高等学校化学学报 ›› 2020, Vol. 41 ›› Issue (11): 2457.doi: 10.7503/cjcu20200340
收稿日期:
2020-06-10
出版日期:
2020-11-10
发布日期:
2020-11-06
通讯作者:
南江
E-mail:nanjiang@sust.edu.cn
基金资助:
NAN Jiang(), CHEN Pu, MA Yangmin
Received:
2020-06-10
Online:
2020-11-10
Published:
2020-11-06
Contact:
NAN Jiang
E-mail:nanjiang@sust.edu.cn
Supported by:
摘要:
利用廉价易得的2-乙烯基苯胺与重氮化合物在三氟乙酸催化下发生[5+1]环化反应, 以中等至良好的产率合成了24种2-芳基喹啉衍生物. 该方法无需金属催化剂, 官能团兼容性好, 反应成本低, 不仅拓展了重氮化合物参与的新型有机反应, 同时也为2-芳基取代喹啉的合成提供了高效、 经济且简洁的新方法.
中图分类号:
TrendMD:
南江, 陈璞, 马养民. 酸促进2-乙烯基苯胺与重氮的[5+1]环化合成2-芳基喹啉. 高等学校化学学报, 2020, 41(11): 2457.
NAN Jiang, CHEN Pu, MA Yangmin. Acid-promoted [5+1] Annulation of 2-Vinylanilines with Diazo Compounds to 2-Arylquinolines. Chem. J. Chinese Universities, 2020, 41(11): 2457.
Compd. | HRMS, m/z[M+H]+(calcd.) | Compd. | HRMS, m/z[M+H]+(calcd.) |
---|---|---|---|
1a | 196.1131(196.1126) | 1n | 274.0223(274.0231) |
1b | 210.1280(210.1283) | 1o | 280.0941(280.0949) |
1c | 230.0728(230.0737) | 1p | 268.1337(268.1338) |
1d | 246.1288(246.1283) | 1q | 226.1228(226.1232) |
1e | 202.0687(202.0690) | 2a | 219.0765(219.0770) |
1f | 134.0966(134.0970) | 2b | 249.0872(249.0875) |
1g | 210.1277(210.1283) | 2c | 296.9871(296.9875) |
1h | 188.1430(188.1439) | 2d | 225.0331(225.0334) |
1i | 210.1277(210.1283) | 2e | 209.0560(209.0562) |
1j | 226.1225(226.1232) | 2f | 269.0919(269.0926) |
1k | 242.1000(242.1003) | 2g | 157.0609(157.0613) |
1l | 272.1431(272.1439) | 2h | 143.0455(143.0457) |
1m | 214.1026(214.1032) |
Table 1 HRMS data of compounds 1a—1q and 2a—2h
Compd. | HRMS, m/z[M+H]+(calcd.) | Compd. | HRMS, m/z[M+H]+(calcd.) |
---|---|---|---|
1a | 196.1131(196.1126) | 1n | 274.0223(274.0231) |
1b | 210.1280(210.1283) | 1o | 280.0941(280.0949) |
1c | 230.0728(230.0737) | 1p | 268.1337(268.1338) |
1d | 246.1288(246.1283) | 1q | 226.1228(226.1232) |
1e | 202.0687(202.0690) | 2a | 219.0765(219.0770) |
1f | 134.0966(134.0970) | 2b | 249.0872(249.0875) |
1g | 210.1277(210.1283) | 2c | 296.9871(296.9875) |
1h | 188.1430(188.1439) | 2d | 225.0331(225.0334) |
1i | 210.1277(210.1283) | 2e | 209.0560(209.0562) |
1j | 226.1225(226.1232) | 2f | 269.0919(269.0926) |
1k | 242.1000(242.1003) | 2g | 157.0609(157.0613) |
1l | 272.1431(272.1439) | 2h | 143.0455(143.0457) |
1m | 214.1026(214.1032) |
Compd. | Appearance | Yield(%) | m. p./℃ | HRMS, m/z[M+H]+(calcd.) |
---|---|---|---|---|
