 6.58 (d, J =7.2z, 1),6.50 (dt, J = 0.8, 2.8z, 1), 5.64 (d, J = 7.6z, 1),4.62 (d, J = 2.4z, 1), 3.93(s, 1), (m, 2), 2.10 (dd, J =6.8, 15.6z, 1), ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 173.1, 145.2, 140.5, 138.4, 129.2, 129.2, 128.8, 128.6, 125.1, 126.4, 126.2, 125.6, 120.9, 118.8, 115.6, 60.2, 57.9, 41.1, 30.8 ppm. ESI-RMS: m/z Calcd for C : , found exo-5h 2 Yellow solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 8.24 (d, J = 8.8z, 2), 7.57 (d, J = 8.4z, 2), 7.39 (t, J = 7.2z, 2), (m, 3), (m, 2), (m, 1), 6.77 (d, J = 8.0z, 1), 5.26 (d, J = 15.6z, 1), 4.76 (d, J = 8.8z, 1), 4.52 (d, J = 2.8z, 1), 3.95 (d, J = 15.6z, 1), 3.89 (s, 1), (m, 1), 2.98 (dd, J = 10.4, 16.0z, 1), 1.96 (dd, J = 8.4, 16.0z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 173.4, 147.7, 147.6, 146.1, 136.0, 130.1, 138.9, 128.7, 127.8, 127.6, 127.3, 124.0, 121.4, 119.8, 116.7, 58.7, 55.8, 44.0, 40.7, 29.4 ppm. ESI-RMS: m/z Calcd for C : , found exo-5i C 3 2 Yellow solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 8.23 (d, J = 8.8z, 2), 7.56 (d, J = 8.8z, 2), 7.39 (t, J = 6.8z, 2), 7.27 (d, J = 12.0z, 2), 6.97 (s, 1), 6.96 (d, J = 8.0z, 1), 6.67 (d, J = 8.0z, 1), 5.21 (d, J = 15.6z, 1), 4.73 (d, J = 8.4z, 1), 4,48 (d, J = 2.8z, 1), 3.99 (d, J = 15.6z, 1), 3.79 (s, 1), (m, 1), 2.97 (dd, J = 10.4, 16.0z, 1), 2,27 (s, 3), 1.94 (dd, J = 8.4, 16.0z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 173.5, 147.9, 147.6, 143.6, 136.2, 130.5, 129.4, 129.0, 128.8, 127.8, 127.5, 127.3, 124.0, 121.2, 116.8, 58.9, 56.1, 44.2, 40.7, 29.4, 20.7 ppm. ESI-RMS: m/z Calcd for C : 7
8 , found exo-5j Cl 2 Yellow solid, mp 243 ; 1 MR (400 Mz, CDCl 3 ) δ: 8.25 (d, J = 8.8z, 2), 7.56 (d, J = 8.2z, 2), 7.41 (t, J = 7.6z, 2), 7.28 (d, J = 7.2z, 3), 7.15 (d, J = 2.4z, 1), 7.11 (dd, J = 2.4, 8.8z, 1), 6.70 (d, J = 8.4z, 1), 5.26 (d, J = 16.0z, 1), 4,71 (d, J = 8.8z, 1), 4,50 (d, J = 2.8z, 1), 3.94 (d, J = 15.2z, 1), 3.93 (s, 1), (m, 1), 2.93 (dd, J = 10.4, 16.4z, 1), 1.97 (dd, J = 8.8, 16.4z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 173.3, 147.7, 147.2, 144.6, 135.7, 129.8, 129.0, 128.7, 127.8, 127.3, 124.4, 124.1, 122.7, 117.9, 58.6, 55.6, 44.2, 40.4, 29.3 ppm. ESI-RMS: m/z Calcd for C Cl+ + : , found exo-5k C White solid, mp 240 ; 1 MR (400 Mz, CDCl 3 ) δ: 7.66 (d, J = 8.4z, 2), 7.49 (d, J = 8.4z, 2), 7.38 (t, J = 7.2z, 2), 7.27 (t, J = 6.8z, 3), (m, 2), 6.84 (t, J = 6.8z, 1), 6,75 (d, J = 7.6z, 1), 4.74 (d, J = 8.4z, 1), 4.45 (d, J = 2.8z, 1), 3.93 (d, J = 15.6z, 1), 3.91 (s, 1), 3.04 (m, 1), 2.95 (dd, J = 10.4, 16.0z, 1), 1.93 (dd, J = 8.4, 16.0z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 173.4, 146.2, 145.7, 136.0, 132.6, 130.0, 128.8, 128.7, 127.8, 127.6, 127.2, 121.3, 119.7, 118.4, 116.7, 111.9, 58.8, 55.8, 43.9, 40.7, 29.4 ppm. ESI-RMS: m/z Calcd for C : , found exo-5l C 3 C White solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 7.65 (d, J = 8.0z, 2), 7.49 (d, J = 8.0z, 2), 7.38 (t, J = 7.2z, 2), 7.26 (d, J = 8.4z, 3), 6.94 (d, J = 8.0z, 1), 6.95 (s, 1), 6.80 (d, J = 7.6z, 1), 5.20 (d, J = 15.6z, 1), 4.71 (d, J = 4,4z, 1), 4.41 (d, J = 2.4z, 1), 3.97 (d, J = 15.6z, 1), 3.79 (s, 1), (m, 1), 2.94 (dd, J = 10.4, 8
9 16.0z, 1), 2.26 (s, 3), 1.91 (dd, J = 8.0, 16.0z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 178.6, 145.9, 143.7, 136.1, 132.5, 130.5, 129.3, 128.9, 128.8, 127.7, 127.5, 127.2, 121.1, 118.3, 116.6, 111.8, 59.0, 56.1, 44.1, 43.7, 40.6, 29.3, 20.6 ppm. ESI-RMS: m/z Calcd for C : , found exo-5m C 3 C 3 White solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 7.39 (d, J = 6.8z, 2), , (m, 5), 6.91 (t, J = 8.8z, 4), 6.61 (d, J = 8.0z, 1), 5.22 (d, J = 16.0z, 1), 4.68 (d, J = 8.8z, 1), 4.30 (d, J = 2.0z, 1), 3.98 (d, J = 15.6z, 1), 3.81 (s, 3), 3.70 (s, 1), (m, 2), 2.26 (s, 3), (m, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ:174.4, 159.2, 144.8, 136.4, 132.6, 130.5, 129.1, 128.8, 128.2, 127.8, 127.5, 127.4, 121.3, 116.3, 114.1, 58.8, 56.4, 55.3, 44.1, 41.2, 29.6, 20.6 ppm. ESI-RMS: m/z Calcd for C : , found exo-5n White solid, mp 238 ; 1 MR (400 Mz, CDCl 3 ): δ: (m, 6), (m, 4), (M, 2),6.82 (t, J = 7.2z, 1), 6.72 (d, J =8.0z, 1),5.28 (d, J = 15.6, 1),4.73 (d, J = 8.0z, 1),4.41 (d, J = 2.0z, 1), 3.94(d, J = 15.6, 1), 3.84 (s, 1), 3.07 (dd, J = 10.4, 20.4z, 2), 2.03 (dd, J =13.2, 20.8z, 1), ppm. 13 C MR (100 Mz, CDCl 3 ) δ:174.1, 147.1, 140.4, 131.2, 130.1, 128.8, 128.8, 128.5, 127.9, 127.8, 127.5, 126.4, 121.5, 119.1, 116.4, 59.1, 56.0, 43.8, 41.0, 29.4 ppm. ESI-RMS: m/z Calcd for C : , found exo-5o C 3 C MR (400 Mz, CDCl 3 ) δ: 8.23 (d, J = 8.8z, 2), 7.61 (d, J = 8.8z, 2), 7.05 (s, 1), 9
