高等学校化学学报 ›› 2022, Vol. 43 ›› Issue (8): 20220142.doi: 10.7503/cjcu20220142
收稿日期:
2022-03-07
出版日期:
2022-08-10
发布日期:
2022-04-22
通讯作者:
葛怡聪
E-mail:geyc@js.lsnu.edu.cn
基金资助:
GE Yicong(), NIE Wanli, SUN Guofeng, CHEN Jiaxuan, TIAN Chong
Received:
2022-03-07
Online:
2022-08-10
Published:
2022-04-22
Contact:
GE Yicong
E-mail:geyc@js.lsnu.edu.cn
Supported by:
摘要:
利用廉价易得的2-胺基苯乙烯与苯并异噁唑在银催化下发生[5+1]串联环化反应, 以中等至优异的收率一步得到含有N,N-双齿螯合片段的2-喹啉基苯胺衍生物. 该方法具有宽泛的底物普适性、 较高的原子经济性和温和的反应条件等优势, 为合成这类具有广泛用途的N,N-双齿螯合分子提供了新的研究思路.
中图分类号:
TrendMD:
葛怡聪, 聂万丽, 孙国峰, 陈稼轩, 田冲. 银催化2-烯基苯胺与苯并异噁唑的[5+1]环化反应. 高等学校化学学报, 2022, 43(8): 20220142.
GE Yicong, NIE Wanli, SUN Guofeng, CHEN Jiaxuan, TIAN Chong. Silver-catalyzed [5+1] Cyclization of 2-Vinylanilines with Benzisoxazoles. Chem. J. Chinese Universities, 2022, 43(8): 20220142.
Compd. | 1H NMR, δ | 13C NMR, δ |
---|---|---|
3a | 8.18(d, J=8.4 Hz, 1H), 7.94(d, J=8.4 Hz, 1H), 7.83(d, J=1.9 Hz, 1H), 7.80—7.72(m, 2H), 7.65—7.47(m, 6H), 7.30—7.22(m, 1H), 6.87(m, 2H) | 158.7, 149.2, 147.4, 147.3, 138.4, 130.4, 129.9, 129.6, 129.5, 129.2, 128.6, 128.4, 126.2, 125.6, 125.0, 121.6, 120.8, 117.6, 117.4 |
3b | 8.09(d, J=8.6 Hz, 1H), 7.79(d, J=8.3 Hz, 2H), 7.71(s, 1H), 7.61(m, 6H), 7.26(d, J=7.8 Hz, 1H), 6.87(t, J=8.1 Hz, 2H), 2.54(s, 3H) | 157.9, 148.5, 147.4, 145.9, 138.6, 136.2, 131.7, 130.2, 129.8, 129.6, 129.0, 128.6, 128.3, 125.0, 124.5, 121.8, 120.9, 117.5, 117.3, 21.8 |
3c | 8.08(d, J=9.2 Hz, 1H), 7.78(s, 1H), 7.73(d, J=7.8 Hz, 1H), 7.65—7.54(m, 5H), 7.43(dd, J=9.1, 2.8 Hz, 1H), 7.27—7.22(m, 2H), 6.89—6.82(m, 2H), 3.85(s, 3H) | 157.8, 156.4, 147.9, 147.1, 143.3, 138.7, 130.7, 130.0, 129. 7, 129.4, 128.7, 128.4, 125.9, 122.0, 121.7, 121.2, 117.6, 117.3, 103.9, 55.5 |
3d | 8.06(d, J=8.8 Hz, 1H), 7.81(s, 1H), 7.76(d, J=7.8 Hz, 1H), 7.72(d, J=2.2 Hz, 1H), 7.65(d, J=8.9 Hz, 1H), 7.63—7.54(m, 6H), 7.26(t, J=7.6 Hz, 1H), 6.85(t, J=8.4 Hz, 2H), 2.52(s, 3H) | 158.0, 147.8, 147.3, 145.6, 138.2, 136.9, 130.3, 129.7, 129.5, 129.5, 129.0, 128.7, 128.5, 125.4, 121.5, 121.4, 121.2, 117.5, 117.4, 15.9 |
3e | 8.16(m, 1H), 7.86(s, 1H), 7.76(d, J=7.8 Hz, 1H), 7.66—7.48(m, 7H), 7.27(t, J=7.5 Hz, 1H), 6.87(m, 2H) | 161.8, 159.3, 158.2, 148.6, 148.6, 147.3, 144.4, 137.9, 131.6, 131.5, 130.4, 129.8, 129.4, 128.8, 128.7, 125.8, 125.7, 121.5, 121.4, 119.7, 119.5, 117.6, 117.4, 109.3, 109.1 |
3f | 8.08—7.97(m, 2H), 7.85—7.78(m, 2H), 7.76(m, 1H), 7.60(m, 5H), 7.30—7.23(m, 1H), 6.85(m, 2H), 6.25(s, 2H) | 159.1, 148.2, 147.5, 146.0, 137.7, 133.0, 130.9, 130.6, 129.9, 129.5, 128.9, 128.7, 127.8, 126.2, 121.6, 121.0, 120.2, 117.6, 117.4 |