3a | Yellow solid | 78 | 106—108(109—111[ | 282.1280(282.1283) |
3b | Yellow oil | 76 | 296.1431(296.1439) | |
3c | Yellow oil | 75 | 316.0890(316.0893) | |
3d | Yellow solid | 69 | 130—132 | 332.1443(332.1439) |
3e | Yellow oil | 47 | 288.0854(288.0847) | |
3f | Yellow oil | 57 | 220.1131(220.1126) | |
3g | Yellow solid | 63 | 145—147 | 296.1433(296.1439) |
3h | Yellow solid | 54 | 98—99 | 274.1595(274.1596) |
3i | Yellow solid | 74 | 132—134(125—127[ | 296.1440(296.1439) |
3j | Yellow solid | 65 | 115—117(116—119[ | 312.1380(312.1388) |
3k | Yellow solid | 47 | 142—144 | 328.1153(328.1160) |
3l | Yellow solid | 63 | 169—171(171—172[ | 358.1590(358.1596) |
3m | Pale yellow solid | 73 | 108—110 | 300.1185(300.1189) |
3n | Pale yellow solid | 77 | 156—158(154—155[ | 360.0381(360.0388) |
3o | White solid | 71 | 142—144 | 366.1105(366.1106) |
3p | Pale yellow solid | 40 | 143—145 | 354.1489(354.1494) |
3q | Yellow solid | 42 | 128—130(122—124[ | 312.1384(312.1388) |
3r | Yellow solid | 65 | 94—96 | 312.1384(312.1388) |
3s | Yellow solid | 76 | 133—135 | 360.0387(360.0388) |
3t | Yellow solid | 72 | 80—82(85—87[ | 288.0852(288.0847) |
3u | Brown solid | 67 | 101—103(100—102[ | 272.1070(272.1075) |
3v | Yellow solid | 67 | 126—128 | 332.1433(332.1439) |
3w | Yellow solid | 59 | 98—99(98—99[ | 220.1120(220.1126) |
3x | Pale yellow solid | 63 | 61—63(62—63[ | 206.0973(206.0970) |
Table 2 Appearance, yields, melting points(m. p.) and HRMS data of compounds 3a—3x
Compd. | Appearance | Yield(%) | m. p./℃ | HRMS, m/z[M+H]+(calcd.) |
---|---|---|---|---|
3a | Yellow solid | 78 | 106—108(109—111[ | 282.1280(282.1283) |
3b | Yellow oil | 76 | 296.1431(296.1439) | |
3c | Yellow oil | 75 | 316.0890(316.0893) | |
3d | Yellow solid | 69 | 130—132 | 332.1443(332.1439) |
3e | Yellow oil | 47 | 288.0854(288.0847) | |
3f | Yellow oil | 57 | 220.1131(220.1126) | |
3g | Yellow solid | 63 | 145—147 | 296.1433(296.1439) |
3h | Yellow solid | 54 | 98—99 | 274.1595(274.1596) |
3i | Yellow solid | 74 | 132—134(125—127[ | 296.1440(296.1439) |
3j | Yellow solid | 65 | 115—117(116—119[ | 312.1380(312.1388) |
3k | Yellow solid | 47 | 142—144 | 328.1153(328.1160) |
3l | Yellow solid | 63 | 169—171(171—172[ | 358.1590(358.1596) |
3m | Pale yellow solid | 73 | 108—110 | 300.1185(300.1189) |
3n | Pale yellow solid | 77 | 156—158(154—155[ | 360.0381(360.0388) |