10 7.02 (d, J = 8.4z, 1), 6.61 (d, J = 8.0z, 1), 4.52 (d, J = 5.2z, 1), 4.13 (s, 1), 4.07 (d, J = 10.4z, 1), 2.87 (s, 3), (m, 1), 2.46 (dd, J = 7.2, 8.4z, 1), 2.31 (s, 3), 2.04 (d, J = 16.8z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 173.0, 148.4, 148.0, 142.5, 132.1, 130.5, 129.2, 127.4, 123.9, 115.4, 115.3, 58.3, 56.4, 37.9, 34.3, 27.6, 20.4 ppm. ESI-RMS: m/z Calcd for C : , found endo-5o C 3 C MR (400 Mz, CDCl 3 ) δ: 8.25 (t, J = 4.4z, 2), 7.58 (d, J = 8.8z, 2), 7.08 (s, 1), 6.98 (d, J = 8.4z, 1), 6.68 (d, J = 8.0z, 1), 4.79 (d, J = 8.8z, 1), 4.56 (d, J = 2.8z, 1), 3.78 (s, 1), (m, 1), 2.95 (s, 1), (m, 1), 2,29 (s, 1), 1.83 (dd, J = 9.2, 16.8z, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 173.1, 147.9, 147.6, 143.4, 130.1, 129.5, 129.1, 127.3, 124.0, 121.0, 116.7, 60.3, 58.7, 40.6, 29.3, 29.2, 20.7 ppm. ESI-RMS: m/z Calcd for C : , found endo-6a 2 Yellow solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 8.22 (d, J = 8.8z, 2), 7.53 (d, J = 8.4z, 2), (m, 5), (m, 2), 6.80 (t, J = 7.2z, 2), 6.65 (dd, J = 1.2, 8.0z, 1), 5,88 (d, J = 14.8z, 1), 4.91 (d, J = 3.2z, 1), 4.85 (d, J = 4.0z, 1), 4.08 (d, J = 14.8z, 1), 4.05 (s, 1), (m, 2), (m, 1), (m, 1), (m, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 170.8, 148.3, 147.6, 142.7, 137.3, 128.8, 128.7, 128.0, 127.7, 127.4, 126.2, 123.8, 120.4, 119.0, 114.5, 58.2, 57.5, 51.6, 38.4, 29.9, 16.9 ppm. ESI-RMS: m/z Calcd for C : , found exo-6a 2 10
11 Yellow solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 8.05 (d, J = 8.8z, 2), 7.28 (d, J = 8.8z, 2), 7.26 (s, 1), (m, 4), (m, 2), 6.75 (t, J = 7.2z, 1), 6.63 (d, J = 8.0z, 1), 5.52 (d, J = 14.4z, 1), 4.35 (s, 1), 4.07 (d, J = 3.6z, 1), 3.41 (d, J = 14.4z, 1), (m, 1), (m, 1), (m, 1), (m, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 170.6, 151.4, 147.2, 142.2, 136.8, 128.9, 128.3, 128.0, 127.2, 127.1, 126.7, 123.7, 118.8, 117.9, 113.4, 57.3, 52.0, 49.9, 38.4, 29.8, 22.4 ppm. ESI-RMS: m/z Calcd for C : , found endo-6b 3 C 2 Yellow solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 8.21 (d, J = 8.8z, 2), 7.52 (d, J = 8.4z, 2), (m, 5), 6.94 (d, J = 8.0z, 1), 6.90 (s, 1), 6.56 (d, J = 8.0z, 1), 5.83 (d, J = 14.4z, 1), (m, 2), 4.13 (d, J = 14.8z, 1), 3.96 (s, 1), (m, 2), 2.31 (s, 3), (m, 1), (m, 1), (m, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 171.0, 148.5, 147.5, 140.3, 137.4, 129.2, 128.7, 128.4, 128.0, 127.7, 127.4, 126.5, 123.8, 120.4, 114.7, 58.2, 57.7, 51.8, 38.6, 29.9, 20.6, 16.9 ppm. ESI-RMS: m/z Calcd for C : , found exo-6b 3 C 2 Yellow solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 8.03 (d, J = 8.8z, 2), 7.28 (d, J = 8.2z, 2), (m, 3), 6.97 (m, 3), 6.82 (s, 1), 6.55 (d, J = 8.0z, 1), 5.58 (d, J = 14.4z, 1), 4.34 (t, J = 3.2z, 1), 4.25 (t, J = 3.2z, 1), 4.03 (d, J = 14.4z, 1), 3.92 (d, J = 14.4z, 1), (m, 2), 2.24 (s, 3), (m, 1), (m, 1), (m, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 170.7, 151.7, 147.1, 139.8, 136.9, 129.5, 128.2, 128.0, 127.3, 127.2, 127.2, 126.7, 123.7, 118.9, 113.5, 57.5, 52.0, 50.0, 38.6, 29.8, 22.5, 20.5 ppm. ESI-RMS: m/z Calcd for C : , found endo-6c 11
12 C White solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 7.65 (d, J = 8.4z, 2), 7.46 (d, J = 8.4z, 2), (m, 5), (m, 2), 7.78 (t, J = 8.0z, 1), 6.79 (dd, J = 0.8, 8.4z, 1), 5.87 (d, J = 14.8z, 1), 4.86 (d, J = 14.8z, 1), (m, 1), 4.05 (s, 1), 2.32 (t, J = 6.4z, 2), (m, 1), (m, 1), (m, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 170.8, 146.3, 142.7, 137.2, 132.4, 128.7, 128.6, 128.0, 127.6, 127.3, 126.1, 120.3, 118.8, 118.4, 114.5, 111.8, 58.3, 57.6, 51.6, 38.3, 29.9, 16.9 ppm. ESI-RMS: m/z Calcd for C : , found exo-6c C White solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 7.50 (d, J = 8.4z, 2), 7.24 (d, J = 8.0z, 2), (m, 4), 7.05 (m, J = 8.0z, 1), 6.97 (d, J = 6.8z, 2), 6.76 (m, 1), 6.61 (d, J = 8.0z, 1), 5.54 (d, J = 14.4z, 1), 4.27 (t, J = 8.8z, 1), 4.28 (s, 1), 4.07 (d, J = 4.0z, 1), 3.95 (d, J = 14.8z, 1), (m, 2), (m, 1), (m, 1), (m, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 170.8, 149.4, 142.3, 136.7, 132.2, 128.9, 128.3, 127.9, 127.3, 127.0, 126.6, 118.7, 118.5, 117.7, 113.4, 111.1, 57.4, 52.1, 49.8, 38.3, 29.7, 22.4 ppm. ESI-RMS: m/z Calcd for C : , found endo-6d 3 C C White solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 7.64 (d, J = 8.4z, 2 ) 7.46 (d, J = 8.4z, 2), (m, 5), 6.93 (d, J = 8.0z, 1), 6.89 (s, 1), 6.54 (d, J = 8.4z, 1), 5,82 (d, J = 14.4z, 1), 4.81 (t, J = 5.6z, 1), 4.12 (d, J = 14.8z, 1), 3.90 (s, 1), 2.31 (t, J = 5.6z, 2), 2.24 (s, 3), (m, 1), (m, 1), (m, 1) ppm. 13 C 12
