高等学校化学学报 ›› 2015, Vol. 36 ›› Issue (1): 93.doi: 10.7503/cjcu20140434
收稿日期:
2014-05-08
修回日期:
2014-12-15
出版日期:
2015-01-10
发布日期:
2014-12-15
作者简介:
联系人简介:白银娟, 女, 博士,教授, 博士生导师,主要从事氮杂环合成研究.E-mail:基金资助:
GAO Qi, CHEN Bang, HOU Xiaomeng, BAI Yinjuan*(), SONG Yang, TANG Xuesong
Received:
2014-05-08
Revised:
2014-12-15
Online:
2015-01-10
Published:
2014-12-15
Contact:
BAI Yinjuan
E-mail:baiyinjuan@nwu.edu.cn
Supported by:
摘要:
以自制的4,4'-双甲酰基二苯醚类化合物、 β-酮酸酯及脲为原料, 在FeC13·6H2O的催化下, 通过Biginelli反应合成了12种新型双嘧啶酮二苯醚类衍生物(6a~6l), 探讨了双嘧啶酮合成的反应历程并对反应条件进行优化. 另外, 对4,4'-双甲酰基二苯醚类化合物的合成方法进行了改进, 通过控制对氟苯甲醛的加入时间, 提高了产率, 并大大缩短了反应时间.对所有化合物进行了室内毒力测试, 结果表明, 化合物6d, 6h和6i的抗菌效果较好, 对西瓜枯萎病的EC95值均小于对照药三唑酮; 当取代基R2为CF3时, 化合物的杀菌抑菌活性较好.
中图分类号:
TrendMD:
高旗, 陈邦, 侯晓萌, 白银娟, 宋阳, 唐雪松. 新型双嘧啶酮二苯醚的合成. 高等学校化学学报, 2015, 36(1): 93.
GAO Qi, CHEN Bang, HOU Xiaomeng, BAI Yinjuan, SONG Yang, TANG Xuesong. Synthesis of Novel Dipyrimidinone Diphenyl Ethers†. Chem. J. Chinese Universities, 2015, 36(1): 93.
Compd. | Appearance | Yield(%) | m.p./℃ | HRMS(ESI) [M+Na]+(calcd.), m/z |
---|---|---|---|---|
3a | White solid | 93—95 | 63—64(59.5—64[ | |
3b | Pale yellow viscous liquid | 90—91 | 283.0131(283.0132) | |
3c | White solid | 95—96 | 79—80 | 283.0130(283.0132) |
3d | White solid | 92—94 | 75—76 | 317.0383(317.0396) |
Table 1 Appearance, yields, melting points and HRMS data for compounds 3a—3d
Compd. | Appearance | Yield(%) | m.p./℃ | HRMS(ESI) [M+Na]+(calcd.), m/z |
---|---|---|---|---|
3a | White solid | 93—95 | 63—64(59.5—64[ | |
3b | Pale yellow viscous liquid | 90—91 | 283.0131(283.0132) | |
3c | White solid | 95—96 | 79—80 | 283.0130(283.0132) |
3d | White solid | 92—94 | 75—76 | 317.0383(317.0396) |
Compd. | Appearance | Yield(%) | m.p./℃ | HRMS(ESI)[M+Na]+ (calcd.), m/z | IR(KBr), /cm-1 |
---|---|---|---|---|---|
6a | Pale yellow solid | 86 | 182—184 | 529.1690(529.1694) | 3236, 3120, 2949, 1702, 1642, 1602, 1500, 1434, |
1232, 1090, 875, 758, 655 | |||||
6b | White solid | 85 | 185—187 | 563.1295(563.1304) | 3248, 2950, 1702, 1645, 1604, 1488, 1434, 1384, |
1319, 1231, 1092, 757 | |||||
6c | White solid | 84 | 189—190 | 563.1296(563.1304) | 3242, 3116, 2950, 1704, 1644, 1593, 1480, 1319, |
1232, 1092, 917, 761, 659 | |||||
6d | Pale yellow solid | 81 | 171—173 | 597.1591(597.1568) | 3247, 2952, 1705, 1644, 1601, 1497, 1432, 1316, |
1235, 1162, 1093, 923, 763, 662 | |||||
6e | Pale yellow solid | 84 | 163—164 | 551.2010(557.2007) | 3244, 3115, 2978, 1704, 1642, 1597, 1500, 1448, |