3o | White solid | 71 | 142—144 | 366.1105(366.1106) |
3p | Pale yellow solid | 40 | 143—145 | 354.1489(354.1494) |
3q | Yellow solid | 42 | 128—130(122—124[ | 312.1384(312.1388) |
3r | Yellow solid | 65 | 94—96 | 312.1384(312.1388) |
3s | Yellow solid | 76 | 133—135 | 360.0387(360.0388) |
3t | Yellow solid | 72 | 80—82(85—87[ | 288.0852(288.0847) |
3u | Brown solid | 67 | 101—103(100—102[ | 272.1070(272.1075) |
3v | Yellow solid | 67 | 126—128 | 332.1433(332.1439) |
3w | Yellow solid | 59 | 98—99(98—99[ | 220.1120(220.1126) |
3x | Pale yellow solid | 63 | 61—63(62—63[ | 206.0973(206.0970) |
Compd. | 1H NMR(400 MHz, CDCl3), δ | 13C NMR(100 MHz, CDCl3), δ |
---|---|---|
3a | 8.27(d, J=8.4 Hz, 1H), 8.21(d, J=6.8 Hz, 2H), 7.92(d, J=8.4 Hz, 1H), 7.84(s, 1H), 7.75(t, J=7.2 Hz, 1H), 7.61—7.52(m, 7H), 7.52—7.45(m, 2H) | 156.8, 149.1, 148.7, 139.6, 138.3, 130.1, 129.5, 129.3, 128.8, 128.5, 128.4, 127.5, 126.3, 125.7, 125.6, 119.3 |
3b | 8.24(d, J=8.5 Hz, 1H), 8.19(d, J=7.1 Hz, 2H), 7.91(d, J=8.4 Hz, 1H), 7.81(s, 1H), 7.72(t, J=7.6 Hz, 1H), 7.52(t, J=7.3 Hz, 2H), 7.49—7.40(m, 3H), 7.39—7.29(m, 3H), 2.46(s, 3H) | 156.8, 149.3, 148.8, 139.7, 138.3, 130.2, 130.1, 129.4, 129.3, 129.1, 128.8, 128.4, 127.6, 126.6, 126.2, 125.8, 125.7, 119.3, 21.5 |
3c | 8.24(d, J=8.4 Hz, 1H), 8.17(d, J=7.2 Hz, 2H), 7.83(d, J=8.0 Hz, 1H), 7.77(s, 1H), 7.73(t, J=6.8 Hz, 1H), 7.56—7.43(m, 8H) | 156.8, 148.7, 147.8, 139.4, 136.7, 134.5, 130.8, 130.2, 129.6, 129.4, 128.8, 127.5, 126.5, 125.4, 125.2, 119.2 |
3d | 8.28(d, J=8.4 Hz, 1H), 8.21(d, J=7.2 Hz, 2H), 7.98(dd, J=14.5, 8.2 Hz, 2H), 7.92(s, 1H), 7.71(t, J=8.4 Hz, 1H), 7.62(t, J=7.2 Hz, 1H), 7.55—7.49(m, 4H), 7.49—7.40(m, 3H), 7.33(t, J=8.2 Hz, 2H) | 156.8, 148.5, 148.0, 139.5, 136.0, 133.5, 132.0, 123.0, 129.6, 129.4, 128.8, 128.3, 127.6, 127.4, 127.0, 126.5, 126.3, 126.2, 126.1, 126.0, 125.3, 120.5 |
3e | 8.25(dd, J=14.3, 8.7 Hz, 2H), 8.18(d, J=7.2 Hz, 2H), 7.92(s, 1H), 7.78(t, J=7.2 Hz, 1H), 7.57—7.50(m, 4H), 7.48(d, J=7.2 Hz, 1H), 7.43(d, J=3.6 Hz, 1H), 7.24(t, J=5.1 Hz, 1H) | 156.9, 149.0, 141.5, 139.4, 139.2, 130.2, 129.7, 129.4, 128.8, 128.5, 127.8, 127.5, 127.1, 126.7, 125.4, 125.3, 119.8 |
3f | 8.20—8.11(m, 3H), 7.98(d, J=8.4 Hz, 1H), 7.76—7.66(m, 2H), 7.57—7.42(m, 4H), 2.75(s, 3H) | 157.0, 148.1, 144.7, 139.8, 130.2, 129.3, 129.1, 128.7, 127.5, 127.2, 126.0, 123.6, 119.7, 19.0 |
