Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes

Transcription

1 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, Shanghi Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai, , China Supporting Information List of contents Experiment procedures..s2 Characterization data: 3 and 4,...S3-S11 1 H NMR, 13 C NMR and IR spectra...s12-s65 X-ray crystal structure of 3e..S66 S1

2 1. Experiment procedures All reactions were performed under air atmosphere. Solvents were used without purification. Petroleum ether refers to the fraction with boiling point in the range C. All 1 H NMR and 13 C NMR spectra were measured in CDCl3 or DMSO-d 6 with TMS as the internal standard. Chemical shifts are expressed in ppm and J values are given in Hz. High resolution mass spectra were recorded on a Finnigan MAT 95 mass spectrometer (EI) or IonSpec 4.7 Tesla FTMS (ESI). Column chromatography was performed with mesh silica gel using flash column techniques. Melting points are uncorrected. All microwave irradiation reactions were conducted by using CEM microwave reactor. Compounds 2 were prepared according to the reported method. 1, 2 General Procedure: A typical procedure for the preparation of 3a: To the solution of 1a (52 mg, 0.2 mmol) and 2a (49 mg, 0.2 mmol) in THF (1.5 ml) in a 10 ml microwave vial containing a magnetic stir bar was added DBU (60 µl, 0.4 mmol). The reaction vessel was sealed and heated in a microwave reactor at 100 ºC for 10 min. After cooling, the resulting mixture was diluted with water (20 ml) and extracted with ethyl acetate (15 ml 3) and the combined organic layers were washed with brine (10 ml), dried over anhydrous Na 2 SO 4, filtered and concentrated to give the crude product, which was further purified by column chromatography (petroleum ether/ethyl acetate 10:1 to petroleum ether/ethyl acetate 4:1) to afford compound 3a as a light yellow solid. A typical procedure for the preparation of 4a: To the solution of 1a (52 mg, 0.2 mmol) and 2j (49 mg, 0.2 mmol) in THF (1.5 ml) in a 10 ml round-bottom flask containing a magnetic stir bar was added base (0.4 mmol). The reaction vessel was heated in oil bath at 100 ºC for 2h. After cooling, the resulting mixture was diluted with water (20 ml) and extracted with ethyl acetate (15 ml 3) and the combined organic layers were washed with brine (10 ml), dried over anhydrous Na 2 SO 4, filtered and concentrated to give the crude product, which was further purified by column chromatography (petroleum ether/ethyl acetate 10:1 to petroleum ether/ethyl acetate 4:1) to afford compound 3a as a light yellow solid. S2

3 2. Characterization Data: As a yellow solid: m.p o C; IR (KBr) ν max 2922, 2852, 1641, 1626, 1614, 1585, 1485, 1469, 1415, 1304, 1223, 1151, 931, 756, 712 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ (s, 1H), (d, J = 9.0 Hz, 1H), 8.47 (d, J = 7.9 Hz, 1H), 8.28 (s, 1H), 8.05 (d, J =8.9 Hz, 1H), 7.77 (t, J = 3.6 Hz, 1H), (m, 10H), 7.06 (d, J = 8.1 Hz, 1H), 6.87 ppm (t, J = 7.6 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ): δ 201.0, 177.9, 163.2, 157.9, 154.7, 149.6, 138.1, 136.4, 135.0, 134.3, 134.0, 133.5, 129.6, , , , 128.4, 128.2, 127.2, 126.7, 124.7, 123.6, 119.9, 119.1, 118.6, 118.4, 117.6, ppm; HRMS calcd for C 30 H 19 O 4 : , found: As a white solid: m.p o C; IR (KBr) ν max 3425, 3070, 1643, 1620, 1603, 1589, 1504, 1469, 1421, 1327, 1306, 1217, 876, 762 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ (s, 1H), (d, J = 9.0 Hz 1H), (m, 2H), 8.04 (dd, J =8.9,1.8 Hz, 1H), 7.76 (dt, J = 7.2,1.6 Hz, 1H), 7.68 (dd, J = 8.0, 1.6 Hz, 1H), (m, 3H), 7.48 (dt, J = 8.0, 0.9 Hz, 1H), 7.13 (dd, J = 8.4, 0.9 Hz 1H), 6.92 (dt, J = 8.0, 1.0 Hz, 1H), 2.85 ppm (d, J = 0.8, 3H); 13 C NMR (100 MHz, CDCl 3 ): δ 201.3, 178.0, 163.3, 158.4, 154.6, 145.2, 136.5, 135.0, 134.1, 133.7, 133.6, 129.1, 128.8, 127.4, 126.7, 125.8, 124.6, 123.6, 119.7, 119.3, 118.8, 118.5, 117.6, 113.2, 20.4 ppm; HRMS calcd for C 25 H 17 O 4 (M+H) + : , found: S3