1231, 1089, 876, 758, 656 | |||||
6f | White solid | 87 | 179—181 | 591.1608(591.1617) | 3245, 3117, 2977, 1704, 1644, 1602, 1487, 1453, |
1375, 1322, 1231, 1091, 763 | |||||
6g | White solid | 86 | 161—162 | 591.1603(591.1617) | 3243, 3117, 2976, 1703, 1644, 1594, 1479, 1319, |
1231, 1092, 917, 761, 659 | |||||
6h | Pale yellow solid | 83 | 242—244 | 625.1904(625.1881) | 3247, 3123, 2979, 1705, 1646, 1599, 1498, 1433, |
1316, 1235, 1164, 1093, 1046, 923, 763, 663 | |||||
6i | Pale yellow solid | 83 | 287—289 | 497.1811(497.1795) | 3228, 3116, 2927, 1692, 1646, 1598, 1499, 1460, |
1230, 871, 790 | |||||
6j | Pale yellow solid | 83 | 197—199 | 531.1419(531.1406) | 3235, 3231, 2928, 1693, 1642, 1603, 1488, 1432, |
1379, 1327, 1243, 1112, 815 | |||||
6k | White solid | 85 | 193—195 | 531.1410(531.1406) | 3241, 3234, 2956, 1704, 1644, 1595, 1478, 1320, |
1235, 1109, 918, 766, 659 | |||||
6l | White solid | 80 | 186—188 | 565.1689(565.1669) | 3238, 3131, 2929, 1704, 1648, 1600, 1497, 1385, |
1316, 1238, 1162, 1120, 1043, 924, 763, 714 |
Table 2 Appearance, yields, melting points, HRMS data and IR data for compounds 6a—6l
Compd. | Appearance | Yield(%) | m.p./℃ | HRMS(ESI)[M+Na]+ (calcd.), m/z | IR(KBr), /cm-1 |
---|---|---|---|---|---|
6a | Pale yellow solid | 86 | 182—184 | 529.1690(529.1694) | 3236, 3120, 2949, 1702, 1642, 1602, 1500, 1434, |
1232, 1090, 875, 758, 655 | |||||
6b | White solid | 85 | 185—187 | 563.1295(563.1304) | 3248, 2950, 1702, 1645, 1604, 1488, 1434, 1384, |
1319, 1231, 1092, 757 | |||||
6c | White solid | 84 | 189—190 | 563.1296(563.1304) | 3242, 3116, 2950, 1704, 1644, 1593, 1480, 1319, |
1232, 1092, 917, 761, 659 | |||||
6d | Pale yellow solid | 81 | 171—173 | 597.1591(597.1568) | 3247, 2952, 1705, 1644, 1601, 1497, 1432, 1316, |
1235, 1162, 1093, 923, 763, 662 | |||||
6e | Pale yellow solid | 84 | 163—164 | 551.2010(557.2007) | 3244, 3115, 2978, 1704, 1642, 1597, 1500, 1448, |
1231, 1089, 876, 758, 656 | |||||
6f | White solid | 87 | 179—181 | 591.1608(591.1617) | 3245, 3117, 2977, 1704, 1644, 1602, 1487, 1453, |
1375, 1322, 1231, 1091, 763 | |||||
6g | White solid | 86 | 161—162 | 591.1603(591.1617) | 3243, 3117, 2976, 1703, 1644, 1594, 1479, 1319, |
1231, 1092, 917, 761, 659 | |||||
6h | Pale yellow solid | 83 | 242—244 | 625.1904(625.1881) | 3247, 3123, 2979, 1705, 1646, 1599, 1498, 1433, |
1316, 1235, 1164, 1093, 1046, 923, 763, 663 | |||||