3g | 8.23(d, J=12.0 Hz, 1H), 7.73—7.64(m, 3H), 7.62—7.39(m, 8H), 7.39—7.33(m, 2H), 2.21(s, 3H) | 160.9, 147.8, 146.3, 141.6, 137.8, 129.5, 129.4, 129.0, 128.7, 128.6, 128.4, 128.1, 127.9, 127.1, 126.8, 126.3, 126.0, 18.7 |
3h | 8.16(t, J=8.4 Hz, 2H), 7.68(t, J=8.4 Hz, 1H), 7.61—7.38(m, 6H), 3.45—3.27(m, 2H), 3.09—2.92(m, 2H), 1.98—1.93(m, 2H), 1.82(q, J=5.8 Hz, 2H), 1.68(q, J=5.6 Hz, 2H) | 159.9, 149.4, 146.4, 141.9, 134.2, 130.3, 129.0, 128.3, 128.2, 127.8, 126.2, 126.1, 123.0, 32.0, 30.8, 28.1, 27.0, 26.1 |
3i | 8.24(d, J=8.5 Hz, 1H), 8.19(d, J=7.1 Hz, 2H), 7.91(d, J=8.4 Hz, 1H), 7.81(s, 1H), 7.72(t, J=7.6 Hz, 1H), 7.52(t, J=7.3 Hz, 2H), 7.49—7.40(m, 3H), 7.39—7.29(m, 3H), 2.46(s, 3H) | 156.8, 149.3, 148.8, 139.7, 138.3, 130.2, 130.1, 129.4, 129.3, 129.1, 128.8, 128.4, 127.6, 126.6, 126.2, 125.8, 125.7, 119.3, 21.5 |
Compd. | 1H NMR(400 MHz, CDCl3), δ | 13C NMR(100 MHz, CDCl3), δ |
3j | 8.19—8.12(m, 3H), 7.77(s, 1H), 7.61—7.53(m, 4H), 7.53—7.47(m, 3H), 7.46—7.35(m, 2H), 7.19(d, J=2.8 Hz, 1H), 3.79(s, 3H) | 157.7, 154.6, 147.7, 144.9, 139.7, 138.7, 131.6, 129.3, 128.9, 128.8, 128.7, 128.3, 127.3, 126.6, 121.8, 119.6, 103.6, 55.4 |
3k | 8.25—8.07(m, 3H), 7.79(s, 1H), 7.66(d, J=2.1 Hz, 1H), 7.61(dd, J=8.8, 2.2 Hz, 1H), 7.58—7.41(m, 8H), 2.46(s, 3H) | 156.1, 147.9, 147.1, 139.5, 138.3, 137.1, 130.4, 129.5, 129.3, 129.0, 128.9, 128.7, 128.5, 127.5, 126.2, 121.1, 119.9, 15.8 |
3l | 8.37(d, J=8.7 Hz, 1H), 8.27(d, J=6.8 Hz, 2H), 8.16(d, J=2.0 Hz, 1H), 8.05(dd, J=8.7, 2.1 Hz, 1H), 7.90(s, 1H), 7.70—7.64(m, 4H), 7.64—7.55(m, 5H), 7.55—7.46(m, 3H), 7.43—7.37(m, 1H) | 156.7, 149.3, 148.2, 140.6, 139.5, 139.0, 138.3, 130.5, 129.5, 129.3, 129.2, 128.8, 128.7, 128.4, 127.5, 127.4, 125.9, 123.3, 119.7 |
3m | 8.23(dd, J=9.1, 5.6 Hz, 1H), 8.17(d, J=7.2 Hz, 2H), 7.83(s, 1H), 7.58—7.44(m, 10H) | 159.3(d, J=245.7 Hz), 156.3(d, J=2.7 Hz), 148.6(d, J=5.5 Hz), 145.9, 139.3, 137.9, 132.5(d, J=9 Hz), 129.4, 129.3, 128.9, 128.8, 128.6, 127.4, 126.4(d, J=9.4 Hz), 119.8, 119.5(d, J=25.5 Hz), 108.9(d, J=22.9 Hz) |
3n | 8.21—8.14(m, 2H), 8.09(d, J=9.0 Hz, 1H), 8.03(d, J=2.2 Hz, 1H), 7.82(s, 1H), 7.78(dd, J=8.9, 2.2 Hz, 1H), 7.58—7.46(m, 8H) | 157.1, 148.3, 147.3, 139.1, 137.6, 132.9, 131.8, 129.6, 129.4, 128.8, 128.7, 127.7, 127.5, 126.9, 120.4, 120.0 |
