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1 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2019 Supporting information Bifunctional organocatalysts for conversion of C2, epoxides and aryl amines to 3-aryl-2-oxazolidinones Ya-Fei Xie, a Cheng Guo, b Lei Shi, a Bang-Hua Peng,*,a Ning Liu,*,a a School of Chemistry and Chemical Engineering, Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, North Fourth Road, Shihezi, Xinjiang , People s Republic of China; Ning Liu: ninglau@163.com; ningliu@shzu.edu.cn; Bang-Hua Peng: banghuapeng@163.com b Cancer Institute, The Second Affiliated Hospital, Zhejiang University School of Medicine, Hangzhou, Zhejiang , People s Republic of China 78 Figures 1. Synthesis and Characterization for rganocatalysts...s Synthesis of 3-Aryl-2-xazolidinones S5 3. NMR and IR Spectra for 3-Aryl-2-xazolidinones S NMR Spectra for rganocatalysts......s37-44 S1
2 1. Synthesis and Characterization for rganocatalysts General Procedure for Synthesis of rganocatalysts A mixture of 2,6-dibromopyridine (5 mmol), amines (10 mmol), CuI (1 mmol), tetra-methylethane-1,2-diamine (2 mmol) and K2C3 (15 mmol) in DMS (20 ml) was stirred for 30 min at room temperature, and then heated to 90 C for 24 h under nitrogen atmosphere. Thereafter, 2-bromo-6-substituent-pyridine (5 mmol), amino acids (7.5 mmol), CuI (1 mmol), N,N-dimethylethylenediamine (2 mmol) and K2C3 (15 mmol) in DMS (20 ml) was allowed to react under nitrogen atmosphere. The resultant 2,6-disubstituent-pyridine (5 mmol), and alkyl halides (10 ml) was heated to the desired temperature and the reaction stirred for 8 h under air atmosphere, and affording a series of multifunctional organocatalysts 1a g. The solvent was concentrated under vacuum and the product of organocatalysts 1a g was isolated by flash chromatography. Characterization for rganocatalysts Data for 1a are as follows: Purification by flash chromatography (DCM/MeH = 20:1): a yellowish solid (1.468 g, 61%), M.P. = C; 1 H NMR (400 MHz, DMS-d6): δ (br., 1H, CH), (s, 1H, NCHN), 8.39 (d, J = 8.0 Hz, 1H), 8.20 (d, J = 7.2 Hz, 1H), (m, 3H), 7.47 (d, J = 8.0 Hz, NH), 7.08 (d, J = 7.2 Hz, 1H), 6.96 (d, J = 7.6 Hz, 1H), 4.55 (t, J = 6.8 Hz, 2H), 4.33 (t, J = 5.6 Hz, 1H), 2.23 (sext, J = 6.8 Hz, 1H), 2.02 (sext, J = 7.2 Hz, 2H), (m, 9H), ppm; 13 C NMR (100 MHz, DMS-d6): δ , , , , , , , , , , , , 59.74, 49.04, 30.33, 22.50, 19.80, 18.85, 11.26, ppm; HRMS (MALDI) calcd for C20H25N42I [M-I] , found Data for 1b are as follows: Purification by flash chromatography (DCM/MeH = 25:1): a yellowish solid (1.227 g, 49%), M.P. = C; 1 H NMR (400 MHz, DMS-d6): δ (br., 1H, CH), (s, 1H, NCHN), 8.37 (d, J = 8.0 Hz, 1H), 8.19 (d, J = 7.6 Hz, 1H), (m, 3H), 7.62 (d, J = 8.0 Hz, NH), 7.06 (d, J = 7.2 S2