13 MR (100 Mz, CDCl 3 ) δ: 171.1, 146.5, 140.3, 137.3, 132.3, 129.2, 128.7, 128.0, 127.7, 127.6, 127.3, 126.5, 120.4, 114.6, 111.7, 58.4, 57.7, 51.8, 35.5, 29.9, 20.6, 16.8 ppm. ESI-RMS: m/z Calcd for C : , found exo-6d 3 C C White solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: 7.36 (d, J = 6.8z, 2), 7.23 (d, J = 8.4z, 2), (m, 3), (m, 3), 6.82 (s, 1), 6.53 (d, J = 8.0z, 1), 5.57 (d, J = 14.8z, 1), 4.27 (s, 1), 4.16 (s, 1), 4.04 (d, J = 8.0z, 1), 3.93 (d, J = 14.4z, 1), (m, 2), 2.24 (s, 3), (m, 1), (m, 1), (m, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 170.8, 149.7, 139.9, 136.9, 132.3, 129.5, 128.3, 128.0, 127.4, 127.3, 127.1, 126.6, 118.9, 118.5, 113.5, 111.2, 57.6, 52.2, 50.0, 38.5, 29.9, 22.5, 20.5 ppm ESI-RMS: m/z Calcd for C : , found endo-6e White solid, mp 228 ; 1 MR (400 Mz, CDCl 3 ) δ: (m, 3), (m, 6), 6.98 (d, J = 6.4z, 3), 6.68 (t, J = 7.6z, 1), 6.55 (d, J = 8.0z, 1), 5.35 (d, J = 14.8z, 1), 4.34 (d, J = 3.2z, 1), 4.25 (s, 1), 4.22 (d, J = 5.2z, 1), 4.06(d, J = 14.8z, 1),, (m, 2), (m, 1), (m, 1), (m, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 171.1, 143.4, 143.3, 137.3, 128.9, 128.5, 128.2, 128.1, 127.7, 127.5, 126.9, 126.2, 118.4, 116.9, 113.3, 57.3, 53.8, 49.2, 38.4, 29.9, 22.7 ppm. ESI-RMS: m/z Calcd for C : , found exo-6e 13
14 White solid, mp 235 ; 1 MR (400 Mz, CDCl 3 ) δ: (m, 10), 7.10 (t, J = 8.0z, 2), 6.73 (t, J = 7.2z, 1), 6.59 (d, J = 7.6z, 1), 5.86 (d, J = 12.8z, 1), 4.82 (d, J = 4.0z, 1), 4.79 (d, J = 2.8z, 1), 4.07 (d, J = 12.8z, 1), 4.07 (s, 1), (m, 2), (m, 1), (m, 1), (m, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 171.2, 143.4, 140.7, 137.3, 128.7, 128.5, 128.4, 127.8, 127.8, 127.5, 126.5, 126.1, 120.1, 117.9, 113.9, 58.4, 57.8, 51.6, 38.3, 30.07, 16.9 ppm ESI-RMS: m/z Calcd for C : , found endo-6f 3 C C 3 White solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: , (m, 3), 7.09 (d, J = 8.8z, 2), (m, 2), 6.92 (d, J = 9.6z, 1), 6.78 (d, J = 8.8z, 2), 6.72 (s, 1), 6.46 (d, J = 8.0z, 1), 5.37 (d, J = 14.8z 1), 4.32 (d, J = 4.0z, 1), 4.14 (d, J = 6.0z, 1), 4.06 (d, J = 14.4z, 1),.4.05 (s,1), 3.78 (s, 3), (m, 2), 2.20 (s, 3), 2.17(s, 1), (m, 1), (m,1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 171.2, , 141.1, 137.6, 135.7, 129.5, 128.6, 128.2, 127.8, 127.3, 126.9, 126.1, 118.5, 113.9, 113.4, 57.0, 55.2, 54.1, 49.2, 38.8, 30.0, 22.5, 20.4 ppm. ESI-RMS: m/z Calcd for C : , found exo-6f 3 C C 3 White solid, mp ; 1 MR (400 Mz, CDCl 3 ) δ: , (m, 4), (m, 3), (m, 4), 6.49 (d, J = 8.0z, 1), 5.82 (d, J = 14.4z, 1), 4.80 (d, J = 4.4z, 1), 4.70 (d, J = 2.8z, 1), 4.12 (d, J = 14.4z, 1), 3.86 (s, 1), 3.80 (s, 3), (dt, J = 4.4, 7.6z 2), 2.14 (s, 3), (m, 1), (m, 1), (m, 1) ppm. 13 C MR (100 Mz, CDCl 3 ) δ: 171.4, 159.2, 141.1, 137.5, 132.9, 129.0, 128.7, 128.0, 127.6, 127.5, 127.2, 126.6, 120.3,114.1, 113.4, 58.0, 58.0, 55.3, 51.8, 38.8, 30.2, 20.6, 17.0 ppm. ESI-RMS: m/z Calcd for C : , found
15 1 MR and 13 C MR Spectra endo-5a 15
16 exo-5a 16
17 exo-5b 17
18 exo-5c 18
19 endo-5d 19
20 exo-5d 20
21 exo-5e 21
22 exo-5f 22
23 exo-5g 23
24 exo-5h 24
25 exo-5i 25
26 exo-5j 26
27 exo-5k 27
28 exo-5l 28
29 exo-5m 29
30 exo-5n 30
31 endo-5o 31
32 exo-5o 32
33 endo-6a 33
34 exo-6a 34
35 endo-6b 35
36 exo-6b 36
37 endo-6c 37
38 exo-6c 38
39 endo-6d 39
40 exo-6d 40
41 endo-6e 41
42 exo-6e 42
43 endo-6f 43
44 exo-6f 44
Indium Triflate-Assisted Nucleophilic Aromatic Substitution Reactions of. Nitrosobezene-Derived Cycloadducts with Alcohols
Supporting Information Indium Triflate-Assisted ucleophilic Aromatic Substitution Reactions of itrosobezene-derived Cycloadducts with Alcohols Baiyuan Yang and Marvin J. Miller* Department of Chemistry
More informationCurtius-Like Rearrangement of Iron-Nitrenoid Complex and. Application in Biomimetic Synthesis of Bisindolylmethanes
Supporting Information Curtius-Like Rearrangement of Iron-itrenoid Complex and Application in Biomimetic Synthesis of Bisindolylmethanes Dashan Li,, Ting Wu,, Kangjiang Liang,, and Chengfeng Xia*,, State
More informationSupporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supporting Information TEMPO-catalyzed Synthesis of 5-Substituted Isoxazoles from Propargylic
More informationN-Hydroxyphthalimide: a new photoredox catalyst for [4+1] radical cyclization of N-methylanilines with isocyanides
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2016 Electronic supplementary information for -Hydroxyphthalimide: a new photoredox catalyst for [4+1]
More informationElectronic Supplementary Material
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Material A Novel Functionalized Pillar[5]arene: Synthesis, Assembly
More informationHalogen halogen interactions in diiodo-xylenes
Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information (ESI) for CrystEngComm. This journal is The Royal Society
More informationSynthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes
Supporting Information to Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed Cascade Trifluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes Yan Zhang*, Dongmei Guo, Shangyi
More informationTetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon
SUPPLEMENTARY METHODS Solvents, reagents and synthetic procedures All reactions were carried out under an argon atmosphere unless otherwise specified. Tetrahydrofuran (THF) was distilled from benzophenone
More informationDiastereoselectivity in the Staudinger reaction of. pentafluorosulfanylaldimines and ketimines
Supporting Information for Diastereoselectivity in the Staudinger reaction of pentafluorosulfanylaldimines and ketimines Alexander Penger, Cortney. von ahmann, Alexander S. Filatov and John T. Welch* Address:
More informationElectronic Supplementary Information (12 pages)
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 A C 2 -responsive pillar[5]arene: synthesis and self-assembly in water Kecheng Jie, Yong Yao, Xiaodong
More informationSupporting Information
Supporting Information Total Synthesis of (±)-Grandilodine B Chunyu Wang, Zhonglei Wang, Xiaoni Xie, Xiaotong Yao, Guang Li, and Liansuo Zu* School of Pharmaceutical Sciences, Tsinghua University, Beijing,
More informationAn Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol
An Efficient Total Synthesis and Absolute Configuration Determination of Varitriol Ryan T. Clemens and Michael P. Jennings * Department of Chemistry, University of Alabama, 500 Campus Dr. Tuscaloosa, AL
More informationPalladium-Catalyzed Oxidative Cyclization of Tertiary Enamines for Synthesis of 1,3,4-Trisubstituted Pyrroles and 1,3-Disubstituted Indoles
Supporting Information for Palladium-Catalyzed Oxidative Cyclization of Tertiary Enamines for Synthesis of 1,3,4-Trisubstituted Pyrroles and 1,3-Disubstituted Indoles Xiao-Li Lian, Zhi-Hui Ren, Yao-Yu
More informationSupporting Information
Supporting Information Wiley-VCH 2006 69451 Weinheim, Germany A Highly Enantioselective Brønsted Acid Catalyst for the Strecker Reaction Magnus Rueping, * Erli Sugiono and Cengiz Azap General: Unless otherwise
More informationThe First Asymmetric Total Syntheses and. Determination of Absolute Configurations of. Xestodecalactones B and C
Supporting Information The First Asymmetric Total Syntheses and Determination of Absolute Configurations of Xestodecalactones B and C Qiren Liang, Jiyong Zhang, Weiguo Quan, Yongquan Sun, Xuegong She*,,
More informationHow to build and race a fast nanocar Synthesis Information
How to build and race a fast nanocar Synthesis Information Grant Simpson, Victor Garcia-Lopez, Phillip Petemeier, Leonhard Grill*, and James M. Tour*, Department of Physical Chemistry, University of Graz,
More informationPhil S. Baran*, Jeremy M. Richter and David W. Lin SUPPORTING INFORMATION
Direct Coupling of Pyrroles with Carbonyl Compounds: Short, Enantioselective Synthesis of (S)-Ketorolac Phil S. Baran*, Jeremy M. Richter and David W. Lin SUPPRTIG IFRMATI General Procedures. All reactions
More informationSUPPORTING INFORMATION
Dynamic covalent templated-synthesis of [c2]daisy chains. Altan Bozdemir, a Gokhan Barin, a Matthew E. Belowich, a Ashish. Basuray, a Florian Beuerle, a and J. Fraser Stoddart* ab a b Department of Chemistry,
More informationSupporting Information
Supporting Information Synthesis of H-Indazoles from Imidates and Nitrosobenzenes via Synergistic Rhodium/Copper Catalysis Qiang Wang and Xingwei Li* Dalian Institute of Chemical Physics, Chinese Academy
More informationSupporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Pd-Catalyzed C-H Activation/xidative Cyclization of Acetanilide with orbornene:
More informationPTSA-Catalyzed Green Synthesis of 1,3,5-Triarylbenzene under Solvent-Free Conditions
S1 Supporting Information PTSA-Catalyzed Green Synthesis of 1,3,5-Triarylbenzene under Solvent-Free Conditions Yanan Zhao, a Jian Li, a Chunju Li, a Kun Yin, a Dongyan Ye a and Xueshun Jia*, a, b a Department
More informationSynthesis of fluorophosphonylated acyclic nucleotide analogues via Copper (I)- catalyzed Huisgen 1-3 dipolar cycloaddition
Synthesis of fluorophosphonylated acyclic nucleotide analogues via Copper (I)- catalyzed Huisgen 1-3 dipolar cycloaddition Sonia Amel Diab, Antje Hienzch, Cyril Lebargy, Stéphante Guillarme, Emmanuel fund
More informationSupporting Information. DBU-Mediated Metal-Free Oxidative Cyanation of α-amino. Carbonyl Compounds: Using Molecular Oxygen as the Oxidant
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information DBU-Mediated Metal-Free Oxidative Cyanation of α-amino