3g | 8.22(d, J=9.1 Hz, 1H), 7.91(s, 1H), 7.79(s, 2H), 7.68—7.58(m, 6H), 7.30(t, J=9.0 Hz, 1H), 6.88(m, 2H) | 159.3, 149.0, 147.4, 146.9, 145.7, 137.6, 131.2, 130.7, 129.8, 129.4, 128.9, 128.8, 125.3, 124.4, 123.4, 121.9, 121.7, 121.1, 119.3, 117.7, 117.7, 117.5, 116.8, 116.5 |
3h | 8.71(d, J=1.9 Hz, 1H), 8.35(dd, J=8.8, 1.9 Hz, 1H), 8.17(d, J=8.8 Hz, 1H), 7.89(s, 1H), 7.80(d, J=7.8 Hz, 1H), 7.64—7.57(m, 5H), 7.28(t, J=8.4 Hz, 1H), 6.89—6.81(m, 2H), 6.37(s, 2H), 4.45(q, J=7.1 Hz, 2H), 1.45(t, J=7.1 Hz, 3H) | 166.4, 160.7, 150.2, 149.4, 147.9, 137.7, 130.9, 130.0, 129.6, 129.3, 129.1, 128.9, 128.8, 128.8, 127.9, 124.2, 121.4, 120.8, 117.5, 61.3, 14.4 |
3i | 7.90(d, J=1.9 Hz, 1H), 7.87—7.82(m, 1H), 7.62—7.53(m, 5H), 7.48(d, J=8.4 Hz, 1H), 7.44—7.38(m, 1H), 7.25(t, J=7.6 Hz, 1H), 7.11(d, J=7.6 Hz, 1H), 6.91(d, J=8.1 Hz, 1H), 6.83(t, J=7.6 Hz, 1H), 4.14(s, 3H) | 156.9, 155.3, 148.9, 147.5, 139.0, 138.8, 130.3, 129.6, 129.2, 128.5, 128.3, 126.0, 125.9, 121.1, 120.5, 117.9, 117.3, 107.7, 56.1 |
Compd. | 1H NMR, δ | 13C NMR, δ |
3j | 7.89—7.84(m, 2H), 7.68(d, J=8.5 Hz, 1H), 7.61—7.53(m, 5H), 7.29—7.22(m, 2H), 6.91—6.82(m, 2H), 6.60(s, 1H), 3.41(t, J=6.3 Hz, 2H), 3.01(t, J=6.2 Hz, 2H), 2.11—2.02(m, 2H), 1.99(m, 2H) | 157.1, 149.0, 147.7, 146.2, 139.0, 138.4, 134.1, 130.1, 129.6, 128.5, 128.3, 128.2, 123.0, 122.5, 121.4, 119.3, 117.4, 117.2, 30.3, 25.4, 23.2, 22.9 |
3k | 9.30(d, J=7.7 Hz, 1H), 8.00—7.92(m, 2H), 7.89—7.73(m, 5H), 7.65—7.58(m, 5H), 7.30(t, J=7.5 Hz, 1H), 6.98—6.85(m, 2H), 6.29(s, 2H) | 157.4, 149.3, 147.0, 145.5, 138.7, 133.7, 131.4, 130.3, 130.1, 129.7, 128.7, 128.4, 128.2, 128.0, 127.1, 124.5, 123.0, 122.5, 122.5, 121.8, 117.8, 117.4 |
3l | 7.70(d, J=7.8 Hz, 1H), 7.66(s, 1H), 7.61—7.52(m, 5H), 7.47(s, 1H), 7.23(d, J=7.6 Hz, 1H), 7.19(s, 1H), 6.84(t, J=8.3 Hz, 2H), 6.12(s, 2H) | 156.8, 150.5, 148.2, 147.9, 147.0, 145.6, 138.8, 129.9, 129.7, 129.3, 128.6, 128.3, 122.1, 121.7, 119.5, 117.6, 117.3, 105.7, 101.7, 101.2 |
3m | 8.17(d, J=8.4 Hz, 1H), 7.96(d, J=8.4 Hz, 1H), 7.82(s, 1H), 7.80—7.72(m, 2H), 7.50(m, 2H), 7.44—7.35(m, 3H), 7.27(d, J=7.6 Hz, 1H), 6.86(t, J=8.4 Hz, 2H), 2.52(s, 3H) | 158.7, 149.3, 147.4, 147.3, 138.4, 138.3, 130.3, 130.2, 129.9, 129.5, 129.2, 128.5, 126.7, 126.2, 125.8, 125.1, 121.6, 120.8, 117.5, 117.4, 21.6 |
3n | 8.18(d, J=8.5 Hz, 1H), 8.00(d, J=8.5 Hz, 1H), 7.78—7.82(m, 3H), 7.58—7.48(m, 3H), 7.28(t, J=8.3 Hz, 1H), 7.13(d, J=9.1 Hz, 2H), 6.86(d, J=8.5 Hz, 2H), 3.97(s, 3H) | 156.9, 155.3, 148.9, 147.5, 139.0, 138.8, 130.3, 129.6, 129.5, 129.2, 128.5, 128.3, 126.0, 125.9, 121.1, 120.5, 117.9, 117.3, 107.7, 56.1 |