6i | Pale yellow solid | 83 | 287—289 | 497.1811(497.1795) | 3228, 3116, 2927, 1692, 1646, 1598, 1499, 1460, |
1230, 871, 790 | |||||
6j | Pale yellow solid | 83 | 197—199 | 531.1419(531.1406) | 3235, 3231, 2928, 1693, 1642, 1603, 1488, 1432, |
1379, 1327, 1243, 1112, 815 | |||||
6k | White solid | 85 | 193—195 | 531.1410(531.1406) | 3241, 3234, 2956, 1704, 1644, 1595, 1478, 1320, |
1235, 1109, 918, 766, 659 | |||||
6l | White solid | 80 | 186—188 | 565.1689(565.1669) | 3238, 3131, 2929, 1704, 1648, 1600, 1497, 1385, |
1316, 1238, 1162, 1120, 1043, 924, 763, 714 |
Compd. | 1H NMR(400 MHz, DMSO-d6), δ | 13C NMR(100 MHz, DMSO-d6), δ |
---|---|---|
6a | 9.28(s, 2H, NH), 7.81(s, 2H, NH), 7.25(d, J=7.2 Hz, 4H, ArH), 6.96(d, J=7.2 Hz, 4H, ArH), 5.17(s, 2H), 3.54(s, 6H), 2.28(s, 6H) | 165.85, 155.76, 152.24, 148.69, 139.82, 127.93, 118.52, 99.08, 53.29, 50.84, 17.90 |
6b | 9.33(s, 1H, NH), 9.25(s, 1H, NH), 7.84(s, 1H, NH), 7.77(s, 1H, NH), 7.39(d, J=1.6 Hz, 1H, ArH), 7.23(d, J=8.4 Hz, 2H ArH), 7.20(dd, J=1.6, 8.4 Hz, 1H, ArH), 7.06(d, J=8.0 Hz, 1H, ArH), 6.90(d, J=8.0 Hz, 2H, ArH), 5.17(d, J=3.2 Hz, 1H), 5.13(d, J=3.2 Hz, 1H), 3.56(s, 3H), 3.54(s, 3H), 2.27(s, 3H), 2.25(s, 3H) | 165.76, 165.68, 155.53, 152.08, 151.92, 150.46, 149.28, 148.69, 141.97, 139.84, 128.32, 127.93, 126.51, 124.32, 121.18, 117.28, 98.93, 98.32, 53.16, 52.91, 50.92, 50.81, 17.90, 17.83 |
6c | 9.35(s, 1H, NH), 9.29(s, 1H, NH), 7.82(s, 1H, NH), 7.74(s, 1H, NH), 7.03(d, J=6.8 Hz, 2H, ArH), 6.99(s, 1H, ArH), 6.95(d, J=7.6 Hz, 1H, ArH), 6.90—7.20(m, 3H, ArH), 5.59(s, 1H), 5.18(s, 1H), 3.55(s, 3H), 3.48(s, 3H), 2.30(s, 3H), 2.27(s, 3H) | 165.83, 165.50, 156.71, 154.76, 152.22, 151.57, 149.45, 148.75, 140.71, 136.39, 132.49, 130.00, 128.12, 119.28, 118.51, 117.46, 99.01, 97.79, 53.33, 50.96, 50.83, 50.78, 17.91, 17.80 |
6d | 9.40(s, 1H, NH), 9.28(s, 1H, NH), 7.81(s, 1H, NH), 7.51(s, 1H, NH), 7.22—7.44(m, 5H, ArH), 7.06(d, J=6.0 Hz, 2H, ArH), 5.53(s, 1H), 5.18(s, 1H), 3.55(s, 3H), 3.44(s, 3H), 2.33(s, 3H), 2.27(s, 3H) | 165.98, 165.41, 156.34, 154.70, 152.32, 151.36, 149.90, 148.97, 141.06, 137.96, 131.13, 128.35, 127.43(q, 2JCCF =29 Hz), 125.53, 122.42, 115.05, 120.92(q, 1JCF =263 Hz), 99.11, 98.33, 53.45, 51.00, 50.80, 50.18, 18.06, 17.93 |
6e | 9.28(s, 2H, NH), 7.80(s, 2H, NH), 7.28(d, J=8.4 Hz, 4H, ArH), 6.97(d, J=8.3 Hz, 4H, ArH), 5.20(s, 2H), 4.00(m, 4H), 2.29(s, 6H), 1.10(t, J=8.0 Hz, 6H) | 165.36, 155.81, 152.26, 148.37, 140.06, 128.04, 118.47, 99.37, 59.28, 53.53, 17.86, 14.10 |