4 As a yellow solid: m.p o C; IR (KBr) ν max 3431, 2962, 1649, 1608, 1514, 1468, 1442, 1398, 1306, 1255, 1153, 1032, 931, 758 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ (s, 1H), (d, J = 8.9 Hz, 1H), 8.47 (d, J = 8.2 Hz, 1H), 8.34 (s, 1H), 8.04 (d, J = 8.9 Hz, 1H), 7.77 (t, J = 7.7 Hz, 1H), (m, 7H), (m, 3H), 6.88 (t, J = 7.6 Hz, 1H), 3.90 ppm (s, 3H); 13 C NMR (100 MHz, CDCl 3 ): δ 201.1, 178.0, 163.3, 160.1, 158.0, 154.7, 149.5, 136.4, 135.0, 134.2, 134.1, 133.6, 130.9, 130.4, 128.8, 128.5, 127.2, 126.8, 124.7, 123.7, 119.7, 119.2, 118.7, 118.5, 117.6, 114.2, 113.4, 55.4 ppm; HRMS calcd for C 31 H 21 O 5 (M+H) + : , found: As a yellow solid: m.p o C; IR (KBr) ν max 2956, 2924, 2854, 1647, 1610, 1581, 1527, 1466, 1444, 1373, 1304, 1219, 1151, 822, 758 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ (s, 1H), (d, J = 8.9 Hz 1H), 8.48 (m, 2H), 8.04 (dd, J = 8.9, 1.7 Hz, 1H), 7.77 (t, J = 7.2 Hz, 1H), 7.66 (dd, J = 8.1, 1.5 Hz, 1H), (m, 6H), 7.08 (d, J = 8.0 Hz, 1H), (m, 3H), 3.05 ppm (s, 6H); 13 C NMR (100 MHz, CDCl 3 ): δ 201.3, 178.0, 163.2, 158.3, 154.8, 150.7, 136.3, 134.9, 134.3, 134.1, 133.7, 130.7, 128.8, 128.7, 128.6, 127.1, 126.8, 125.7, 124.5, 123.8, 119.3, 119.1, 118.7, 118.4, 117.5, 113.0, 112.2, 40.3 ppm; HRMS calcd for C 32 H 24 NO 4 (M+H) + : , found: S4