3o | 8.17(d, J=8.4 Hz, 1H), 7.88(d, J=8.3 Hz, 1H), 7.83—7.71(m, 3H), 7.62—7.50(m, 5H), 7.31—7.23(m, 1H), 6.87(d, J=7.8 Hz, 2H), 6.26(s, 2H) | 158.8, 147. 8, 147.5, 147.4, 136.8, 134.6, 130.9, 130.5, 129.9, 129.7, 129.3, 128.9, 126.4, 125.3, 124.7, 121.4, 120.8, 117.5, 117.4 |
3p | 8.21(d, J=8.4 Hz, 1H), 8.04(dd, J=14.1, 8.2 Hz, 2H), 7.95(s, 1H), 7.75(m, 2H), 7.68(t, J=7.4 Hz, 1H), 7.62—7.45(m, 4H), 7.44—7.23(m, 3H), 6.89(d, J=8.0 Hz, 1H), 6.82(t, J=7.4 Hz, 1H), 6.39(s, 2H) | 158.8, 148.0, 147.0, 135.9, 133.5, 132.0, 130.5, 130.0, 129.7, 129.1, 128.8, 128.4, 127.5, 126.6, 126.3, 126.2, 126.1, 125.4, 117.7 |
3q | 8.24(d, J=8.4 Hz, 1H), 8.09(d, J=8.4 Hz, 1H), 7.87(s, 1H), 7.72(m, 2H), 7.55—7.49(m, 2H), 7.41(d, J=3.5 Hz, 1H), 7.25—7.18(m, 2H), 6.81(m, 2H), 6.15(s, 1H) | 158.8, 147.6, 147.5, 141.5, 139.3, 130.4, 129.8, 129.7, 129.4, 128.5, 127.8, 127.1, 126.5, 125.3, 124.7, 121.4, 121.3, 117.5, 117.3 |
3r | 8.13(d, J=8.4 Hz, 1H), 7.91(d, J=8.4 Hz, 1H), 7.82—7.71(m, 3H), 7.58—7.47(m, 6H), 7.06—6.98(m, 2H) | 157.5, 149.7, 147.6, 147.2, 138.1, 132.5, 132.2, 131.8, 131.5, 130.3, 129.9, 129.6, 129.3, 129.2, 128.9, 128.7, 128.6, 128.2, 126.8, 125.8, 125.5, 125.3, 123.9, 122.8, 120.7, 120.1, 113.9, 113.8, 113.8, 113.7, 113.6, 113.5, 113.5, 113.5 |
3s | 8.18(d, J=8.4 Hz, 1H), 7.95(d, J=8.5 Hz, 1H), 7.85—7.75(m, 3H), 7.61—7.52(m, 7H), 7.48(d, J=8.2 Hz, 1H), 3.97(s, 3H) | 167.1, 157.7, 149.5, 147.3, 138.1, 131.4, 129.9, 129.8, 129.5, 129.3, 128.7, 128.6, 126.7, 125.7, 125.2, 125.2, 120.8, 118.4, 118.1, 52.1 |
3t | 8.15(d, J=8.2 Hz, 1H), 7.94(d, J=8.2 Hz, 1H), 7.80—7.71(m, 3H), 7.62—7.56(m, 5H), 7.52(t, J=7.2 Hz, 1H), 6.60—6.51(m, 2H) | 165.4, 163.0, 158.0, 149.6, 149.5, 149.2, 147.2, 138.2, 131.68, 131.5, 129.63, 129.53, 129.02, 128.64, 128.49, 126.23, 125.67, 124.89, 120.51, 117.67, 104.67, 104.45, 103.22, 102.98 |
3u | 8.16(d, J=8.3 Hz, 1H), 7.94(d, J=8.3 Hz, 1H), 7.81—7.74(m, 2H), 7.65—7.51(m, 7H), 7.02(d, J=2.1 Hz, 1H), 6.95(d, J=8.4 Hz, 1H) | 157.8, 149.4, 148.7, 147.1, 138.1, 131.1, 129.8, 129.5, 129.0, 128.7, 128.6, 126.5, 125.7, 125.0, 124.3, 120.4, 120.3, 120.0, 119.6. |
3v | 8.16(d, J=8.4 Hz, 1H), 7.95(d, J=8.4 Hz, 1H), 7.81—7.73(m, 3H), 7.63—7.51(m, 6H), 7.20(d, J=8.7 Hz, 1H), 6.80(d, J=8.5 Hz, 1H) | 157.4, 149.5, 147.3, 146.1, 138.1, 130.1, 129.7, 129.5, 129.2, 128.7, 128.6, 126.5, 125.7, 125.1, 122.5, 121.9, 120.4, 118.5 |
3w | 8.20(d, J=8.5 Hz, 1H), 8.00(d, J=8.4 Hz, 1H), 7.82—7.72(m, 2H), 7.63—7.55(m, 6H), 7.19(t, J=8.1 Hz, 1H), 6.69—6.56(m, 2H) | 154.1, 148.7, 148.2, 148.1, 147.8, 138.1, 130.6, 130.5, 129.7, 129.5, 129.3, 128.6, 128.5, 126.7, 125.8, 125.5, 124.6, 124.6, 112.4, 112.2, 104.9, 104.6 |