6f | 9.29(s, 1H, NH), 9.21(s, 1H, NH), 7.81(s, 1H, NH), 7.74(s, 1H, NH), 7.39(s, 1H, ArH), 7.18—7.30(m, 3H, ArH), 7.07(d, J=8.4 Hz, 1H, ArH), 6.90(d, J=8.4 Hz, 2H, ArH), 5.17(d, J=3.2 Hz, 1H), 5.14(d, J =3.2 Hz, 1H), 4.01(m, 4H), 2.27(s, 3H), 2.25(s, 3H), 1.10(t, J=6.4 Hz, 3H), 1.09(t, J=6.8 Hz, 3H) | 165.26, 165.14, 155.54, 152.02, 151.85, 150.40, 148.95, 148.36, 142.25, 140.03, 128.47, 128.00, 126.58, 124.23, 121.19, 117.16, 99.17, 98.55, 59.29, 59.19, 53.35, 53.14, 17.83, 17.77, 14.05, 13.92 |
6g | 9.31(s, 1H, NH), 9.26(s, 1H, NH), 7.79(s, 1H, NH), 7.73(s, 1H, NH), 7.24—7.40(m, 3H, ArH), 6.90—7.08(m, 4H, ArH), 5.61(s, 1H), 5.19(s, 1H), 4.00(q, J=7.6 Hz, 2H), 3.94(q, J=6.8 Hz, 2H), 2.32(s, 3H), 2.25(s, 3H), 1.09(t, J=6.8 Hz, 3H), 1.02(t, J=6.8 Hz, 3H) | 165.32, 164.98, 156.72, 154.79, 152.13, 151.47, 149.25, 148.46, 140.94, 136.61, 132.51, 130.13, 128.23, 119.19, 118.35, 117.51, 99.22, 97.94, 59.25, 59.16, 53.54, 51.07, 17.83, 17.71, 14.09, 13.96 |
6h | 9.36(s, 1H, NH), 9.23(s, 1H, NH), 7.77(s, 1H, NH), 7.70(s, 1H, NH), 7.49(d, J=8.4 Hz, 1H, ArH), 7.30(m, 4H, ArH), 7.19(s, 1H, ArH), 7.04(d, J=8.4 Hz, 1H, ArH), 5.53(s, 1H), 5.16(s, 1H), 3.99(q, J=7.2 Hz, 2H), 3.88(q, J=6.8 Hz, 2H), 2.31(s, 3H), 2.28(s, 3H), 1.09(t, J=6.8 Hz, 3H), 0.92(t, J=6.8 Hz, 3H) | 165.46, 164.92, 156.41, 154.74, 152.27, 151.36, 149.86, 148.67, 141.29, 137.83, 131.08, 128.48, 127.56(q, 2JCCF=31 Hz), 125.18, 122.67, 121.09(q, 1JCF=273 Hz), 114.95, 99.32, 98.31, 59.38, 59.31, 53.72, 50.23, 17.98, 17.91, 14.20, 13.95 |
6i | 9.21(s, 2H, NH), 7.84(s, 2H, NH), 7.25(d, J=7.2 Hz, 4H, ArH), 6.96(d, J=7.2 Hz, 4H, ArH), 5.25(s, 2H), 2.29(s, 6H), 2.11(s, 6H) | 194.21, 155.71, 152.03, 148.11, 139.32, 128.11, 118.50, 109.52, 53.18, 30.31, 18.90 |
6j | 9.28(s,1H, NH), 9.21(s, 1H, NH), 7.90(s, 1H, NH), 7.84(s, 1H, NH), 7.41(s, 1H, ArH), 7.24(d, J=8.4 Hz, 2H, ArH), 7.19(dd, J=1.6, 8.4 Hz, 1H, ArH), 7.05(d, J=8.4 Hz, 1H, ArH), 6.90(d, J=8.4 Hz, 2H), 5.27(d, J=3.2 Hz, 1H), 5.24(d, J=3.2 Hz, 1H), 2.34(s, 3H), 2.29(s, 3H), 2.12(s, 3H), 2.07(s, 3H) | 194.17, 194.10, 155.57, 152.00, 151.96, 150.43, 148.72, 148.12, 141.61, 139.36, 128.54, 128.16, 126.62, 124.36, 121.18, 117.29, 109.51, 109.26, 53.13, 52.70, 30.48, 30.31, 18.99, 18.88 |