3o | 8.31(d, J=9.2 Hz, 1H), 8.27—8.18(m, 2H), 7.91(s, 1H), 7.82—7.74(m, 1H), 7.67—7.47(m, 9H) | 157.4, 149.2, 147.2, 147.0, 139.2, 137.6, 132.3, 129.7, 129.4, 128.9, 128.8, 127.6, 126.1, 123.5, 120.1(q, J=256.1 Hz), 116.5 |
3p | 8.68(d, J=1.9 Hz, 1H), 8.36—8.16(m, 4H), 7.88(s, 1H), 7.65—7.46(m, 8H), 4.40(q, J=7.1 Hz, 2H), 1.39(t, J=7.1 Hz, 3H) | 166.4, 158.7, 150.7, 150.5, 139.1, 137.7, 130.3, 129.8, 129.6, 129.0, 128.9, 128.8, 128.1, 127.7, 125.0, 119.9, 61.2, 14.3 |
3q | 8.21(d, J=6.8 Hz, 2H), 7.84(s, 1H), 7.57—7.42(m, 9H), 7.37(t, J=7.6 Hz, 1H), 7.07(d, J=7.7 Hz, 1H), 4.11(s, 3H) | 155.7, 155.6, 149.1, 140.7, 139.7, 138.7, 129.5, 129.1, 128.7, 128.4, 128.3, 127.6, 126.8, 126.2, 119.8, 117.4, 107.9, 56.2 |
3r | 8.25(d, J=8.6 Hz, 1H), 8.20(d, J=8.8 Hz, 2H), 7.91(d, J=8.4 Hz, 1H), 7.81(s, 1H), 7.74(t, J=7.2 Hz, 1H), 7.61—7.53(m, 5H), 7.47(t, J=7.2 Hz, 1H), 7.07(d, J=8.8 Hz, 2H), 3.91(s, 3H) | 160.8, 156.4, 148.9, 148.7, 138.5, 132.2, 129.9, 129.5 129.4, 128.9, 128.5, 128.3, 125.9, 125.6, 125.5, 118.8, 114.2, 55.4 |
3s | 8.26(d, J=8.4 Hz, 1H), 8.11(d, J=8.4 Hz, 2H), 7.93(d, J=8.4 Hz, 1H), 7.80(s, 1H), 7.76(t, J=7.2 Hz, 1H), 7.67(d, J=8.8 Hz, 2H), 7.61—7.54(m, 5H), 7.51(t, J=8.3 Hz, 1H) | 155.5, 149.4, 148.7, 138.4, 138.2, 131.9, 130.0, 129.7, 129.5, 129.0, 128.6, 128.5, 126.5, 125.8, 125.6, 123.9, 118.8 |
3t | 8.19(d, J=8.4 Hz, 1H), 7.87(d, J=8.4 Hz, 1H), 7.78—7.75(m, 2H), 7.73(t, J=7.2 Hz, 1H), 7.60—7.52(m, 5H), 7.50(d, J= 5.0 Hz, 1H), 7.46(t, J=6.8 Hz, 1H), 7.18(dd, J=5.1, 3.7 Hz, 1H) | 151.8, 149.0, 148.6, 145.3, 138.1, 129.6, 129.5, 128.6, 128.5, 128.4, 128.0, 126.1, 125.8, 125.6, 117.9 |
3u | 8.23(d, J=8.4 Hz, 1H), 7.88(d, J=8.4 Hz, 1H), 7.79(s, 1H), 7.73(t, J=8.4 Hz, 1H), 7.65(dd, J=1.8, 0.8 Hz, 1H), 7.60—7.51(m, 5H), 7.47(t, J=7.2 Hz, 1H), 7.26(d, J=3.4 Hz, 1H), 6.62(dd, J=3.4, 1.8 Hz, 1H) | 153.7, 149.1, 148.6, 148.5, 144.1, 138.1, 129.7, 129.5, 128.6, 128.4, 126.2, 125.8, 125.7, 117.7, 112.2, 110.2 |
3v | 8.69(s, 1H), 8.46(d, J=8.6 Hz, 1H), 8.34(d, J=8.4 Hz, 1H), 8.07—8.00(m, 3H), 8.00—7.90(m, 2H), 7.79(t, J=7.2 Hz, 1H), 7.69—7.50(m, 8H) | 156.6, 149.2, 148.9, 138.4, 136.9, 133.9, 133.5, 130.1, 129.6, 128.8, 128.6, 128.5, 128.4, 127.7, 127.1, 126.7, 126.4, 126.3, 125.8, 125.7, 125.0, 119.4 |
3w | 8.11(d, J=8.4 Hz, 1H), 7.88(d, J=8.4 Hz, 1H), 7.71(t, J=8.0 Hz, 1H), 7.63—7.49(m, 5H), 7.45(t, J=7.2 Hz, 1H), 7.26(s, 1H), 2.80(s, 3H) | 158.5, 148.5, 148.4, 138.1, 129.5, 129.3, 129.0, 128.5, 128.3, 125.7, 125.6, 125.0, 122.2, 25.3 |