3 Hz, 1H), 6.83 (d, J = 7.6 Hz, 1H), 4.53 (t, J = 7.6 Hz, 2H), (m, 1H), 2.02 (sext, J = 7.6 Hz, 2H), (m, 2H), (m, 6H), 0.88 (d, J = 6.4 Hz, 3H), ppm; 13 C NMR (100 MHz, DMS-d6): δ , , , , , , , , , , , , 52.65, 49.04, 24.98, 23.36, 22.47, 21.81, 11.27, ppm; HRMS (MALDI) calcd for C21H27N42I [M-I] , found Data for 1c are as follows: Purification by flash chromatography (DCM/MeH = 15:1): a yellowish solid (0.905 g, 35%), M.P. = C; 1 H NMR (400 MHz, DMS-d6): δ (br., 1H, CH), (s, 1H, NCHN), 8.40 (d, J = 8.0 Hz, 1H), 8.20 (d, J = 8.0 Hz, 1H), (m, 3H), 7.67 (d, J = 8.0 Hz, NH), 7.09 (d, J = 8.0 Hz, 1H), 6.84 (d, J = 8.0 Hz, 1H), (m, 3H), (m, 2H), (m, 6H), 1.00 (t, J = 7.6 Hz, 3H), ppm; 13 C NMR (100 MHz, DMS-d6): δ , , , , , , , , , , , , 53.06, 49.05, 31.18, 30.38, 22.48, 14.97, 11.27, ppm; HRMS (MALDI) calcd for C20H25N42SI [M-I] , found Data for 1d are as follows: Purification by flash chromatography (DCM/MeH = 10:1): a yellowish solid (1.309 g, 49%), M.P. = C; 1 H NMR (400 MHz, DMS-d6): δ (br., 1H, CH), (s, 1H, NCHN), 8.28 (d, J = 8.0 Hz, 1H), 8.19 (d, J = 8.0 Hz, 1H), (m, 3H), 7.71 (d, J = 8.0 Hz, NH), (m, 4H), 7.18 (t, J = 7.6 Hz, 1H), 7.04 (d, J = 7.2 Hz, 1H), 6.82 (d, J = 8.4 Hz, 1H), (m, 1H), 4.52 (t, J = 7.6 Hz, 2H), 3.22 (dd, J = 14.0 Hz, 4.8 Hz, 1H), 3.02 (dd, J = 14.0 Hz, 4.8 Hz, 1H), 2.01 (sext, J = 7.6 Hz, 2H), 0.99 (t, J = 7.6 Hz, 3H), ppm; 13 C NMR (100 MHz, DMS-d6): δ , , , , , , , , , , , , , , , , 55.91, 49.02, 37.53, 22.49, 11.25, ppm; HRMS (MALDI) calcd for C24H25N42I [M-I] , found Data for 1e are as follows: Purification by flash chromatography (DCM/MeH = 40:1): a yellowish solid (1.671 g, 61%), M.P. = C; 1 H NMR (400 MHz, DMS-d6): δ (br., 1H, CH), (s, 1H, NCHN), 9.19 (s, 1H, H), 8.28 (d, J = 8.0 Hz, 1H), 8.20 (d, J = 8.0 Hz, 1H), (m, 3H), 7.65 (d, J = 8.0 Hz, NH), S3
4 7.11 (d, J = 8.0 Hz, 2H), 7.06 (d, J = 8.0 Hz, 1H), 6.84 (d, J = 8.0 Hz, 1H), 6.66 (d, J = 8.0 Hz, 2H), (m, 3H), 3.09 (dd, J = 14.0 Hz, 4.8 Hz, 1H), (m, 1H), 2.02 (sext, J = 7.6 Hz, 2H), 0.99 (t, J = 7.6 Hz, 3H), ppm; 13 C NMR (100 MHz, DMS-d6): δ , , , , , , , , , , , , , , , , 56.55, 49.05, 36.89, 22.50, 11.25, ppm; HRMS (MALDI) calcd for C24H25N43I [M-I] , found Data for 1f are as follows: Purification by flash chromatography (DCM/MeH = 25:1): a yellowish solid (1.056 g, 50%), M.P. = C; 1 H NMR (400 MHz, DMS-d6): δ (s, 1H, NCHN), 9.20 (s, 1H, H), 8.30 (d, J = 8.0 Hz, 1H), 8.19 (d, J = 8.0 Hz, 1H), (m, 3H), 7.61 (d, J = 8.0 Hz, NH), 7.10 (d, J = 8.0 Hz, 2H), 7.03 (d, J = 8.0 Hz, 1H), 6.82 (d, J = 8.0 Hz, 1H), 6.64 (d, J = 8.0 Hz, 2H), (m, 3H), 3.10 (dd, J = 14.0 Hz, 4.8 Hz, 1H), (m, 1H), 2.01 (sext, J = 7.6 Hz, 2H), 0.99 (t, J = 7.6 Hz, 3H), ppm; 13 C NMR (100 MHz, DMS-d6): δ , , , , , , , , , , , , , , , , 56.42, 49.00, 36.87, 22.49, 11.24, ppm; HRMS (MALDI) calcd for C24H25N43Br [M-Br] , found Data for 1g are as follows: Purification by flash chromatography (DCM/MeH = 20:1): a yellowish solid (0.972 g, 46%), M.P. = C; 1 H NMR (400 MHz, DMS-d6): δ (s, 1H, NCHN), 8.37 (d, J = 8.0 Hz, 1H), 8.14 (d, J = 8.0 Hz, 1H), (m, 3H), 7.47 (s, NH), 7.06 (d, J = 8.0 Hz, 2H), 7.00 (d, J = 8.0 Hz, 1H), 6.77 (d, J = 8.0 Hz, 1H), 6.61 (d, J = 8.0 Hz, 2H), 4.52 (t, J = 7.6 Hz, 3H), 3.10 (dd, J = 14.0 Hz, 4.8 Hz, 1H), (m, 1H), 1.98 (sext, J = 7.6 Hz, 2H), 0.99 (t, J = 7.6 Hz, 3H), ppm; 13 C NMR (100 MHz, DMS-d6): δ , , , , , , , , , , , , , , , , 57.49, 48.92, 37.20, 22.51, 11.21, ppm; HRMS (MALDI) calcd for C24H25N43Cl [M-Cl] , found S4