6k | 9.28(s, 1H, NH), 9.22(s, 1H, NH), 7.85(s, 1H, NH), 7.74(s, 1H, NH), 7.28(d, J=8.4 Hz, 2H, ArH), 7.24(d, J=8.4 Hz, 1H, ArH), 7.04(s, 1H, ArH), 7.02(d, J=2.8 Hz, 2H, ArH), 6.93(dd, J=1.6, 8.4 Hz, 1H, ArH), 5.61(d, J=3.2 Hz, 1H), 5.26(d, J=3.2Hz, 1H), 2.34(s, 3H), 2.29(s, 3H), 2.12(s, 3H), 2.07(s, 3H) | 194.15, 193.86, 156.78, 154.64, 151.98, 151.43, 148.72, 148.15, 140.23, 135.58, 132.51, 129.75, 128.25, 119.27, 118.52, 117.38, 109.51, 108.34, 53.13, 50.92, 30.31, 30.07, 18.88, 18.80 |
6l | 9.34(s, 1H, NH), 9.22(s, 1H, NH), 7.87(s, 1H, NH), 7.73(s, 1H, NH), 7.42(d, J=8 Hz, 1H, ArH), 7.20—7.32(m, 4H, ArH), 7.06(d, J=8.8 Hz, 2H, ArH), 5.57(d, J=2.8 Hz, 1H), 5.27(d, J=3.2 Hz, 1H), 2.34(s, 3H), 2.29(s, 3H), 2.12(s, 3H), 2.07(s, 3H) | 194.30, 193.88, 156.36, 154.55, 152.16, 151.36, 148.86, 148.35, 140.51, 136.88, 130.82, 128.46, 127.62(q, 2JCCF=31 Hz), 125.09, 120.83(q, 1JCF=277 Hz), 120.56, 115.28, 109.09, 108.72, 53.38, 50.38, 30.56, 30.42, 19.05, 19.01 |
Table 3 1H NMR and 13C NMR data for compounds 6a—6l
Compd. | 1H NMR(400 MHz, DMSO-d6), δ | 13C NMR(100 MHz, DMSO-d6), δ |
---|---|---|
6a | 9.28(s, 2H, NH), 7.81(s, 2H, NH), 7.25(d, J=7.2 Hz, 4H, ArH), 6.96(d, J=7.2 Hz, 4H, ArH), 5.17(s, 2H), 3.54(s, 6H), 2.28(s, 6H) | 165.85, 155.76, 152.24, 148.69, 139.82, 127.93, 118.52, 99.08, 53.29, 50.84, 17.90 |
6b | 9.33(s, 1H, NH), 9.25(s, 1H, NH), 7.84(s, 1H, NH), 7.77(s, 1H, NH), 7.39(d, J=1.6 Hz, 1H, ArH), 7.23(d, J=8.4 Hz, 2H ArH), 7.20(dd, J=1.6, 8.4 Hz, 1H, ArH), 7.06(d, J=8.0 Hz, 1H, ArH), 6.90(d, J=8.0 Hz, 2H, ArH), 5.17(d, J=3.2 Hz, 1H), 5.13(d, J=3.2 Hz, 1H), 3.56(s, 3H), 3.54(s, 3H), 2.27(s, 3H), 2.25(s, 3H) | 165.76, 165.68, 155.53, 152.08, 151.92, 150.46, 149.28, 148.69, 141.97, 139.84, 128.32, 127.93, 126.51, 124.32, 121.18, 117.28, 98.93, 98.32, 53.16, 52.91, 50.92, 50.81, 17.90, 17.83 |
6c | 9.35(s, 1H, NH), 9.29(s, 1H, NH), 7.82(s, 1H, NH), 7.74(s, 1H, NH), 7.03(d, J=6.8 Hz, 2H, ArH), 6.99(s, 1H, ArH), 6.95(d, J=7.6 Hz, 1H, ArH), 6.90—7.20(m, 3H, ArH), 5.59(s, 1H), 5.18(s, 1H), 3.55(s, 3H), 3.48(s, 3H), 2.30(s, 3H), 2.27(s, 3H) | 165.83, 165.50, 156.71, 154.76, 152.22, 151.57, 149.45, 148.75, 140.71, 136.39, 132.49, 130.00, 128.12, 119.28, 118.51, 117.46, 99.01, 97.79, 53.33, 50.96, 50.83, 50.78, 17.91, 17.80 |
6d | 9.40(s, 1H, NH), 9.28(s, 1H, NH), 7.81(s, 1H, NH), 7.51(s, 1H, NH), 7.22—7.44(m, 5H, ArH), 7.06(d, J=6.0 Hz, 2H, ArH), 5.53(s, 1H), 5.18(s, 1H), 3.55(s, 3H), 3.44(s, 3H), 2.33(s, 3H), 2.27(s, 3H) | 165.98, 165.41, 156.34, 154.70, 152.32, 151.36, 149.90, 148.97, 141.06, 137.96, 131.13, 128.35, 127.43(q, 2JCCF =29 Hz), 125.53, 122.42, 115.05, 120.92(q, 1JCF =263 Hz), 99.11, 98.33, 53.45, 51.00, 50.80, 50.18, 18.06, 17.93 |