More informationStructural Elucidation of Sumanene and Generation of its Benzylic Anions
Structural Elucidation of Sumanene and Generation of its Benzylic Anions idehiro Sakurai, Taro Daiko, iroyuki Sakane, Toru Amaya, and Toshikazu irao Department of Applied Chemistry, Graduate School of
More informationDomino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes
Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes Jian Gong, Fuchun Xie, Wenming Ren, Hong Chen and Youhong Hu* State Key Laboratory of Drug Research,
More information5.37 Introduction to Organic Synthesis Laboratory
MIT pencourseware http://ocw.mit.edu 5.37 Introduction to rganic Synthesis Laboratory Spring 2009 For information about citing these materials or our Terms of Use, visit: http://ocw.mit.edu/terms. URIECA
More informationSupporting Information
Supporting Information Efficient Short Step Synthesis of Corey s Tamiflu Intermediate Nsiama Tienabe Kipassa, Hiroaki kamura, * Kengo Kina, Tetsuo Iwagawa, and Toshiyuki Hamada Department of Chemistry
More informationSupporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Rh 2 (Ac) 4 -Catalyzed 2,3-Migration of -rrocenecarboxyl -Diazocarbonyl
More informationSupplementary Information
Supplementary Information C aryl -C alkyl bond formation from Cu(ClO 4 ) 2 -mediated oxidative cross coupling reaction between arenes and alkyllithium reagents through structurally well-defined Ar-Cu(III)
More informationSupporting Information for
Supporting Information for Room Temperature Palladium-Catalyzed Arylation of Indoles icholas R. Deprez, Dipannita Kalyani, Andrew Krause, and Melanie S. Sanford* University of Michigan Department of Chemistry,
More informationSupporting Information. Table of Contents. 1. General Notes Experimental Details 3-12
Supporting Information Table of Contents page 1. General Notes 2 2. Experimental Details 3-12 3. NMR Support for Timing of Claisen/Diels-Alder/Claisen 13 4. 1 H and 13 C NMR 14-37 General Notes All reagents
More informationSupporting Information
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2012 Subcellular Localization and Activity of Gambogic Acid Gianni Guizzunti,* [b] Ayse Batova, [a] Oraphin Chantarasriwong,
More informationSupporting Information
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information Palladium-Catalyzed Regio-selective xidative C-H
More informationSynthesis of Glaucogenin D, a Structurally Unique. Disecopregnane Steroid with Potential Antiviral Activity
Supporting Information for Synthesis of Glaucogenin D, a Structurally Unique Disecopregnane Steroid with Potential Antiviral Activity Jinghan Gui,* Hailong Tian, and Weisheng Tian* Key Laboratory of Synthetic
More informationNanocrystalline Magnesium Oxide-Stabilized Palladium(0): An Efficient and Reusable Catalyst for the Synthesis of N-(2- pyridyl)indoles
Electronic Supplementary Material (ESI) for ew Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre ational de la Recherche Scientifique 2015 Supplementary Material (ESI)
More informationSilver-catalyzed decarboxylative acylfluorination of styrenes in aqueous media
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Silver-catalyzed decarboxylative acylfluorination of styrenes in aqueous
More informationSupporting Information
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2017 Supporting Information Direct copper-catalyzed oxidative trifluoromethylthiolation
More informationSupporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A
Fuerst et al. Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A S1 Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers:
More informationSupporting Information:
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2016 Supporting Information: A metal free reduction of aryl-n-nitrosamines to corresponding hydrazines
More informationSYNTHESIS OF A 3-THIOMANNOSIDE
Supporting Information SYNTHESIS OF A 3-THIOMANNOSIDE María B Comba, Alejandra G Suárez, Ariel M Sarotti, María I Mangione* and Rolando A Spanevello and Enrique D V Giordano Instituto de Química Rosario,
More informationElectronic Supplementary Information for. A Redox-Nucleophilic Dual-Reactable Probe for Highly Selective
Electronic Supplementary Information for A Redox-Nucleophilic Dual-Reactable Probe for Highly Selective and Sensitive Detection of H 2 S: Synthesis, Spectra and Bioimaging Changyu Zhang, 1 Runyu Wang,
More informationElectronic Supplementary Information
Electronic Supplementary Information Regiodivergent Heterocyclization: A Strategy for the Synthesis of Substituted Pyrroles and Furans Using α-formyl Ketene Dithioacetals as Common Precursors Ting Wu,
More informationAsymmetric Michael Addition Reactions of Nitroalkanes to 2-Furanones Catalyzed by Bifunctional Thiourea catalysts