3x | 8.97(d, J=4.4 Hz, 1H), 8.21(d, J=8.4 Hz, 1H), 7.95(d, J=8.5 Hz, 1H), 7.75(t, J=6.8 Hz, 1H), 7.61—7.46(m, 6H), 7.36(d, J=4.4 Hz, 1H) | 149.9, 148.6, 148.4, 137.9, 129.8, 129.5, 129.3, 128.5, 128.4, 126.7, 126.6, 125.8, 121.3 |
Table 3 1H NMR and 13C NMR data of compounds 3a—3x
Compd. | 1H NMR(400 MHz, CDCl3), δ | 13C NMR(100 MHz, CDCl3), δ |
---|---|---|
3a | 8.27(d, J=8.4 Hz, 1H), 8.21(d, J=6.8 Hz, 2H), 7.92(d, J=8.4 Hz, 1H), 7.84(s, 1H), 7.75(t, J=7.2 Hz, 1H), 7.61—7.52(m, 7H), 7.52—7.45(m, 2H) | 156.8, 149.1, 148.7, 139.6, 138.3, 130.1, 129.5, 129.3, 128.8, 128.5, 128.4, 127.5, 126.3, 125.7, 125.6, 119.3 |
3b | 8.24(d, J=8.5 Hz, 1H), 8.19(d, J=7.1 Hz, 2H), 7.91(d, J=8.4 Hz, 1H), 7.81(s, 1H), 7.72(t, J=7.6 Hz, 1H), 7.52(t, J=7.3 Hz, 2H), 7.49—7.40(m, 3H), 7.39—7.29(m, 3H), 2.46(s, 3H) | 156.8, 149.3, 148.8, 139.7, 138.3, 130.2, 130.1, 129.4, 129.3, 129.1, 128.8, 128.4, 127.6, 126.6, 126.2, 125.8, 125.7, 119.3, 21.5 |
3c | 8.24(d, J=8.4 Hz, 1H), 8.17(d, J=7.2 Hz, 2H), 7.83(d, J=8.0 Hz, 1H), 7.77(s, 1H), 7.73(t, J=6.8 Hz, 1H), 7.56—7.43(m, 8H) | 156.8, 148.7, 147.8, 139.4, 136.7, 134.5, 130.8, 130.2, 129.6, 129.4, 128.8, 127.5, 126.5, 125.4, 125.2, 119.2 |
3d | 8.28(d, J=8.4 Hz, 1H), 8.21(d, J=7.2 Hz, 2H), 7.98(dd, J=14.5, 8.2 Hz, 2H), 7.92(s, 1H), 7.71(t, J=8.4 Hz, 1H), 7.62(t, J=7.2 Hz, 1H), 7.55—7.49(m, 4H), 7.49—7.40(m, 3H), 7.33(t, J=8.2 Hz, 2H) | 156.8, 148.5, 148.0, 139.5, 136.0, 133.5, 132.0, 123.0, 129.6, 129.4, 128.8, 128.3, 127.6, 127.4, 127.0, 126.5, 126.3, 126.2, 126.1, 126.0, 125.3, 120.5 |
3e | 8.25(dd, J=14.3, 8.7 Hz, 2H), 8.18(d, J=7.2 Hz, 2H), 7.92(s, 1H), 7.78(t, J=7.2 Hz, 1H), 7.57—7.50(m, 4H), 7.48(d, J=7.2 Hz, 1H), 7.43(d, J=3.6 Hz, 1H), 7.24(t, J=5.1 Hz, 1H) | 156.9, 149.0, 141.5, 139.4, 139.2, 130.2, 129.7, 129.4, 128.8, 128.5, 127.8, 127.5, 127.1, 126.7, 125.4, 125.3, 119.8 |
3f | 8.20—8.11(m, 3H), 7.98(d, J=8.4 Hz, 1H), 7.76—7.66(m, 2H), 7.57—7.42(m, 4H), 2.75(s, 3H) | 157.0, 148.1, 144.7, 139.8, 130.2, 129.3, 129.1, 128.7, 127.5, 127.2, 126.0, 123.6, 119.7, 19.0 |
3g | 8.23(d, J=12.0 Hz, 1H), 7.73—7.64(m, 3H), 7.62—7.39(m, 8H), 7.39—7.33(m, 2H), 2.21(s, 3H) | 160.9, 147.8, 146.3, 141.6, 137.8, 129.5, 129.4, 129.0, 128.7, 128.6, 128.4, 128.1, 127.9, 127.1, 126.8, 126.3, 126.0, 18.7 |