6e | 9.28(s, 2H, NH), 7.80(s, 2H, NH), 7.28(d, J=8.4 Hz, 4H, ArH), 6.97(d, J=8.3 Hz, 4H, ArH), 5.20(s, 2H), 4.00(m, 4H), 2.29(s, 6H), 1.10(t, J=8.0 Hz, 6H) | 165.36, 155.81, 152.26, 148.37, 140.06, 128.04, 118.47, 99.37, 59.28, 53.53, 17.86, 14.10 |
6f | 9.29(s, 1H, NH), 9.21(s, 1H, NH), 7.81(s, 1H, NH), 7.74(s, 1H, NH), 7.39(s, 1H, ArH), 7.18—7.30(m, 3H, ArH), 7.07(d, J=8.4 Hz, 1H, ArH), 6.90(d, J=8.4 Hz, 2H, ArH), 5.17(d, J=3.2 Hz, 1H), 5.14(d, J =3.2 Hz, 1H), 4.01(m, 4H), 2.27(s, 3H), 2.25(s, 3H), 1.10(t, J=6.4 Hz, 3H), 1.09(t, J=6.8 Hz, 3H) | 165.26, 165.14, 155.54, 152.02, 151.85, 150.40, 148.95, 148.36, 142.25, 140.03, 128.47, 128.00, 126.58, 124.23, 121.19, 117.16, 99.17, 98.55, 59.29, 59.19, 53.35, 53.14, 17.83, 17.77, 14.05, 13.92 |
6g | 9.31(s, 1H, NH), 9.26(s, 1H, NH), 7.79(s, 1H, NH), 7.73(s, 1H, NH), 7.24—7.40(m, 3H, ArH), 6.90—7.08(m, 4H, ArH), 5.61(s, 1H), 5.19(s, 1H), 4.00(q, J=7.6 Hz, 2H), 3.94(q, J=6.8 Hz, 2H), 2.32(s, 3H), 2.25(s, 3H), 1.09(t, J=6.8 Hz, 3H), 1.02(t, J=6.8 Hz, 3H) | 165.32, 164.98, 156.72, 154.79, 152.13, 151.47, 149.25, 148.46, 140.94, 136.61, 132.51, 130.13, 128.23, 119.19, 118.35, 117.51, 99.22, 97.94, 59.25, 59.16, 53.54, 51.07, 17.83, 17.71, 14.09, 13.96 |
6h | 9.36(s, 1H, NH), 9.23(s, 1H, NH), 7.77(s, 1H, NH), 7.70(s, 1H, NH), 7.49(d, J=8.4 Hz, 1H, ArH), 7.30(m, 4H, ArH), 7.19(s, 1H, ArH), 7.04(d, J=8.4 Hz, 1H, ArH), 5.53(s, 1H), 5.16(s, 1H), 3.99(q, J=7.2 Hz, 2H), 3.88(q, J=6.8 Hz, 2H), 2.31(s, 3H), 2.28(s, 3H), 1.09(t, J=6.8 Hz, 3H), 0.92(t, J=6.8 Hz, 3H) | 165.46, 164.92, 156.41, 154.74, 152.27, 151.36, 149.86, 148.67, 141.29, 137.83, 131.08, 128.48, 127.56(q, 2JCCF=31 Hz), 125.18, 122.67, 121.09(q, 1JCF=273 Hz), 114.95, 99.32, 98.31, 59.38, 59.31, 53.72, 50.23, 17.98, 17.91, 14.20, 13.95 |
6i | 9.21(s, 2H, NH), 7.84(s, 2H, NH), 7.25(d, J=7.2 Hz, 4H, ArH), 6.96(d, J=7.2 Hz, 4H, ArH), 5.25(s, 2H), 2.29(s, 6H), 2.11(s, 6H) | 194.21, 155.71, 152.03, 148.11, 139.32, 128.11, 118.50, 109.52, 53.18, 30.31, 18.90 |
6j | 9.28(s,1H, NH), 9.21(s, 1H, NH), 7.90(s, 1H, NH), 7.84(s, 1H, NH), 7.41(s, 1H, ArH), 7.24(d, J=8.4 Hz, 2H, ArH), 7.19(dd, J=1.6, 8.4 Hz, 1H, ArH), 7.05(d, J=8.4 Hz, 1H, ArH), 6.90(d, J=8.4 Hz, 2H), 5.27(d, J=3.2 Hz, 1H), 5.24(d, J=3.2 Hz, 1H), 2.34(s, 3H), 2.29(s, 3H), 2.12(s, 3H), 2.07(s, 3H) | 194.17, 194.10, 155.57, 152.00, 151.96, 150.43, 148.72, 148.12, 141.61, 139.36, 128.54, 128.16, 126.62, 124.36, 121.18, 117.29, 109.51, 109.26, 53.13, 52.70, 30.48, 30.31, 18.99, 18.88 |