5 As a white solid: m.p o C; IR (KBr) ν max 2962, 1645, 1612, 1587, 1466, 1442, 1415, 1302, 1223, 1153, 1107, 1034, 930, 816, 758 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ (s, 1H), (d, J = 8.9 Hz, 1H), 8.47 (d, J = 8.1 Hz, 1H), 8.32 (s, 1H), 8.04 (d, J = 8.8, 0.8 Hz, 1H), 7.78 (t, J = 4.1 Hz, 1 H), (m, 7H), (m, 2H), 7.06 (d, J = 8.7 Hz, 1H), 6.88(t, J = 7.5Hz, 2H), 2.45 ppm (s, 3H) ; 13 C NMR (100 MHz, CDCl 3 ): δ 201.1, 178.0, 163.3, 158.0, 154.7, 149.8, 138.8, 136.4, 135.3, 135.0, 134.2, 134.0, 133.6, 129.5, 129.4, 128.8, 128.5, 128.3, 127.2, 126.8, 124.7, 123.7, 119.8, 119.2, 118.7, 118.4, 117.6, 113.5, 21.3 ppm; HRMS calcd for C 31 H 21 O 4 (M+H) + : , found: As a yellow solid: m.p o C; IR (KBr) ν max 3066, 1693, 1639, 1614, 1468, 1325, 1157, 1117, 1066, 847, 760 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ (s, 1H), (d, J = 9.0 Hz, 1H), 8.49 (dd, J = 8.0, 1.6 Hz, 1H), 8.17 (d, J = 2.0 Hz, 1H), 8.07 (dd, J = 8.6, 1.7 Hz, 1H), (m, 3H), (m, 7H), 7.07 (d, J = 7.9 Hz, 1H), 6.87 ppm (t, J = 7.5 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 200.9, 178.0, 163.3, 154.7, 141.8, 136.6, 135.4, 134.5, 134.1, 133.9, 133.4, 130.0, 129.1, 127.9, 127.7, 127.3, 126.8, 125.8, 125.8, 124.9, 123.6, 120.2, 119.0, 118.7, 118.6, 118.6, 117.7, 117.6, ppm; HRMS calcd for C 31 H 18 F 3 O 4 (M+H) + : , found: S5

6 As a yellow solid: m.p o C; IR (KBr) ν max 3440, 2924, 1693, 1641, 1614, 1587, 1560, 1466, 1388, 1304, 1221, 1151, 841, 758 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ (s, 1H), (d, J = 8.6 Hz, 1H), 8.48 (dd, J = 8.0, 1.6 Hz, 1H), 8.23 (d, J = 1.8 Hz, 1H), 8.06 (dd, J = 9.1, 1.8 Hz, 1H), 7.79 (dt, J = 7.8, 1.7 Hz, 1H), (m, 7H), (m, 2H), 7.07 (d, J = 8.5 Hz, 1H), 6.87 ppm (t, J = 7.2 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ): δ 200.8, 177.8, 163.8, 163.3, 162.2, 157.7, 154.6, 148.4, 136.5, 135.1, 134.3, 134.1, 133.9, 133.4, , , 128.9, 128.2, 128.1, 127.2, 126.7, 124.7, 123.6, 120.0, 119.1, 118.6, 118.5, 117.5, 115.9, 115.8, ppm; HRMS calcd for C 30 H 18 FO 4 (M+H) + : , found: As a yellow solid: m.p o C; IR (KBr) ν max 3429, 3062, 1720, 1647, 1612, 1485, 1466, 1304, 1219, 1153, 1009, 930, 829, 756 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ): δ (s, 1H), (d, J = 8.8 Hz, 1H), 8.46 (dd, J = 8.1, 1.3 Hz, 1H), 8.22 (d, J = 1.9 Hz, 1H), 8.04 (dd, J = 8.6, 1.8 Hz, 1H), 7.78 (t, J = 7.8 Hz, 1H), 7.68 (d, J = 8.0 Hz, 2H), (m, 7H), 7.08 (d, J = 8.2 Hz, 1H), 6.88 ppm (t, J = 7.5 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ): δ 200.9, 177.9, 163.3, 157.8, 154.7, 148.2, 137.1, 136.6, 135.3, 134.4, 134.0, 133.5, 132.0, 131.2, 129.0, 128.0, 127.9, 127.3, 126.8, 124.8, 123.7, 123.3, 120.0, 119.1, 118.7, 118.6, 117.6, ppm; HRMS calcd for C 30 H 18 BrO 4 (M+H) + : , found: S6