3x | 8.11(d, J=8.4 Hz, 1H), 7.90(d, J=8.5 Hz, 1H), 7.73(t, J=8.3Hz, 1H), 7.68(s, 1H), 7.61–7.53(m, 5H), 7.48(t, J=8.2 Hz, 1H), 7.26(s, 1H), 6.42(s, 1H), 6.30(s, 2H), 5.95(s, 2H) | 158.5, 149.4, 149.0, 147.4, 144.2, 140.2, 138.5, 129.5, 129.4, 128.9, 128.6, 128.4, 125.8, 125.6, 124.7, 120.4, 113.5, 108.4, 100.9, 98.4 |
Table 1 1H NMR and 13C NMR data of compounds 3a—3x
Compd. | 1H NMR, δ | 13C NMR, δ |
---|---|---|
3a | 8.18(d, J=8.4 Hz, 1H), 7.94(d, J=8.4 Hz, 1H), 7.83(d, J=1.9 Hz, 1H), 7.80—7.72(m, 2H), 7.65—7.47(m, 6H), 7.30—7.22(m, 1H), 6.87(m, 2H) | 158.7, 149.2, 147.4, 147.3, 138.4, 130.4, 129.9, 129.6, 129.5, 129.2, 128.6, 128.4, 126.2, 125.6, 125.0, 121.6, 120.8, 117.6, 117.4 |
3b | 8.09(d, J=8.6 Hz, 1H), 7.79(d, J=8.3 Hz, 2H), 7.71(s, 1H), 7.61(m, 6H), 7.26(d, J=7.8 Hz, 1H), 6.87(t, J=8.1 Hz, 2H), 2.54(s, 3H) | 157.9, 148.5, 147.4, 145.9, 138.6, 136.2, 131.7, 130.2, 129.8, 129.6, 129.0, 128.6, 128.3, 125.0, 124.5, 121.8, 120.9, 117.5, 117.3, 21.8 |
3c | 8.08(d, J=9.2 Hz, 1H), 7.78(s, 1H), 7.73(d, J=7.8 Hz, 1H), 7.65—7.54(m, 5H), 7.43(dd, J=9.1, 2.8 Hz, 1H), 7.27—7.22(m, 2H), 6.89—6.82(m, 2H), 3.85(s, 3H) | 157.8, 156.4, 147.9, 147.1, 143.3, 138.7, 130.7, 130.0, 129. 7, 129.4, 128.7, 128.4, 125.9, 122.0, 121.7, 121.2, 117.6, 117.3, 103.9, 55.5 |
3d | 8.06(d, J=8.8 Hz, 1H), 7.81(s, 1H), 7.76(d, J=7.8 Hz, 1H), 7.72(d, J=2.2 Hz, 1H), 7.65(d, J=8.9 Hz, 1H), 7.63—7.54(m, 6H), 7.26(t, J=7.6 Hz, 1H), 6.85(t, J=8.4 Hz, 2H), 2.52(s, 3H) | 158.0, 147.8, 147.3, 145.6, 138.2, 136.9, 130.3, 129.7, 129.5, 129.5, 129.0, 128.7, 128.5, 125.4, 121.5, 121.4, 121.2, 117.5, 117.4, 15.9 |
3e | 8.16(m, 1H), 7.86(s, 1H), 7.76(d, J=7.8 Hz, 1H), 7.66—7.48(m, 7H), 7.27(t, J=7.5 Hz, 1H), 6.87(m, 2H) | 161.8, 159.3, 158.2, 148.6, 148.6, 147.3, 144.4, 137.9, 131.6, 131.5, 130.4, 129.8, 129.4, 128.8, 128.7, 125.8, 125.7, 121.5, 121.4, 119.7, 119.5, 117.6, 117.4, 109.3, 109.1 |
3f | 8.08—7.97(m, 2H), 7.85—7.78(m, 2H), 7.76(m, 1H), 7.60(m, 5H), 7.30—7.23(m, 1H), 6.85(m, 2H), 6.25(s, 2H) | 159.1, 148.2, 147.5, 146.0, 137.7, 133.0, 130.9, 130.6, 129.9, 129.5, 128.9, 128.7, 127.8, 126.2, 121.6, 121.0, 120.2, 117.6, 117.4 |
3g | 8.22(d, J=9.1 Hz, 1H), 7.91(s, 1H), 7.79(s, 2H), 7.68—7.58(m, 6H), 7.30(t, J=9.0 Hz, 1H), 6.88(m, 2H) | 159.3, 149.0, 147.4, 146.9, 145.7, 137.6, 131.2, 130.7, 129.8, 129.4, 128.9, 128.8, 125.3, 124.4, 123.4, 121.9, 121.7, 121.1, 119.3, 117.7, 117.7, 117.5, 116.8, 116.5 |
3h | 8.71(d, J=1.9 Hz, 1H), 8.35(dd, J=8.8, 1.9 Hz, 1H), 8.17(d, J=8.8 Hz, 1H), 7.89(s, 1H), 7.80(d, J=7.8 Hz, 1H), 7.64—7.57(m, 5H), 7.28(t, J=8.4 Hz, 1H), 6.89—6.81(m, 2H), 6.37(s, 2H), 4.45(q, J=7.1 Hz, 2H), 1.45(t, J=7.1 Hz, 3H) | 166.4, 160.7, 150.2, 149.4, 147.9, 137.7, 130.9, 130.0, 129.6, 129.3, 129.1, 128.9, 128.8, 128.8, 127.9, 124.2, 121.4, 120.8, 117.5, 61.3, 14.4 |