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 25 Asymmetric Michael Addition Reactions of Nitroalkanes to 2-Furanones Catalyzed
More informationBrønsted Base-Catalyzed Reductive Cyclization of Alkynyl. α-iminoesters through Auto-Tandem Catalysis
Supporting Information Brønsted Base-Catalyzed Reductive Cyclization of Alkynyl α-iminoesters through Auto-Tandem Catalysis Azusa Kondoh, b and Masahiro Terada* a a Department of Chemistry, Graduate School
More informationSupporting Information
Supporting Information Nano CuFe 2 O 4 as a Magnetically Separable and Reusable Catalyst for the Synthesis of Diaryl / Aryl Alkyl Sulfides via Cross-Coupling Process under Ligand Free Conditions Kokkirala
More informationSynthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain
rganic Lett. (Supporting Information) 1 Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain Charles Kim, Richard Hoang and Emmanuel A. Theodorakis* Department of Chemistry
More informationSupporting information for A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline
Supporting information for A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline Chunpu Li 1,2, Lei Zhang 2, Shuangjie Shu 2 and Hong Liu* 1,2 Address: 1 Department of Medicinal
More informationDevelopment of a Reversible Fluorescent Gold Sensor with High. Selectivity
Supporting Information for Development of a Reversible Fluorescent Gold Sensor with igh Selectivity Jiaoliang Wang, Weiying Lin*, Lin Yuan, Jizeng Song, and Wensha Gao State Key Laboratory of Chemo/Biosensing
More informationRed Color CPL Emission of Chiral 1,2-DACH-based Polymers via. Chiral Transfer of the Conjugated Chain Backbone Structure
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via Chiral Transfer of the Conjugated
More informationSupporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 214 Supporting Information Rapid and sensitive detection of acrylic acid using a novel fluorescence
More informationElectronic Supplementary Information
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information Visible light-mediated dehydrogenative
More informationZn-Catalyzed Diastereo- and Enantioselective Cascade. Reaction of 3-Isothiocyanato Oxindoles and 3-Nitroindoles:
Zn-Catalyzed Diastereo- and Enantioselective Cascade Reaction of 3-Isothiocyanato xindoles and 3-itroindoles: tereocontrolled yntheses of Polycyclic pirooxindoles Jian-Qiang Zhao,, Zhi-Jun Wu, Ming-Qiang
More informationSupporting Information
Supporting Information ACA: A Family of Fluorescent Probes that Bind and Stain Amyloid Plaques in Human Tissue Willy M. Chang, a Marianna Dakanali, a Christina C. Capule, a Christina J. Sigurdson, b Jerry
More informationRational design of a ratiometric fluorescent probe with a large emission shift for the facile detection of Hg 2+
Rational design of a ratiometric fluorescent probe with a large emission shift for the facile detection of Hg 2+ Weimin Xuan, a Chen Chen, b Yanting Cao, a Wenhan He, a Wei Jiang, a Kejian Li, b* and Wei
More informationMetal-free general procedure for oxidation of secondary amines to nitrones
S1 Supporting information Metal-free general procedure for oxidation of secondary amines to nitrones Carolina Gella, Èric Ferrer, Ramon Alibés, Félix Busqué,* Pedro de March, Marta Figueredo,* and Josep
More informationSupplementary Information. Novel Stereocontrolled Amidoglycosylation of Alcohols with Acetylated Glycals and Sulfamate Ester
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supplementary Information Novel Stereocontrolled Amidoglycosylation of Alcohols with Acetylated
More informationSupporting Information for. Singlet oxygen initiated cascade transformation of a simple difuran into the key ABC motif of the pectenotoxins
Supporting Information for Singlet oxygen initiated cascade transformation of a simple difuran into the key ABC motif of the pectenotoxins Georgios Vassilikogiannakis, * Ioanna Alexopoulou, Maria Tofi
More informationph-responsive assembly and disassembly of a supramolecular cryptand-based pseudorotaxane driven by π-π stacking interaction
ph-responsive assembly and disassembly of a supramolecular cryptand-based pseudorotaxane driven by π-π stacking interaction Xuzhou Yan, Mingming Zhang, Peifa Wei, Bo Zheng, Xiaodong Chi, Xiaofan Ji, and
More informationA "turn-on" coumarin-based fluorescent sensor with high selectivity for mercury ions in aqueous media
A "turn-on" coumarin-based fluorescent sensor with high selectivity for mercury ions in aqueous media Styliani Voutsadaki, George K. Tsikalas, Emmanuel Klontzas, George E. Froudakis, and Haralambos E.