7 As a yellow solid: m.p o C; IR (KBr) ν max 3109, 1649, 1624, 1610, 1589, 1514, 1466, 1417, 1348, 1306, 1155, 931, 854, 766 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ) δ (s, 1H), (d, J = 8.8 Hz, 1H), 8.48 (d, J = 8.0 Hz, 1H), 8.42 (d, J = 8.3 Hz, 2H), 8.08 (dd, J = 10.9, 1.8 Hz, 2H), (m, 3H), 7.66 (s, 1H), 7.55 (dt, J = 15.2, 8.2 Hz, 4H), 7.08 (d, J = 8.4 Hz, 1H), 6.88 (t, J = 7.6 Hz, 1H). 13 C NMR (100 MHz, CDCl 3 ) δ 200.7, 177.9, 163.3, 157.5, 154.7, 148.0, 146.7, 144.7, 136.7, 135.6, 133.9, 134.6, 133.3, 130.6, 129.3, 127.6, 127.4, 127.4, 126.8, 125.0, 124.0, 123.6, 120.3, 119.0, 118.7, 118.6, 117.6, ppm. HRMS calcd for C 30 H 17 NO 6 M + : , found: As a yellow solid: m.p o C. IR (KBr) ν max 3423, 3053, 2924, 1641, 1626, 1612, 1583, 1485, 1469, 1415, 1329, 1304, 1223, 1159, 916, 758, 706 cm -1 ; 1 H NMR (500 MHz, CDCl 3 ) δ (s, 1H), (d, J = 8.9 Hz, 0.48H), 8.49 (dd, J = 8.0, 1.5 Hz, 1H), 8.29 (d, J = 1.8 Hz, 1H), 8.06 (td, J = 4.5, 1.9 Hz, 1H), 7.78 (ddd, J = 8.6, 7.2, 1.6 Hz, 1H), 7.65 (s, 0.38H), 7.62 (dd, J = 8.0, 1.5 Hz, 1H), (m, 8H), (m, 1H), ppm (m, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ = 201.0, 178.0, 163.2, 157.9, 154.7, 149.6, 138.1, 136.4, 135.0, 134.3, 133.5, 129.6, 128.9, 128.8, 128.2, 128.8, 128.7, 127.2, 126.8, 124.7, 123.6, 119.9, 119.1, 118.7, 118.7, 118.4, 117.6, ppm. HRMS calcd for C 30 H 16 D 2 O 4 (M+Na) + : , found: S7

8 As a yellow solid: m.p o C; IR (KBr) ν max 2979, 1724, 1641, 1626, 1603, 1577, 1466, 1398, 1363, 1294, 1230, 1169, 1084, 1020, 972, 760 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ) δ (s, 1H), 8.39 (d, J = 1.8 Hz, 1H), 8.22 (dd, J = 8.0, 1.3 Hz, 1H), 7.88 (dd, J = 7.9, 1.9 Hz, 1H), 7.68 (m, 2H), (dt, J = 8.0, 1.5 Hz, 1H), 7.48 (d, J = 8.5 Hz, 1H), 7.40 (m, 2H), 7.10 (d, J = 8.4 Hz, 1H), (dt, J = 7.6, 1.1 Hz, 1H), 4.19 (q, J = 7.1 Hz, 2H), 2.28 (s, 3H), 1.14 (t, J = 7.1 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 200.3, 176.3, 165.7, 163.3, 161.9, 156.0, 138.0, 137.7, 136.8, 133.6, 133.5, 132.3, 132.2, 131.8, 131.3, 126.2, 124.9, 123.2, 122.9, 119.0, 118.8, 118.5, 117.7, 61.3, 19.5, 13.7 ppm. HRMS calcd for C 26 H 20 O 6 M + : , found: As a yellow solid: m.p o C; IR (KBr) ν max 3404, 3060, 2227, 1649, 1633, 1599, 1481, 1462, 1398, 1367, 1302, 1225, 978, 760 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ) δ (s, 1H), 8.25 (d, J = 8.0 Hz, 1H), 8.09 (s, 1H), 7.98 (d, J = 8.5 Hz, 1H), 7.73 (d, J = 8.4 Hz, 1H), (m, 5H), 7.12 (d, J = 8.4 Hz, 1H), 6.96 (t, J = 7.6 Hz, 1H), 2.39 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 198.7, 175.6, 164.6, 163.3, 155.9, 140.6, 138.0, 137.2, 134.1, 133.4, 133.0, 132.3, 126.2, 125.5, 122.9, 120.0, 119.2, 118.7, 118.4, 117.8, 116.8, 114.7, 19.6 ppm. HRMS calcd for C 24 H 15 NO 4 M + : , found: As a yellow solid: m.p o C; IR (KBr) ν max 2914, 1641, 1628, 1614, 1579, 1487, 1446, 1338, 1265, 1238, 1211, 1146, 953, 752 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ) δ (s, 1H), 8.25 (dd, J = 8.0, 1.4 Hz, 1H), (m, 3H), 7.65 (ddd, J = 8.8, 7.2, 1.7 Hz, 1H), (m, 1H), (m, 1H), (m, 2H), (m, 3H), (m, 2H), 7.08 (d, J = 8.4 Hz, 1H), (m, 1H), 1.93 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ , 177.2, 163.4, 163.2, 155.8, 142.9, 140.1, 137.9, S8