3i | 7.90(d, J=1.9 Hz, 1H), 7.87—7.82(m, 1H), 7.62—7.53(m, 5H), 7.48(d, J=8.4 Hz, 1H), 7.44—7.38(m, 1H), 7.25(t, J=7.6 Hz, 1H), 7.11(d, J=7.6 Hz, 1H), 6.91(d, J=8.1 Hz, 1H), 6.83(t, J=7.6 Hz, 1H), 4.14(s, 3H) | 156.9, 155.3, 148.9, 147.5, 139.0, 138.8, 130.3, 129.6, 129.2, 128.5, 128.3, 126.0, 125.9, 121.1, 120.5, 117.9, 117.3, 107.7, 56.1 |
Compd. | 1H NMR, δ | 13C NMR, δ |
3j | 7.89—7.84(m, 2H), 7.68(d, J=8.5 Hz, 1H), 7.61—7.53(m, 5H), 7.29—7.22(m, 2H), 6.91—6.82(m, 2H), 6.60(s, 1H), 3.41(t, J=6.3 Hz, 2H), 3.01(t, J=6.2 Hz, 2H), 2.11—2.02(m, 2H), 1.99(m, 2H) | 157.1, 149.0, 147.7, 146.2, 139.0, 138.4, 134.1, 130.1, 129.6, 128.5, 128.3, 128.2, 123.0, 122.5, 121.4, 119.3, 117.4, 117.2, 30.3, 25.4, 23.2, 22.9 |
3k | 9.30(d, J=7.7 Hz, 1H), 8.00—7.92(m, 2H), 7.89—7.73(m, 5H), 7.65—7.58(m, 5H), 7.30(t, J=7.5 Hz, 1H), 6.98—6.85(m, 2H), 6.29(s, 2H) | 157.4, 149.3, 147.0, 145.5, 138.7, 133.7, 131.4, 130.3, 130.1, 129.7, 128.7, 128.4, 128.2, 128.0, 127.1, 124.5, 123.0, 122.5, 122.5, 121.8, 117.8, 117.4 |
3l | 7.70(d, J=7.8 Hz, 1H), 7.66(s, 1H), 7.61—7.52(m, 5H), 7.47(s, 1H), 7.23(d, J=7.6 Hz, 1H), 7.19(s, 1H), 6.84(t, J=8.3 Hz, 2H), 6.12(s, 2H) | 156.8, 150.5, 148.2, 147.9, 147.0, 145.6, 138.8, 129.9, 129.7, 129.3, 128.6, 128.3, 122.1, 121.7, 119.5, 117.6, 117.3, 105.7, 101.7, 101.2 |
3m | 8.17(d, J=8.4 Hz, 1H), 7.96(d, J=8.4 Hz, 1H), 7.82(s, 1H), 7.80—7.72(m, 2H), 7.50(m, 2H), 7.44—7.35(m, 3H), 7.27(d, J=7.6 Hz, 1H), 6.86(t, J=8.4 Hz, 2H), 2.52(s, 3H) | 158.7, 149.3, 147.4, 147.3, 138.4, 138.3, 130.3, 130.2, 129.9, 129.5, 129.2, 128.5, 126.7, 126.2, 125.8, 125.1, 121.6, 120.8, 117.5, 117.4, 21.6 |
3n | 8.18(d, J=8.5 Hz, 1H), 8.00(d, J=8.5 Hz, 1H), 7.78—7.82(m, 3H), 7.58—7.48(m, 3H), 7.28(t, J=8.3 Hz, 1H), 7.13(d, J=9.1 Hz, 2H), 6.86(d, J=8.5 Hz, 2H), 3.97(s, 3H) | 156.9, 155.3, 148.9, 147.5, 139.0, 138.8, 130.3, 129.6, 129.5, 129.2, 128.5, 128.3, 126.0, 125.9, 121.1, 120.5, 117.9, 117.3, 107.7, 56.1 |
3o | 8.17(d, J=8.4 Hz, 1H), 7.88(d, J=8.3 Hz, 1H), 7.83—7.71(m, 3H), 7.62—7.50(m, 5H), 7.31—7.23(m, 1H), 6.87(d, J=7.8 Hz, 2H), 6.26(s, 2H) | 158.8, 147. 8, 147.5, 147.4, 136.8, 134.6, 130.9, 130.5, 129.9, 129.7, 129.3, 128.9, 126.4, 125.3, 124.7, 121.4, 120.8, 117.5, 117.4 |
3p | 8.21(d, J=8.4 Hz, 1H), 8.04(dd, J=14.1, 8.2 Hz, 2H), 7.95(s, 1H), 7.75(m, 2H), 7.68(t, J=7.4 Hz, 1H), 7.62—7.45(m, 4H), 7.44—7.23(m, 3H), 6.89(d, J=8.0 Hz, 1H), 6.82(t, J=7.4 Hz, 1H), 6.39(s, 2H) | 158.8, 148.0, 147.0, 135.9, 133.5, 132.0, 130.5, 130.0, 129.7, 129.1, 128.8, 128.4, 127.5, 126.6, 126.3, 126.2, 126.1, 125.4, 117.7 |
