Chemical Journal of Chinese Universities ›› 2020, Vol. 41 ›› Issue (11): 2457-2463.doi: 10.7503/cjcu20200340
• Organic Chemistry • Previous Articles Next Articles
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:
CLC Number:
NAN Jiang, CHEN Pu, MA Yangmin. Acid-promoted [5+1] Annulation of 2-Vinylanilines with Diazo Compounds to 2-Arylquinolines[J]. Chemical Journal of Chinese Universities, 2020, 41(11): 2457-2463.
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. | 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) |
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 |
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 |
1 | McCauley E. P., Smith G. C., Crews P., J. Nat. Prod., 2020, 83(1),174—178 |
2 | Michael J. P., Nat. Prod. Rep., 2007, 24(1), 223—246 |
3 | Nainwal L. M., Tasneem S., Akhtar W., Verma G., Khan M. F., Parvez S., Shaquiquzzaman M., Akhter M., Alam M. M., Eur. J. Org. Chem., 2019, 164, 121—170 |
4 | Li Y. J., Wang E. S., Shao X. W., Zhang X. M., Niu S. X., Yang L. J., Wu Y., Chem. J. Chinese Universities, 2019, 40(12), 2502—2511(李艳杰, 王恩思, 邵晓玮, 张兴民, 牛生秀, 杨丽娟, 武毅. 高等学校化学学报, 2019, 40(12), 2502—2511) |
5 | Dong Q. C., Zhang G. H., Zhang W. B., Liu J., Chem. J. Chinese Universities, 2019, 40(10), 2195—2204(董秋辰, 张光华, 张万斌, 刘晶. 高等学校化学学报, 2019, 40(10), 2195—2204) |
6 | Xu P. F., Zhang Z. H., Hui X. P., Zhang Z. Y., Zheng R. L., J. Chin. Chem. Soc., 2004, 51(2), 315—319 |
7 | Painuly D., Mullemwar S. Y., Rabanal M. E., Singhal R., Nagpure I. M., Appl. Phys. A, 2019, 125(2), 1—10 |
8 | Xu W. J., Liu S. J., Ma T. C., Zhao Q., Pertegas A., Tordera D., Bolink H. J., Ye S. H., Liu X. M., Sun S., Huang W., J. Mater. Chem., 2011, 21(36), 13999—14007 |
9 | Tago T., Furumoto S., Okamura N., Harada R., Ishikawa Y., Arai H., Yanai K., Iwata R., Kudo Y., J. Label Compd. Radiopharm, 2014, 57(1), 18—24 |
10 | Ronellenfitsch M., Wadepohl H., Enders M., Organometallics, 2014, 33(20), 5758—5766 |
11 | Madapa S., Tusi Z., Batra S., Curr. Org. Chem., 2008, 12(13),1116—1183 |
12 | Born J. L., J. Org. Chem., 1972, 37(24), 3952—3953 |
13 | Matsugi M., Tabusa F., Minamikawa J. I., Tetrahedron Lett., 2000, 41(44), 8523—8525 |
14 | Marco⁃Contelles J., Perez⁃Mayoral E., Samadi A., Carreiras M. C., Soriano E., Chem. Rev., 2009, 109(6),2652—2671 |
15 | Bryson T. A., Gibson J. M., Stewart J. J., Voegtle H., Tiwari A., Dawson J. H., Marley W., Harmon B., Green Chem., 2003, 5(2), 177—180 |
16 | Chen X. Z., Qiu S. X., Wang S. S., Wang H. F., Zhai H. B., Org. Biomol. Chem., 2017, 15(30), 6349—6352 |
17 | Lee S. Y., Jeon J., Cheon C. H., J. Org. Chem., 2018, 83(9), 5177—5186 |
18 | Lee S. Y., Cheon C. H., J. Org. Chem., 2018, 83(21), 13036—13044 |
19 | Zhu J. W., Hu W. M., Sun S., Yu J. T., Cheng J., Adv. Synth. Catal., 2017, 359(21), 3725—3728 |
20 | Pang X. B., Wu M. Z., Ni J. X., Zhang F. M., Lan J. F., Chen B. H., Yan R. L., J. Org. Chem., 2017, 82(19), 10110—10120 |
21 | Reddy A. C. S., Anbarasan P., J. Catal., 2018, 363, 102—108 |
22 | Bohmann R. A., Schoebel J. H., Unoh Y., Miura M., Bolm C., Adv. Synth. Catal., 2019, 361(9), 2000—2003 |
23 | Shi Z., Koester D. C., Boultadakis⁃Arapinis M., Glorius F., J. Am. Chem. Soc., 2013, 135(33), 12204—12207 |