9 136.5, 135.7, 133.8, 133.5, 131.8, 130.8, 128.9, 128.3, 128.1, 127.4, 126.2, 125.0, 122.9, 122.6, 119.0, 118.8, 118.3, 117.7, 19.3 ppm. HRMS calcd for C 29 H 20 O 4 M + : , found: As a yellow solid: m.p o C; IR (KBr) ν max 2837, 1633, 1622, 1608, 1595, 1574, 1516, 1462, 1394, 1361, 1282, 1228, 1196, 1109, 1030, 955, 835, 764 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ) δ (s, 1H), (m, 1H), 7.76 (dd, J = 9.4, 1.4 Hz, 2H), 7.70 (dd, J = 7.8, 1.7 Hz, 1H), (m, 1H), 7.52 (t, J = 7.8 Hz, 1H), 7.43 (d, J = 7.8 Hz, 2H), (m, 1H), (m, 2H), 7.08 (d, J = 8.4 Hz, 1H), 6.90 (t, J = 7.6 Hz, 1H), 6.79 (t, J = 5.8 Hz, 2H), 3.75 (s, 3H), 1.93 (s, 3H). 13 C NMR (101 MHz, cdcl 3 ) δ 201.3, 177.2, 163.4, 163.2, 158.9, 155.9, 142.6, 137.9, 136.4, 135.7, 133.8, 133.5, 132.5, 131.7, 130.7, 129.7, 127.8, 126.2, 124.9, 122.9, 122.7, 119.1, 118.8, 118.3, 117.7, 113.7, 55.1, 19.3 ppm. HRMS calcd for C 29 H 20 O 4 M + : , found: As a yellow solid: m.p o C; IR (KBr) ν max 3423, 3074, 1732, 1633, 1604, 1576, 1514, 1464, 1402, 1348, 1234, 1109, 949, 860, 758, 708 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ) δ (s, 1H), 8.19 (d, J = 7.9 Hz, 1H), 8.12 (d, J = 8.5 Hz, 2H), (m, 2H), 7.72 (d, J = 8.2 Hz, 1H), 7.66 (d, J = 8.1 Hz, 1H), 7.55 (d, J = 7.2 Hz, 1H), 7.49 (dd, J = 8.3, 4.1 Hz, 3H), 7.41 (t, J = 8.6 Hz, 2H), 7.10 (d, J = 8.4 Hz, 1H), 6.92 (t, J = 7.6 Hz, 1H), 2.03 (s, 3H).. 13 C NMR (101 MHz, cdcl 3 ) δ 200.6, 176.8, 163.5, 163.3, 155.8, 147.2, 146.9, 140.9, 138.3, 136.8, 135.7, 133.9, 133.5, 132.0, 130.4, 129.5, 129.4, 126.1, 125.3, 123.6, 122.7, 122.1, 118.9, 118.5, 117.8, 19.4 ppm. HRMS calcd for C 29 H 20 O 4 M + : , found: S9