3q | 8.24(d, J=8.4 Hz, 1H), 8.09(d, J=8.4 Hz, 1H), 7.87(s, 1H), 7.72(m, 2H), 7.55—7.49(m, 2H), 7.41(d, J=3.5 Hz, 1H), 7.25—7.18(m, 2H), 6.81(m, 2H), 6.15(s, 1H) | 158.8, 147.6, 147.5, 141.5, 139.3, 130.4, 129.8, 129.7, 129.4, 128.5, 127.8, 127.1, 126.5, 125.3, 124.7, 121.4, 121.3, 117.5, 117.3 |
3r | 8.13(d, J=8.4 Hz, 1H), 7.91(d, J=8.4 Hz, 1H), 7.82—7.71(m, 3H), 7.58—7.47(m, 6H), 7.06—6.98(m, 2H) | 157.5, 149.7, 147.6, 147.2, 138.1, 132.5, 132.2, 131.8, 131.5, 130.3, 129.9, 129.6, 129.3, 129.2, 128.9, 128.7, 128.6, 128.2, 126.8, 125.8, 125.5, 125.3, 123.9, 122.8, 120.7, 120.1, 113.9, 113.8, 113.8, 113.7, 113.6, 113.5, 113.5, 113.5 |
3s | 8.18(d, J=8.4 Hz, 1H), 7.95(d, J=8.5 Hz, 1H), 7.85—7.75(m, 3H), 7.61—7.52(m, 7H), 7.48(d, J=8.2 Hz, 1H), 3.97(s, 3H) | 167.1, 157.7, 149.5, 147.3, 138.1, 131.4, 129.9, 129.8, 129.5, 129.3, 128.7, 128.6, 126.7, 125.7, 125.2, 125.2, 120.8, 118.4, 118.1, 52.1 |
3t | 8.15(d, J=8.2 Hz, 1H), 7.94(d, J=8.2 Hz, 1H), 7.80—7.71(m, 3H), 7.62—7.56(m, 5H), 7.52(t, J=7.2 Hz, 1H), 6.60—6.51(m, 2H) | 165.4, 163.0, 158.0, 149.6, 149.5, 149.2, 147.2, 138.2, 131.68, 131.5, 129.63, 129.53, 129.02, 128.64, 128.49, 126.23, 125.67, 124.89, 120.51, 117.67, 104.67, 104.45, 103.22, 102.98 |
3u | 8.16(d, J=8.3 Hz, 1H), 7.94(d, J=8.3 Hz, 1H), 7.81—7.74(m, 2H), 7.65—7.51(m, 7H), 7.02(d, J=2.1 Hz, 1H), 6.95(d, J=8.4 Hz, 1H) | 157.8, 149.4, 148.7, 147.1, 138.1, 131.1, 129.8, 129.5, 129.0, 128.7, 128.6, 126.5, 125.7, 125.0, 124.3, 120.4, 120.3, 120.0, 119.6. |
3v | 8.16(d, J=8.4 Hz, 1H), 7.95(d, J=8.4 Hz, 1H), 7.81—7.73(m, 3H), 7.63—7.51(m, 6H), 7.20(d, J=8.7 Hz, 1H), 6.80(d, J=8.5 Hz, 1H) | 157.4, 149.5, 147.3, 146.1, 138.1, 130.1, 129.7, 129.5, 129.2, 128.7, 128.6, 126.5, 125.7, 125.1, 122.5, 121.9, 120.4, 118.5 |
3w | 8.20(d, J=8.5 Hz, 1H), 8.00(d, J=8.4 Hz, 1H), 7.82—7.72(m, 2H), 7.63—7.55(m, 6H), 7.19(t, J=8.1 Hz, 1H), 6.69—6.56(m, 2H) | 154.1, 148.7, 148.2, 148.1, 147.8, 138.1, 130.6, 130.5, 129.7, 129.5, 129.3, 128.6, 128.5, 126.7, 125.8, 125.5, 124.6, 124.6, 112.4, 112.2, 104.9, 104.6 |
3x | 8.11(d, J=8.4 Hz, 1H), 7.90(d, J=8.5 Hz, 1H), 7.73(t, J=8.3Hz, 1H), 7.68(s, 1H), 7.61–7.53(m, 5H), 7.48(t, J=8.2 Hz, 1H), 7.26(s, 1H), 6.42(s, 1H), 6.30(s, 2H), 5.95(s, 2H) | 158.5, 149.4, 149.0, 147.4, 144.2, 140.2, 138.5, 129.5, 129.4, 128.9, 128.6, 128.4, 125.8, 125.6, 124.7, 120.4, 113.5, 108.4, 100.9, 98.4 |
Compd. | Yield(%) | HRMS(calcd.), m/z | IR(KBr), |
---|---|---|---|
3a | 75 | 297.1386, 297.1393[M+H] | 3454, 3058, 1582, 1546, 1261, 749, 701 |
3b | 73 | 311.1543, 311.1556[M+H] | 3454, 3054, 1583, 1546, 1261, 744, 703 |