3h | 8.16(t, J=8.4 Hz, 2H), 7.68(t, J=8.4 Hz, 1H), 7.61—7.38(m, 6H), 3.45—3.27(m, 2H), 3.09—2.92(m, 2H), 1.98—1.93(m, 2H), 1.82(q, J=5.8 Hz, 2H), 1.68(q, J=5.6 Hz, 2H) | 159.9, 149.4, 146.4, 141.9, 134.2, 130.3, 129.0, 128.3, 128.2, 127.8, 126.2, 126.1, 123.0, 32.0, 30.8, 28.1, 27.0, 26.1 |
3i | 8.24(d, J=8.5 Hz, 1H), 8.19(d, J=7.1 Hz, 2H), 7.91(d, J=8.4 Hz, 1H), 7.81(s, 1H), 7.72(t, J=7.6 Hz, 1H), 7.52(t, J=7.3 Hz, 2H), 7.49—7.40(m, 3H), 7.39—7.29(m, 3H), 2.46(s, 3H) | 156.8, 149.3, 148.8, 139.7, 138.3, 130.2, 130.1, 129.4, 129.3, 129.1, 128.8, 128.4, 127.6, 126.6, 126.2, 125.8, 125.7, 119.3, 21.5 |
Compd. | 1H NMR(400 MHz, CDCl3), δ | 13C NMR(100 MHz, CDCl3), δ |
3j | 8.19—8.12(m, 3H), 7.77(s, 1H), 7.61—7.53(m, 4H), 7.53—7.47(m, 3H), 7.46—7.35(m, 2H), 7.19(d, J=2.8 Hz, 1H), 3.79(s, 3H) | 157.7, 154.6, 147.7, 144.9, 139.7, 138.7, 131.6, 129.3, 128.9, 128.8, 128.7, 128.3, 127.3, 126.6, 121.8, 119.6, 103.6, 55.4 |
3k | 8.25—8.07(m, 3H), 7.79(s, 1H), 7.66(d, J=2.1 Hz, 1H), 7.61(dd, J=8.8, 2.2 Hz, 1H), 7.58—7.41(m, 8H), 2.46(s, 3H) | 156.1, 147.9, 147.1, 139.5, 138.3, 137.1, 130.4, 129.5, 129.3, 129.0, 128.9, 128.7, 128.5, 127.5, 126.2, 121.1, 119.9, 15.8 |
3l | 8.37(d, J=8.7 Hz, 1H), 8.27(d, J=6.8 Hz, 2H), 8.16(d, J=2.0 Hz, 1H), 8.05(dd, J=8.7, 2.1 Hz, 1H), 7.90(s, 1H), 7.70—7.64(m, 4H), 7.64—7.55(m, 5H), 7.55—7.46(m, 3H), 7.43—7.37(m, 1H) | 156.7, 149.3, 148.2, 140.6, 139.5, 139.0, 138.3, 130.5, 129.5, 129.3, 129.2, 128.8, 128.7, 128.4, 127.5, 127.4, 125.9, 123.3, 119.7 |
3m | 8.23(dd, J=9.1, 5.6 Hz, 1H), 8.17(d, J=7.2 Hz, 2H), 7.83(s, 1H), 7.58—7.44(m, 10H) | 159.3(d, J=245.7 Hz), 156.3(d, J=2.7 Hz), 148.6(d, J=5.5 Hz), 145.9, 139.3, 137.9, 132.5(d, J=9 Hz), 129.4, 129.3, 128.9, 128.8, 128.6, 127.4, 126.4(d, J=9.4 Hz), 119.8, 119.5(d, J=25.5 Hz), 108.9(d, J=22.9 Hz) |
3n | 8.21—8.14(m, 2H), 8.09(d, J=9.0 Hz, 1H), 8.03(d, J=2.2 Hz, 1H), 7.82(s, 1H), 7.78(dd, J=8.9, 2.2 Hz, 1H), 7.58—7.46(m, 8H) | 157.1, 148.3, 147.3, 139.1, 137.6, 132.9, 131.8, 129.6, 129.4, 128.8, 128.7, 127.7, 127.5, 126.9, 120.4, 120.0 |
3o | 8.31(d, J=9.2 Hz, 1H), 8.27—8.18(m, 2H), 7.91(s, 1H), 7.82—7.74(m, 1H), 7.67—7.47(m, 9H) | 157.4, 149.2, 147.2, 147.0, 139.2, 137.6, 132.3, 129.7, 129.4, 128.9, 128.8, 127.6, 126.1, 123.5, 120.1(q, J=256.1 Hz), 116.5 |
3p | 8.68(d, J=1.9 Hz, 1H), 8.36—8.16(m, 4H), 7.88(s, 1H), 7.65—7.46(m, 8H), 4.40(q, J=7.1 Hz, 2H), 1.39(t, J=7.1 Hz, 3H) | 166.4, 158.7, 150.7, 150.5, 139.1, 137.7, 130.3, 129.8, 129.6, 129.0, 128.9, 128.8, 128.1, 127.7, 125.0, 119.9, 61.2, 14.3 |