10 As a yellow solid: m.p o C; IR (KBr) ν max 3047, 1676, 1633, 1604, 1574, 1529, 1462, 1375, 1352, 1302, 1242, 1155, 928, 768 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ) δ (s, 1H), (d, J = 9.0 Hz, 1H), (m, 3H), 8.27 (dd, J = 22.3, 9.7 Hz, 2H), 8.02 (d, J = 8.6 Hz, 2H), 7.85 (t, J = 7.8 Hz, 1H), 7.73 (d, J = 8.2 Hz, 1H), 7.56 (t, J = 6.7 Hz, 3H), 7.11 (d, J = 8.8 Hz, 1H), 6.91 (t, J = 7.6 Hz, 1H). 13 C NMR (100 MHz, CDCl 3 ) δ 199.7, 194.0, 175.2, 163.3, 156.3, 153.6, 150.1, 141.6, 138.8, 137.4, 137.3, 137.0, 134.8, 134.2, 133.0, 132.0, 131.4, 130.9, 129.3, 126.3, 125.6, 124.4, 123.7, 123.5, 118.9, 118.7, ppm. HRMS calcd for C 29 H 17 NO 7 M + : , found: As a yellow solid: m.p o C; IR (KBr) ν max 3257, 3084, 1718, 1678, 1624, 1608, 1545, 1572, 1522, 1485, 1385, 1352, 1240, 1215, 1165, 1080, 982, 850, 758 cm -1 ; 1 H NMR (500 MHz, Acetone) δ (s, 1H), 8.92 (d, J = 8.3 Hz, 1H), 8.34 (d, J = 8.9 Hz, 2H), 8.07 (d, J = 8.9 Hz, 2H), 8.01 (dd, J = 7.9, 1.1 Hz, 1H), 7.92 (dd, J = 8.3, 1.7 Hz, 1H), (m, 1H), (m, 1H), 7.51 (dd, J = 8.0, 1.3 Hz, 1H), (m, 3H), 7.15 (br, 1H),7.02 (d, J = 8.3 Hz, 1H), 6.89 (t, J = 7.6 Hz, 1H). 13 C NMR (126 MHz, Acetone) δ 199.5, 199.4, 162.5, 162.2, 159.1, 153.3, 148.5, 147.5, 136.8, 136.3, 136.3, 133.4, 132.9, 132.2, 130.3, 128.5, 127.4, 125.0, 124.4, 123.6, 123.3, 119.3, 118.8, 117.9, 117.8, 116.3, 115.3, ppm. HRMS calcd for C 29 H 17 NO 8 M + : , found: S10

11 As a yellow solid: m.p o C; IR (KBr) ν max 3429, 3113, 2920, 1736, 1651, 1614, 1545, 1466, 1425, 1352, 1304, 1223, 1153, 766 cm -1 ; 1 H NMR (300 MHz, CDCl 3 ) δ (s, 1H), (d, J = 9.0 Hz, 1H), (m, 3H), 8.27 (dd, J = 22.3, 9.7 Hz, 2H), 8.02 (d, J = 8.6 Hz, 2H), 7.85 (t, J = 7.8 Hz, 1H), 7.73 (d, J = 8.2 Hz, 1H), 7.56 (t, J = 6.7 Hz, 3H), 7.11 (d, J = 8.8 Hz, 1H), 6.91 (t, J = 7.6 Hz, 1H). 13 C NMR (100 MHz, pyridine) δ 199.8, 178.9, 165.3, 163.4, 154.4, 143.1, 138.4, 137.1, 136.5, 135.3, 133.2, 133.0, 131.2, 129.6, 129.2, 127.1, 126.7, 126.3, 126.2, 125.4, 124.7, 124.0, 123.8, 123.2, 119.0, 118.9, 118.7, 118.2, ppm. HRMS calcd for C 29 H 16 N 2 O 6 M + : , found: references (1) Anh-Thu Dang, David O. Miller, Louise N. Dawe, and Graham J. Bodwell, Org.Lett. 2008, 10, 233. (2) V. A. Tuskaev, É. T. Oganesyan, and S. Kh. Mutsueva, Pharm. Chem. J. 2002, 36, 309. S11

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66 4. X-ray crystal structures of 3e X-ray crystal structure of 3e. Ellipsoid probability: 50%. S66