More informationSupporting Information
Supporting Information Wiley-VC 2008 69451 Weinheim, Germany SI-1 A Concise Approach to Vinigrol Thomas J. Maimone, Ana-Florina Voica, and Phil S. Baran* Contribution from the Department of Chemistry,
More informationHalogen bonded dimers and ribbons from the self-assembly of 3-halobenzophenones Patricia A. A. M. Vaz, João Rocha, Artur M. S. Silva and Samuel Guieu
Electronic Supplementary Material (ES) for CrystEngComm. This journal is The Royal Society of Chemistry 27 Halogen bonded dimers and ribbons from the self-assembly of -halobenzophenones Patricia A. A.
More informationSupporting Information
Supporting Information Construction of Highly Functional α-amino itriles via a ovel Multicomponent Tandem rganocatalytic Reaction: a Facile Access to α-methylene γ-lactams Feng Pan, Jian-Ming Chen, Zhe
More informationSimplified platensimycin analogues as antibacterial agents
Simplified platensimycin analogues as antibacterial agents Dragan Krsta, a Caron Ka, a Ian T. Crosby, a Ben Capuano a and David T. Manallack a * a Medicinal Chemistry and Drug Action, Monash Institute
More informationLight-Controlled Switching of a Non- Photoresponsive Molecular Shuttle
Supporting Information Light-Controlled Switching of a Non- Photoresponsive Molecular Shuttle Liu-Pan Yang, a,b Fei Jia, a Jie-Shun Cui, a Song-Bo Lu, a and Wei Jiang* a a Department of Chemistry, South
More informationSupporting Information For:
Supporting Information For: Peptidic α-ketocarboxylic Acids and Sulfonamides as Inhibitors of Protein Tyrosine Phosphatases Yen Ting Chen, Jian Xie, and Christopher T. Seto* Department of Chemistry, Brown
More informationFluorescent Chemosensor for Selective Detection of Ag + in an. Aqueous Medium
Electronic supplementary information For A Heptamethine cyanine -Based Colorimetric and Ratiometric Fluorescent Chemosensor for Selective Detection of Ag + in an Aqueous Medium Hong Zheng *, Min Yan, Xiao-Xing
More informationA TTFV pyrene-based copolymer: synthesis, redox properties, and aggregation behaviour
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 A TTFV pyrene-based copolymer: synthesis, redox properties, and aggregation behaviour Eyad
More informationTsuji Trost N-Allylation with Allylic Acetates by Using a Cellulose Palladium Catalyst
University of Nebraska - Lincoln DigitalCommons@University of Nebraska - Lincoln U.S. Environmental Protection Agency Papers U.S. Environmental Protection Agency 2012 Tsuji Trost N-Allylation with Allylic
More informationSupporting Information
An Improved ynthesis of the Pyridine-Thiazole Cores of Thiopeptide Antibiotics Virender. Aulakh, Marco A. Ciufolini* Department of Chemistry, University of British Columbia 2036 Main Mall, Vancouver, BC
More informationSelective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3
S1 Selective Reduction of Carboxylic acids to Aldehydes Catalyzed by B(C 6 F 5 ) 3 David Bézier, Sehoon Park and Maurice Brookhart* Department of Chemistry, University of North Carolina at Chapel Hill,
More informationSupplementry Information for
Supplementry Information for Cyclopropenium ion catalysed Beckmann rearrangement Vishnu P. Srivastava, Rajesh Patel, Garima and Lal Dhar S. Yadav* Department of Chemistry, University of Allahabad, Allahabad,
More informationSupporting Information. Enantioselective Organocatalyzed Henry Reaction with Fluoromethyl Ketones
Supporting Information Enantioselective Organocatalyzed Henry Reaction with Fluoromethyl Ketones Marco Bandini,* Riccardo Sinisi, Achille Umani-Ronchi* Dipartimento di Chimica Organica G. Ciamician, Università
More informationDepartment of Chemistry and Biochemistry, California State University Northridge, Northridge, CA Experimental Procedures
Supporting Information Low Temperature n-butyllithium-induced [3,3]-Sigmatropic Rearrangement/Electrophile Trapping Reactions of Allyl-1,1- Dichlorovinyl Ethers. Synthesis of - - and -lactones. Aaron Christopher
More informationSupporting Information for
Page of 0 0 0 0 Submitted to The Journal of Organic Chemistry S Supporting Information for Syntheses and Spectral Properties of Functionalized, Water-soluble BODIPY Derivatives Lingling Li, Junyan Han,
More informationMariana Gonda, Marcos Nieves, Elia Nunes, Adela López de Ceráin, Antonio Monge, María Laura Lavaggi, Mercedes González and Hugo Cerecetto
Phenazine, -dioxide scaffold as selective hypoxic cytotoxin pharmacophore. Structural modifications looking for further DA topoisomerase II-inhibition activity Mariana Gonda, Marcos ieves, Elia unes, Adela
More informationSUPPORTING INFORMATION
SUPPRTING INFRMATIN A Direct, ne-step Synthesis of Condensed Heterocycles: A Palladium-Catalyzed Coupling Approach Farnaz Jafarpour and Mark Lautens* Davenport Chemical Research Laboratories, Chemistry
More informationSupporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2017 Supporting Information Lithium Triethylborohydride-Promoted Generation of α,α-difluoroenolates
More informationHai-Bin Yang, Xing Fan, Yin Wei,* Min Shi*
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2015 Solvent-controlled Nucleophilic Trifloromethylthiolation of Morita- Baylis-Hillman
More informationAn improved preparation of isatins from indoles
An improved preparation of isatins from indoles Jiro Tatsugi,* Tong Zhiwei, and Yasuji Izawa Department of Applied Chemistry, Faculty of Engineering, Aichi Institute of Technology, Yachigusa, Yakusa-cho,
More informationAn insulin-sensing sugar-based fluorescent hydrogel
Supplementary Information An insulin-sensing sugar-based fluorescent hydrogel Sankarprasad Bhuniya and Byeang yean Kim* ational Research Laboratory, Department of Chemistry, Division of Molecular and Life