5 2. Synthesis of 3-Aryl-2-xazolidinones General procedure for the synthesis of 3-aryl-2-oxazolidinones Epoxides (2.0 ml), aryl amines (2.0 mmol), organocatalyst (0.05 mmol), and DBU (0.4 mmol) were introduced into a 25 ml stainless steel autoclave that was equipped with a magnetic stirrer. The reactor was pressurized with C2 to 0.5 MPa and then heated at 90 C for the required time. The reactor was cooled to room temperature after the reaction. The reaction mixtures were added to brine (15 ml) and extracted three times with dichloromethane (3 15 ml). The solvent was removed under reduced pressure, and the products were isolated by flash chromatography. S5
6 3. NMR and IR Spectra for N-aryl-2-oxazolidinones Figure S1. 1 H NMR spectra of oxazolidinones 4a. Figure S2. 13 C NMR spectra of oxazolidinones 4a. S6
7 N Transmittance (%) Wavelength (cm -1 ) Figure S3. IR spectroscopic data of oxazolidinones 4a. Figure S4. 1 H NMR spectra of oxazolidinones 4b. S7
8 Figure S5. 13 C NMR spectra of oxazolidinones 4b. N CH Transmittance (%) Wavelength (cm -1 ) Figure S6. IR spectroscopic data of oxazolidinones 4b. S8
9 Figure S7. 1 H NMR spectra of oxazolidinones 4c. Figure S8. 13 C NMR spectra of oxazolidinones 4c. S9
10 N Transmittance (%) Wavelength (cm -1 ) Figure S9. IR spectroscopic data of oxazolidinones 4c. Figure S10. 1 H NMR spectra of oxazolidinones 4d. S10
11 Figure S C NMR spectra of oxazolidinones 4d. N C 2 H Transmittance (%) Wavelength (cm -1 ) Figure S12. IR spectroscopic data of oxazolidinones 4d. S11
12 Figure S13. 1 H NMR spectra of oxazolidinones 4e. Figure S C NMR spectra of oxazolidinones 4e. S12
13 Figure S F NMR spectra of oxazolidinones 4e. N F Transmittance (%) Wavelength (cm -1 ) Figure S16. IR spectroscopic data of oxazolidinones 4e. S13
14 Figure S17. 1 H NMR spectra of oxazolidinones 4f. Figure S C NMR spectra of oxazolidinones 4f. S14
15 N Cl Transmittance (%) Wavelength (cm -1 ) Figure S19. IR spectroscopic data of oxazolidinones 4f. Figure S20. 1 H NMR spectra of oxazolidinones 4g. S15
16 Figure S C NMR spectra of oxazolidinones 4g. N Br Transmittance (%) Wavelength (cm -1 ) Figure S22. IR spectroscopic data of oxazolidinones 4g. S16
17 Figure S23. 1 H NMR spectra of oxazolidinones 4h. Figure S C NMR spectra of oxazolidinones 4h. S17
18 N I 100 Transmittance (%) Wavelength (cm -1 ) Figure S25. IR spectroscopic data of oxazolidinones 4h. Figure S26. 1 H NMR spectra of oxazolidinones 4i. S18
19 Figure S C NMR spectra of oxazolidinones 4i. N Transmittance (%) Wavelength (cm -1 ) Figure S28. IR spectroscopic data of oxazolidinones 4i. S19
20 Figure S29. 1 H NMR spectra of oxazolidinones 4j. Figure S C NMR spectra of oxazolidinones 4j. S20