6k | 9.28(s, 1H, NH), 9.22(s, 1H, NH), 7.85(s, 1H, NH), 7.74(s, 1H, NH), 7.28(d, J=8.4 Hz, 2H, ArH), 7.24(d, J=8.4 Hz, 1H, ArH), 7.04(s, 1H, ArH), 7.02(d, J=2.8 Hz, 2H, ArH), 6.93(dd, J=1.6, 8.4 Hz, 1H, ArH), 5.61(d, J=3.2 Hz, 1H), 5.26(d, J=3.2Hz, 1H), 2.34(s, 3H), 2.29(s, 3H), 2.12(s, 3H), 2.07(s, 3H) | 194.15, 193.86, 156.78, 154.64, 151.98, 151.43, 148.72, 148.15, 140.23, 135.58, 132.51, 129.75, 128.25, 119.27, 118.52, 117.38, 109.51, 108.34, 53.13, 50.92, 30.31, 30.07, 18.88, 18.80 |
6l | 9.34(s, 1H, NH), 9.22(s, 1H, NH), 7.87(s, 1H, NH), 7.73(s, 1H, NH), 7.42(d, J=8 Hz, 1H, ArH), 7.20—7.32(m, 4H, ArH), 7.06(d, J=8.8 Hz, 2H, ArH), 5.57(d, J=2.8 Hz, 1H), 5.27(d, J=3.2 Hz, 1H), 2.34(s, 3H), 2.29(s, 3H), 2.12(s, 3H), 2.07(s, 3H) | 194.30, 193.88, 156.36, 154.55, 152.16, 151.36, 148.86, 148.35, 140.51, 136.88, 130.82, 128.46, 127.62(q, 2JCCF=31 Hz), 125.09, 120.83(q, 1JCF=277 Hz), 120.56, 115.28, 109.09, 108.72, 53.38, 50.38, 30.56, 30.42, 19.05, 19.01 |
Entry | Timea/min | Solution color | Timeb/min | Yield(%) |
---|---|---|---|---|
1 | 0 | Colorless transparent | 600 | 40 |
2 | 10 | Pink | 60 | 85 |
3 | 20 | Blush | 52 | 87 |
4 | 30 | Red brown | 35 | 91 |
5 | 40 | Red brown | 15 | 95 |
6 | 40 | Red brown | 600 | 67 |
Table 4 Synthesis of 4, 4'-dimethyl acyl diphenyl ether
Entry | Timea/min | Solution color | Timeb/min | Yield(%) |
---|---|---|---|---|
1 | 0 | Colorless transparent | 600 | 40 |
2 | 10 | Pink | 60 | 85 |
3 | 20 | Blush | 52 | 87 |
4 | 30 | Red brown | 35 | 91 |
5 | 40 | Red brown | 15 | 95 |
6 | 40 | Red brown | 600 | 67 |
Entry | n(4a)∶n(3a)∶n(5)∶n(FeC13·6H2O) | Time/h | Yield(%) | |
---|---|---|---|---|
6a2 | 6a | |||
1 | 2∶1∶3∶0.12 | 3 | 10 | 78 |
2 | 2∶1∶3∶0.12 | 8 | 4 | 85 |
3 | 2.2∶1∶3∶0.12 | 3 | 5 | 86 |
4 | 1∶1∶1.5∶0.06 | 3 | 31 | 24 |
Table 5 Effects of feed ratios on the yields of compounds 6a2 and 6a
Entry | n(4a)∶n(3a)∶n(5)∶n(FeC13·6H2O) | Time/h | Yield(%) | |
---|---|---|---|---|
6a2 | 6a | |||
1 | 2∶1∶3∶0.12 | 3 | 10 | 78 |
2 | 2∶1∶3∶0.12 | 8 | 4 | 85 |
3 | 2.2∶1∶3∶0.12 | 3 | 5 | 86 |
4 | 1∶1∶1.5∶0.06 | 3 | 31 | 24 |
Compd. | R1 | R2 | R3 | Time/h | Yield(%) |
---|---|---|---|---|---|
6a | H | H | OMe | 3 | 86 |
6b | Cl | H | OMe | 3 | 85 |
6c | H | Cl | OMe | 4.5 | 84 |