3c | 76 | 327.1492, 327.1399[M+H] | 3454, 3060, 1616, 1546, 1263, 1227, 833, 743 |
3d | 80 | 343.1264, 343.1266[M+H] | 3520, 1693, 1546, 1532, 1463, 1263, 1072, 742 |
3e | 67 | 315.1292, 315.1301[M+H] | 3459, 3063, 1615, 1546, 1497, 1228, 747, 704 |
3f | 58 | 375.0492, 375.0491[M+H] | 3457, 3061, 1583, 1535, 1254, 745, 701 |
3g | 47 | 403.1028, 403.1028[M+Na] | 3458, 3065, 1546, 1259, 1084, 747, 710 |
3h | 52 | 369.1598, 369.1588[M+H] | 3452, 2981, 1710, 1583, 1276, 1155, 761 |
3i | 74 | 327.1492, 327.1489[M+H] | 3467,3059, 1548, 1467, 1260, 1097, 748, 702 |
3j | 68 | 351.1856, 351.1847[M+Na] | 3456, 3057, 2929, 1610, 1545, 1461, 1259, 743 |
3k | 76 | 347.1543, 347.1546[M+H] | 3456, 3057, 1714, 1580, 1546, 1501, 749, 702 |
3l | 69 | 363.1104, 363.1110[M+Na] | 3579, 3058, 1552, 1461, 1211, 1036, 747, 702 |
3m | 76 | 311.1543, 311.1538[M+H] | 3456, 3064, 1583, 1546, 1255, 1158, 756 |
3n | 82 | 327.1492, 327.1492[M+H] | 3455, 3057, 1607, 1506, 1256, 1031, 741 |
3o | 74 | 331.0997, 331.0990[M+H] | 3479, 3056, 1603, 1546, 1264, 1084, 741 |
3p | 71 | 347.1543, 347.1551[M+H] | 3461, 3060, 1693, 1546, 1512, 1259, 751 |
3q | 45 | 303.0951, 303.0947[M+H] | 3520, 3060, 1693, 1647, 1546, 1512, 912, 744 |
3r | 82 | 387.1079, 387.1082[M+Na] | 3580, 3060, 1587, 1546, 1203, 1037, 769, 742 |
3s | 84 | 355.1441, 355.1449[M+H] | 3451, 3060, 1714, 1582, 1241, 1084, 767, 701 |
3t | 75 | 315.1292, 315.1289[M+H] | 3459, 3062, 1608, 1582, 1243, 1084, 767, 701 |
3u | 77 | 397.0311, 397.0302[M+Na] | 3458, 3062, 1597, 1536, 1251, 890, 767, 700 |
3v | 89 | 353.0816, 353.0814[M+Na] | 3458, 3059, 1582, 1545, 1259, 765, 702 |
3w | 62 | 315.1292, 315.1299[M+H] | 3520, 3057, 1582, 1547, 1264, 1241, 740, 703 |
3x | 51 | 341.1285, 341.1286[M+H] | 3487, 3060, 1546, 1511, 1223, 1037, 767 |
Table 2 Yields, HRMS and IR data of compounds 3a—3x
Compd. | Yield(%) | HRMS(calcd.), m/z | IR(KBr), |
---|---|---|---|
3a | 75 | 297.1386, 297.1393[M+H] | 3454, 3058, 1582, 1546, 1261, 749, 701 |
3b | 73 | 311.1543, 311.1556[M+H] | 3454, 3054, 1583, 1546, 1261, 744, 703 |
3c | 76 | 327.1492, 327.1399[M+H] | 3454, 3060, 1616, 1546, 1263, 1227, 833, 743 |
3d | 80 | 343.1264, 343.1266[M+H] | 3520, 1693, 1546, 1532, 1463, 1263, 1072, 742 |
3e | 67 | 315.1292, 315.1301[M+H] | 3459, 3063, 1615, 1546, 1497, 1228, 747, 704 |
3f | 58 | 375.0492, 375.0491[M+H] | 3457, 3061, 1583, 1535, 1254, 745, 701 |
3g | 47 | 403.1028, 403.1028[M+Na] | 3458, 3065, 1546, 1259, 1084, 747, 710 |
3h | 52 | 369.1598, 369.1588[M+H] | 3452, 2981, 1710, 1583, 1276, 1155, 761 |
3i | 74 | 327.1492, 327.1489[M+H] | 3467,3059, 1548, 1467, 1260, 1097, 748, 702 |