21 N 2 N Transmittance (%) Wavelength (cm -1 ) Figure S31. IR spectroscopic data of oxazolidinones 4j. Figure S32. 1 H NMR spectra of oxazolidinones 4k. S21
22 Figure S C NMR spectra of oxazolidinones 4k. Cl N Cl Transmittance (%) Wavelength (cm -1 ) Figure S34. IR spectroscopic data of oxazolidinones 4k. S22
23 Figure S35. 1 H NMR spectra of oxazolidinones 4l. Figure S C NMR spectra of oxazolidinones 4l. S23
24 N Transmittance (%) Wavelength (cm -1 ) Figure S37. IR spectroscopic data of oxazolidinones 4l. Figure S38. 1 H NMR spectra of oxazolidinones 4m. S24
25 Figure S C NMR spectra of oxazolidinones 4m. N Transmittance (%) Wavelength (cm -1 ) Figure S40. IR spectroscopic data of oxazolidinones 4m. S25
26 Figure S41. 1 H NMR spectra of oxazolidinones 4n. Figure S C NMR spectra of oxazolidinones 4n. S26
27 N Transmittance (%) Wavelength (cm -1 ) Figure S43. IR spectroscopic data of oxazolidinones 4n. Figure S44. 1 H NMR spectra of oxazolidinones 4o. S27
28 Figure S C NMR spectra of oxazolidinones 4o Transmittance (%) Wavelength (cm -1 ) Figure S46. IR spectroscopic data of oxazolidinones 4o. S28
29 Figure S47. 1 H NMR spectra of oxazolidinones 4p. Figure S C NMR spectra of oxazolidinones 4p. S29
30 N Transmittance (%) Wavelength (cm -1 ) Figure S49. IR spectroscopic data of oxazolidinones 4p. Figure S50. 1 H NMR spectra of oxazolidinones 4q. S30
31 Figure S C NMR spectra of oxazolidinones 4q. N Transmittance (%) Wavelength (cm -1 ) Figure S52. IR spectroscopic data of oxazolidinones 4q. S31
32 Figure S53. 1 H NMR spectra of oxazolidinones 4r. Figure S C NMR spectra of oxazolidinones 4r. S32
33 Transmittance (%) Wavelength (cm -1 ) Figure S55. IR spectroscopic data of oxazolidinones 4r. Figure S56. 1 H NMR spectra of oxazolidinones 4s. S33
34 Figure S C NMR spectra of oxazolidinones 4s. N 100 Cl Transmittance (%) Wavelength (cm -1 ) Figure S58. IR spectroscopic data of oxazolidinones 4s. S34
35 Figure S59. 1 H NMR spectra of oxazolidinones 4t. Figure S C NMR spectra of oxazolidinones 4t. S35
36 Figure S61. 1 H NMR spectra of oxazolidinones 4u. Figure S C NMR spectra of oxazolidinones 4u. S36
37 4. NMR Spectra for rganocatalysts Figure S63. 1 H NMR spectra of organocatalyst 1a. Figure S C NMR spectra of organocatalyst 1a. S37
38 Figure S65. 1 H NMR spectra of organocatalyst 1b. Figure S C NMR spectra of organocatalyst 1b. S38
39 Figure S67. 1 H NMR spectra of organocatalyst 1c. Figure S C NMR spectra of organocatalyst 1c. S39
40 Figure S69. 1 H NMR spectra of organocatalyst 1d. Figure S C NMR spectra of organocatalyst 1d. S40
41 Figure S71. 1 H NMR spectra of organocatalyst 1e. Figure S C NMR spectra of organocatalyst 1e. S41
42 Figure S73. 1 H NMR spectra of organocatalyst 1f. Figure S C NMR spectra of organocatalyst 1f. S42
43 Figure S75. 1 H NMR spectra of organocatalyst 1g. Figure S C NMR spectra of organocatalyst 1g. S43
44 Figure S77. 1 H NMR spectra of organocatalyst 1h. Figure S C NMR spectra of organocatalyst 1h. S44
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