24 | Chen X. H., Zheng G. F., Song G. Y., Li X. W., Adv. Synth. Catal., 2018, 360(15), 2836—2842 |
25 | Guo S. J., Yuan K., Gu M., Lin A. J., Yao H. Q., Org. Lett., 2016, 18(20), 5236—5239 |
26 | Wu Y. Z., Sun P., Zhang K. F., Yang T., Yao H. Q., Lin A. J., J. Org. Chem., 2016, 81(5), 2166—2173 |
27 | Li X. G., Sun M., Jin Q., Liu K., Liu P. N., J. Org. Chem., 2016, 81(9), 3901—3910 |
28 | Xiao Y., Xiong H., Sun S., Yu J. T., Cheng J., Org. Biomol. Chem., 2018, 16(45), 8715—8718 |
29 | Tang Z. H., Mai S. Y., Zhou Y., Song Q. L., Org. Chem. Front., 2018, 5(17), 2583—2587 |
30 | Chen X., Hu X. W., Bai S. Y., Deng Y. F., Jiang H. F., Zeng W., Org. Lett., 2016, 18(2), 192—195 |
31 | Wang C., Ding Q. P., Zheng Q., Bao P., Peng Y. Y., Tetrahedron, 2018, 74(2), 348—353 |
32 | Guo S. H., Sun L. C., Li X. Z., Zhang X. Y., Fan X. S., Adv. Synth. Catal., 2020, 362(4), 913—926 |
33 | Chen P., Nan J., Hu Y., Ma Q., Ma Y. M., Org. Lett., 2019, 21(12), 4812—4815 |
34 | Nan J., Hu Y., Chen P., Ma Y. M., Org. Lett., 2019, 21(7), 1984—1988 |
35 | Huang Y. N., Li Y. L., Li J., Deng J., J. Org. Chem.,2016, 81(11), 4645—4653 |
36 | Li D. J., Zeng F. L., Org. Lett.,2017, 19(24), 6498—6501 |
37 | Wang J., Wang M. Y., Chen K. H., Zha S. K., Song C., Zhu J., Org. Lett.,2016, 18(5), 1178—1181 |
38 | Guo X., Han J. W., Liu Y. F., Qin M. D., Zhang X. G., Chen B. H., J. Org. Chem.,2017, 82(21), 11505—11511 |
39 | Tan W. W., Yoshikai N., Chem. Sci.,2015, 6(11), 6448—6455 |
40 | Liu Y., Li S. J., Chen X. L., Fan L. L., Li X. Y., Zhu S. S., Qu L. B., Yu B., Adv. Synth. Catal., 2020, 362(2), 688—694 |
41 | Leardini R., Nanni D., Pedulli G. F., Tundo A., Zanardi G., J. Chem. Soc., Perkin Trans. 1, Organic and Bio-Organic Chemistry, 1986, 9, 1591—1594 |
42 | Spallino R., Salimei G., Gazzetta Chimica Italiana, 1912, 42(I), 607—612 |
43 | Walker S. D., Barder T. E., Martinelli J. R., Buchwald S. L., Angew. Chem. Int. Ed., 2004, 43(14), 1871-1876 |
44 | Fisher T. J., Mattson A. E., Org. Lett., 2014, 16(20), 5316—5319 |
45 | Tan F., Liu X. H., Hao X. Y., Tang Y., Lin L. L., Feng X. M., ACS Catal., 2016, 6(10), 6930—6934 |
46 | Xie C. X., Feng L., Li W. L., Ma X. J., Ma X. K., Liu Y. H., Ma C., Org. Biomol. Chem., 2016, 14(36), 8529—8535 |
47 | Chowdhury D., Dana S., Mandal A., Baidya M., Chem. Commun., 2019, 55(79), 11908—11911 |
[1] | LIU Chang, ZHANG Pengfei, LI Pengfei. Asymmetric Organocatalytic Enantioselective [1+4]-Annulation of Morita-Baylis-Hillman Carbonates with Thiazolyl Enones for Assembling of Dihydrofurans Featuring Thiazole Skeleton [J]. Chemical Journal of Chinese Universities, 2020, 41(10): 2272-2278. |
[2] | CHEN Danyi, ZHANG Fumei, HE Dan, ZHANG Zimei, ZHONG Fen, WEN Simiaomiao, LIU Qixing, ZHOU Haifeng. Synthesis of Chiral Phenylbenzothiazole Methanol via Transfer Hydrogenation Catalyzed by Ruthenium Complexes† [J]. Chemical Journal of Chinese Universities, 2020, 41(10): 2264-2271. |
[3] | PAN Yixiao, LI Yanwen, HAN Jiahong, ZHAO Haoqiang, FENG Yu, DING Xiangyuan, XU Lijin, FAN Qinghua, SHI Qian. Synthesis of 1,2,3,4-Tetrahydroquinoxalines Through a One-pot Tandem Reaction Involving Cyclization and Hydrogenation of Imine and Amide Moieties [J]. Chemical Journal of Chinese Universities, 2020, 41(10): 2239-2255. |