3j | 68 | 351.1856, 351.1847[M+Na] | 3456, 3057, 2929, 1610, 1545, 1461, 1259, 743 |
3k | 76 | 347.1543, 347.1546[M+H] | 3456, 3057, 1714, 1580, 1546, 1501, 749, 702 |
3l | 69 | 363.1104, 363.1110[M+Na] | 3579, 3058, 1552, 1461, 1211, 1036, 747, 702 |
3m | 76 | 311.1543, 311.1538[M+H] | 3456, 3064, 1583, 1546, 1255, 1158, 756 |
3n | 82 | 327.1492, 327.1492[M+H] | 3455, 3057, 1607, 1506, 1256, 1031, 741 |
3o | 74 | 331.0997, 331.0990[M+H] | 3479, 3056, 1603, 1546, 1264, 1084, 741 |
3p | 71 | 347.1543, 347.1551[M+H] | 3461, 3060, 1693, 1546, 1512, 1259, 751 |
3q | 45 | 303.0951, 303.0947[M+H] | 3520, 3060, 1693, 1647, 1546, 1512, 912, 744 |
3r | 82 | 387.1079, 387.1082[M+Na] | 3580, 3060, 1587, 1546, 1203, 1037, 769, 742 |
3s | 84 | 355.1441, 355.1449[M+H] | 3451, 3060, 1714, 1582, 1241, 1084, 767, 701 |
3t | 75 | 315.1292, 315.1289[M+H] | 3459, 3062, 1608, 1582, 1243, 1084, 767, 701 |
3u | 77 | 397.0311, 397.0302[M+Na] | 3458, 3062, 1597, 1536, 1251, 890, 767, 700 |
3v | 89 | 353.0816, 353.0814[M+Na] | 3458, 3059, 1582, 1545, 1259, 765, 702 |
3w | 62 | 315.1292, 315.1299[M+H] | 3520, 3057, 1582, 1547, 1264, 1241, 740, 703 |
3x | 51 | 341.1285, 341.1286[M+H] | 3487, 3060, 1546, 1511, 1223, 1037, 767 |
Entry | Catalyst | Solvent | Temperature/℃ | Yield b (%) |
---|---|---|---|---|
1 | AgOAc | 1,4?Dioxane | 80 | 29 |
2 | AgOTf | 1,4?Dioxane | 80 | 48 |
3 | Ag(NTf)2 | 1,4?Dioxane | 80 | 37 |
4 | AgSbF6 | 1,4?Dioxane | 80 | 36 |
5 | AgCl | 1,4?Dioxane | 80 | trace |
6 | Ag2CO3 | 1,4?Dioxane | 80 | 21 |
7 | — | 1,4?Dioxane | 80 | N. D. g |
8 | AgOTf | Toluene | 80 | 52 |
9 | AgOTf | MeCN | 80 | trace |
10 | AgOTf | THF | 80 | 19 |
11 | AgOTf | HFIP | 80 | 68 |
12 | AgOTf | HFIP | 70 | 62 |
13 | AgOTf | HFIP | 90(100) | 75(73) |
14 c | AgOTf | HFIP | 90 | N. D. |
15 d | AgOTf | HFIP | 90 | 26 |
16 e | AgOTf | HFIP | 90 | 67 |
17 f | AgOTf | HFIP | 90 | 54 |
Table 3 Optimization of the reaction conditions a
Entry | Catalyst | Solvent | Temperature/℃ | Yield b (%) |
---|---|---|---|---|
1 | AgOAc | 1,4?Dioxane | 80 | 29 |
2 | AgOTf | 1,4?Dioxane | 80 | 48 |
3 | Ag(NTf)2 | 1,4?Dioxane | 80 | 37 |
4 | AgSbF6 | 1,4?Dioxane | 80 | 36 |
5 | AgCl | 1,4?Dioxane | 80 | trace |
6 | Ag2CO3 | 1,4?Dioxane | 80 | 21 |
7 | — | 1,4?Dioxane | 80 | N. D. g |
8 | AgOTf | Toluene | 80 | 52 |
9 | AgOTf | MeCN | 80 | trace |
10 | AgOTf | THF | 80 | 19 |
11 | AgOTf | HFIP | 80 | 68 |
12 | AgOTf | HFIP | 70 | 62 |
13 | AgOTf | HFIP | 90(100) | 75(73) |
14 c | AgOTf | HFIP | 90 | N. D. |
15 d | AgOTf | HFIP | 90 | 26 |
16 e | AgOTf | HFIP | 90 | 67 |
17 f | AgOTf | HFIP | 90 | 54 |
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