More informationSyntheses of a pillar[4]arene[1]quinone and a difunctionalized. pillar[5]arene by partial oxidation. Electronic Supplementary Information (11 pages)
Syntheses of a pillar[4]arene[1]quinone and a difunctionalized pillar[5]arene by partial oxidation Chengyou an, Zibin Zhang, Guocan Yu and Feihe uang* Department of Chemistry, Zhejiang University, angzhou
More informationSupporting Information. Sandmeyer Cyanation of Arenediazonium Tetrafluoroborate Using Acetonitrile as Cyanide Source
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2015 Supporting Information Sandmeyer Cyanation of Arenediazonium Tetrafluoroborate Using
More informationSupplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry Supplementary data
Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2012 Supplementary data Cu-catalyzed in situ generation of thiol using xanthate as thiol
More informationSupporting Information
Supporting Information An efficient and general method for the Heck and Buchwald- Hartwig coupling reactions of aryl chlorides Dong-Hwan Lee, Abu Taher, Shahin Hossain and Myung-Jong Jin* Department of
More informationMolecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe
Supporting Information for Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe Ho Yu Au-Yeung, Jefferson Chan, Teera Chantarojsiri and Christopher J. Chang* Departments
More informationSupporting Information
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 217 Supporting Information Azobenzene-Benzoylphenylureas as Photoswitchable Chitin
More informationSolid-Supported DNA for Asymmetric Synthesis: a Stepping Stone toward Practical Applications
Solid-Supported DA for Asymmetric Synthesis: a Stepping Stone toward Practical Applications Soyoung Park, * a Keiichi Ikehata, a and iroshi Sugiyama*,a,b,c a Department of Chemistry, Graduate School of
More informationSupporting Information
Supporting Information Divergent Reactivity of gem-difluoro-enolates towards Nitrogen Electrophiles: Unorthodox Nitroso Aldol Reaction for Rapid Synthesis of -Ketoamides Mallu Kesava Reddy, Isai Ramakrishna,
More informationEur. J. Org. Chem WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007 ISSN X SUPPORTING INFORMATION
Eur. J. Org. Chem. 2007 WILEY-VC Verlag Gmb & Co. KGaA, 69451 Weinheim, 2007 ISS 1434 193X SUPPORTIG IFORMATIO Title: Iron Palladium Association in the Preparation of Indoles and One-Pot Synthesis of Bis(indolyl)methanes
More informationSupplementary Materials
Supplementary Materials ORTHOGOALLY POSITIOED DIAMIO PYRROLE- AD IMIDAZOLE- COTAIIG POLYAMIDES: SYTHESIS OF 1-(3-SUBSTITUTED-PROPYL)-4- ITROPYRROLE-2-CARBOXYLIC ACID AD 1-(3-CHLOROPROPYL)-4- ITROIMIDAZOLE-2-CARBOXYLIC
More informationSynthesis and Use of QCy7-derived Modular Probes for Detection and. Imaging of Biologically Relevant Analytes. Supplementary Methods
Synthesis and Use of QCy7-derived Modular Probes for Detection and Imaging of Biologically Relevant Analytes Supplementary Methods Orit Redy a, Einat Kisin-Finfer a, Shiran Ferber b Ronit Satchi-Fainaro
More informationDerivatives. Republic. Supporting Information. Index. General Considerations. Experimental Procedures and Spectroscopic Data
Synthesis of Hexahelicene and 1-Methoxyhexahelicene via Cycloisomerization of Biphenylyl-Naphthalene Derivatives Jan Storch *, Jan Sýkora, Jan Čermák, Jindřich Karban, Ivana Císařová and Aleš Růžička Institute
More informationPhotooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins
S1 Photooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins Antonia Kouridaki, Tamsyn Montagnon, Maria Tofi and Georgios Vassilikogiannakis* Department of
More informationSUPPORTING INFORMATION. A Sensitive and Selective Ratiometric Near IR Fluorescent Probe for Zinc Ions Based on Distyryl-Bodipy Fluorophore
SUPPORTING INFORMATION A Sensitive and Selective Ratiometric Near IR Fluorescent Probe for Zinc Ions Based on Distyryl-Bodipy Fluorophore Serdar Atilgan,, Tugba Ozdemir, and Engin U. Akkaya * Department
More informationSUPPORTING INFORMATION. Fathi Elwrfalli, Yannick J. Esvan, Craig M. Robertson and Christophe Aïssa
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 SUPPORTING INFORMATION S1 Fathi Elwrfalli, Yannick J. Esvan, Craig M. Robertson and Christophe
More informationExperimental details
Supporting Information for A scalable synthesis of the (S)-4-(tert-butyl)-2-(pyridin-2-yl)-4,5-dihydrooxazole ((S)-t-BuPyx) ligand Hideki Shimizu 1,2, Jeffrey C. Holder 1 and Brian M. Stoltz* 1 Address:
More informationEfficient Pd-Catalyzed Amination of Heteroaryl Halides
1 Efficient Pd-Catalyzed Amination of Heteroaryl Halides Mark D. Charles, Philip Schultz, Stephen L. Buchwald* Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139 Supporting
More informationRegioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles by reusable
1 Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles by reusable immobilized AlCl 3 on γ-al 2 O 3 SUPPLEMETARY DATA Typical Procedure to the preparation of Azides Phenyl azide Phenyl azide was
More informationSupporting Information
Supporting Information SmI 2 -Mediated Carbon-Carbon Bond Fragmentation in α-aminomethyl Malonates Qiongfeng Xu,, Bin Cheng, $, Xinshan Ye,*, and Hongbin Zhai*,,,$ The State Key Laboratory of Natural and
More informationSupporting Information
Supporting Information Calix[4, 5]tetrolarenes: A New Family of Macrocycles Yossi Zafrani* and Yoram Cohen* School of Chemistry, The Sackler Faculty of Exact Sciences, Tel Aviv University, Ramat Aviv 69978,
More information