[4] | MA Jinyu, LIU Shuanglei, ZHANG Zhenguo, JIN Junyang, JIA Zhenhua. B(C6F5)3-Catalyzed Synthesis of 3,3′-Bisindolylmethane Derivatives [J]. Chemical Journal of Chinese Universities, 2020, 41(10): 2225-2229. |
[5] | ZHANG Chenglu, SUN Yuedong, WANG Jing, HE Yu, ZHANG Yanpeng, ZHANG Lu, SONG Fulu. Synthesis and Application of Quinolinone Derivative Fluorescent Probe for High Selective Detection of Hg2+ [J]. Chemical Journal of Chinese Universities, 2020, 41(8): 1785-1791. |
[6] | REN Yushuang, GUO Yuanyuan, LIU Xueyi, SONG Jie, ZHANG Chuan. Platinum(Ⅳ) Prodrug-grafted Phosphorothioate DNA and Its Self-assembled Nanostructure for Targeted Drug Delivery [J]. Chemical Journal of Chinese Universities, 2020, 41(8): 1721-1730. |
[7] | ZHOU Chunni, ZHENG Ziang, PENG Wangming, WANG Hongbo, ZHANG Yumin, WANG Liang, XIAO Biao. Microwave Assisted Rhodium-catalyzed C—H Activation/cyclization of Diaryl Phosphoramides and Alkynes † [J]. Chemical Journal of Chinese Universities, 2020, 41(4): 726-734. |
[8] | LI Kangming, LI Yansai, YI Yangjie, XU Leitao, YE Jiao, OU Xiaoming, LI Jianming, HU Aixi. Design, Synthesis and Biological Activity of 5-Pyrazole Carboxamides † [J]. Chemical Journal of Chinese Universities, 2020, 41(4): 716-725. |
[9] | TIAN Xia,YANG Fuqun,YUAN Wei,ZHAO Lei,YAO Lei,ZHEN Xiaoli,HAN Jianrong,LIU Shouxin. Synthesis, Structure and Recognition Properties of Macrocyclic Crown Ethers with Oxadiazole [J]. Chemical Journal of Chinese Universities, 2020, 41(3): 490-497. |
[10] | DAI Jianan,YANG Ziqi,WEI Zhonglin,CAO Jungang,LIANG Dapeng,DUAN Haifeng,LIN Yingjie. Synthesis of 6-Aminoformyl-substituted Phenanthridines Promoted by TBAC/TBHP System† [J]. Chemical Journal of Chinese Universities, 2019, 40(4): 712-718. |
[11] | Yanjie LI,Ensi WANG,Xiaowei SHAO,Xingmin ZHANG,Shengxiu NIU,Lijuan YANG,Yi WU. Synthesis and Biological Activity in vitro of Imidazo[4,5-c]quinoline Derivatives † [J]. Chemical Journal of Chinese Universities, 2019, 40(12): 2502-2511. |
[12] | Yong ZHANG,Cheng SHEN,Zhirong XING,Guiqi CHEN,Zi LU,Zhibing HOU,Xuemei CHEN. Benzimidazole-Derived Fluorescence Enhancement Probe for Visual Detection of HClO † [J]. Chemical Journal of Chinese Universities, 2019, 40(12): 2480-2485. |
[13] | TANG Yucai,QU Huang,ZHANG Wenxi,WANG Feifei,WANG Gang. Synthesis of α-Sulfonyl Ketones via I2/TBHP Promoted Radical Sulfonylation of Silyl Enol Ethers with Sulfohydrazides under Mild Conditions † [J]. Chemical Journal of Chinese Universities, 2020, 41(1): 118-124. |
[14] | ZHANG Jiayi,JIA Mengyang,JIANG Xiaohui,ZHANG Zhiming,YU Liangmin,WANG Xuan. Antifouling Properties of Dodecyl Benzene Sulfonic Acid Doped Polypyrrole Under Alternating Anodic-cathodic Polarization † [J]. Chemical Journal of Chinese Universities, 2019, 40(11): 2396-2403. |
[15] | FANG Fang,XUE Liangmin,CONG Jing,TIAN Chao,WANG Xiaowei,LIU Junyi,ZHANG Zhili. Synthesis and Anti-tumor Activity Evaluation of a Series of 2- or 4-Substituted Pyrido[3,2-d]pyrimidines as Nonclassical Antifolates [J]. Chemical Journal of Chinese Universities, 2019, 40(10): 2111-2120. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||