3q | 8.21(d, J=6.8 Hz, 2H), 7.84(s, 1H), 7.57—7.42(m, 9H), 7.37(t, J=7.6 Hz, 1H), 7.07(d, J=7.7 Hz, 1H), 4.11(s, 3H) | 155.7, 155.6, 149.1, 140.7, 139.7, 138.7, 129.5, 129.1, 128.7, 128.4, 128.3, 127.6, 126.8, 126.2, 119.8, 117.4, 107.9, 56.2 |
3r | 8.25(d, J=8.6 Hz, 1H), 8.20(d, J=8.8 Hz, 2H), 7.91(d, J=8.4 Hz, 1H), 7.81(s, 1H), 7.74(t, J=7.2 Hz, 1H), 7.61—7.53(m, 5H), 7.47(t, J=7.2 Hz, 1H), 7.07(d, J=8.8 Hz, 2H), 3.91(s, 3H) | 160.8, 156.4, 148.9, 148.7, 138.5, 132.2, 129.9, 129.5 129.4, 128.9, 128.5, 128.3, 125.9, 125.6, 125.5, 118.8, 114.2, 55.4 |
3s | 8.26(d, J=8.4 Hz, 1H), 8.11(d, J=8.4 Hz, 2H), 7.93(d, J=8.4 Hz, 1H), 7.80(s, 1H), 7.76(t, J=7.2 Hz, 1H), 7.67(d, J=8.8 Hz, 2H), 7.61—7.54(m, 5H), 7.51(t, J=8.3 Hz, 1H) | 155.5, 149.4, 148.7, 138.4, 138.2, 131.9, 130.0, 129.7, 129.5, 129.0, 128.6, 128.5, 126.5, 125.8, 125.6, 123.9, 118.8 |
3t | 8.19(d, J=8.4 Hz, 1H), 7.87(d, J=8.4 Hz, 1H), 7.78—7.75(m, 2H), 7.73(t, J=7.2 Hz, 1H), 7.60—7.52(m, 5H), 7.50(d, J= 5.0 Hz, 1H), 7.46(t, J=6.8 Hz, 1H), 7.18(dd, J=5.1, 3.7 Hz, 1H) | 151.8, 149.0, 148.6, 145.3, 138.1, 129.6, 129.5, 128.6, 128.5, 128.4, 128.0, 126.1, 125.8, 125.6, 117.9 |
3u | 8.23(d, J=8.4 Hz, 1H), 7.88(d, J=8.4 Hz, 1H), 7.79(s, 1H), 7.73(t, J=8.4 Hz, 1H), 7.65(dd, J=1.8, 0.8 Hz, 1H), 7.60—7.51(m, 5H), 7.47(t, J=7.2 Hz, 1H), 7.26(d, J=3.4 Hz, 1H), 6.62(dd, J=3.4, 1.8 Hz, 1H) | 153.7, 149.1, 148.6, 148.5, 144.1, 138.1, 129.7, 129.5, 128.6, 128.4, 126.2, 125.8, 125.7, 117.7, 112.2, 110.2 |
3v | 8.69(s, 1H), 8.46(d, J=8.6 Hz, 1H), 8.34(d, J=8.4 Hz, 1H), 8.07—8.00(m, 3H), 8.00—7.90(m, 2H), 7.79(t, J=7.2 Hz, 1H), 7.69—7.50(m, 8H) | 156.6, 149.2, 148.9, 138.4, 136.9, 133.9, 133.5, 130.1, 129.6, 128.8, 128.6, 128.5, 128.4, 127.7, 127.1, 126.7, 126.4, 126.3, 125.8, 125.7, 125.0, 119.4 |
3w | 8.11(d, J=8.4 Hz, 1H), 7.88(d, J=8.4 Hz, 1H), 7.71(t, J=8.0 Hz, 1H), 7.63—7.49(m, 5H), 7.45(t, J=7.2 Hz, 1H), 7.26(s, 1H), 2.80(s, 3H) | 158.5, 148.5, 148.4, 138.1, 129.5, 129.3, 129.0, 128.5, 128.3, 125.7, 125.6, 125.0, 122.2, 25.3 |
3x | 8.97(d, J=4.4 Hz, 1H), 8.21(d, J=8.4 Hz, 1H), 7.95(d, J=8.5 Hz, 1H), 7.75(t, J=6.8 Hz, 1H), 7.61—7.46(m, 6H), 7.36(d, J=4.4 Hz, 1H) | 149.9, 148.6, 148.4, 137.9, 129.8, 129.5, 129.3, 128.5, 128.4, 126.7, 126.6, 125.8, 121.3 |
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