6d | H | CF3 | OMe | 5.5 | 81 |
6e | H | H | OEt | 3 | 84 |
6f | Cl | H | OEt | 3 | 87 |
6g | H | Cl | OEt | 4.5 | 86 |
6h | H | CF3 | OEt | 5.5 | 83 |
6i | H | H | Me | 3 | 83 |
6j | Cl | H | Me | 3 | 83 |
6k | H | Cl | Me | 4.5 | 85 |
6l | H | CF3 | Me | 5.5 | 80 |
Table 6 Synthesis of dipyrimidinone diphenyl ethers
Compd. | R1 | R2 | R3 | Time/h | Yield(%) |
---|---|---|---|---|---|
6a | H | H | OMe | 3 | 86 |
6b | Cl | H | OMe | 3 | 85 |
6c | H | Cl | OMe | 4.5 | 84 |
6d | H | CF3 | OMe | 5.5 | 81 |
6e | H | H | OEt | 3 | 84 |
6f | Cl | H | OEt | 3 | 87 |
6g | H | Cl | OEt | 4.5 | 86 |
6h | H | CF3 | OEt | 5.5 | 83 |
6i | H | H | Me | 3 | 83 |
6j | Cl | H | Me | 3 | 83 |
6k | H | Cl | Me | 4.5 | 85 |
6l | H | CF3 | Me | 5.5 | 80 |
Compd. | Pathogenb | Toxicity regression equation | Correlation coefficient, r | EC50/(g·L-1) | EC95/(g·L-1) |
---|---|---|---|---|---|
6a | G.N. | y=1.3312+0.3291x | 0.9652 | 3.98 | #c |
G.S. | y=3.4131+1.5464x | 0.9602 | 0.01 | 0.13 | |
F.O. | y=2.8788+0.6988x | 0.9392 | 1.00 | 251.20 | |
P.S. | y=0.5433+1.8350x | 0.9662 | 0.25 | 2.50 | |
6b | G.N. | y=3.4131+0.2752x | 0.6781 | 501.15 | # |
G.S. | y=2.6531+0.6528x | 0.9910 | 1000.00 | # | |
F.O. | y=3.6758+0.2230x | 0.6148 | # | # | |
P.S. | y=3.2803+0.6096x | 0.9970 | 0.63 | 316.23 | |
6c | G.N. | y=4.0712+0.1222x | 0.9121 | # | # |
G.S. | y=1.0942+1.1763x | 0.8896 | 2.00 | 50.12 | |
F.O. | y=3.5800+0.2689x | 0.9543 | 199.53 | # | |
P.S. | y=3.2803+0.6096x | 0.8669 | 0.32 | 10 | |
6d | G.N. | y=-1.1359+2.7360x | 0.7946 | 0.173 | 0.30 |
G.S. | y=1.3077+1.1289x | 0.9049 | 2.00 | 50.12 | |
F.O. | y=2.1089+1.1040x | 0.9301 | 0.40 | 12.60 | |
P.S. | y=1.9894+0.7687x | 0.9307 | 10 | 998.96 | |
6e | G.N. | y=3.5061+0.3546x | 0.8316 | 15.85 | # |
G.S. | y=3.0687+0.4039x | 0.9018 | 50.10 | # | |
F.O. | y=3.2232+0.3822x | 0.8921 | 39.81 | # | |
P.S. | y=3.1676+0.2895x | 0.8792 | # | # | |
6f | G.N. | y=3.8165+0.2220x | 0.9176 | 199.53 | # |
G.S. | y=2.2142+0.7318x | 0.9434 | 6.31 | 1000.00 | |
F.O. | y=2.7895+0.5237x | 0.9306 | 15.85 | # | |
P.S. | y=0.0740+2.0495x | 0.9242 | 0.25 | 1.58 | |
6g | G.N. | y=4.6351+0.1662x | 0.9751 | 0.16 | # |
G.S. | y=3.1965+0.4804x | 0.9809 | 5.01 | # | |
F.O. | y=3.5263+0.5886x | 0.9793 | 0.32 | 199.53 | |
P.S. | y=4.3962+0.2753x | 0.7589 | 0.16 | # | |
6h | G.N. | y=3.6725+0.5530x | 0.9160 | 0.25 | 251.19 |
G.S. | y=2.7842+0.8036x | 0.9880 | 0.50 | 63.10 | |
F.O. | y=3.0753+1.0534x | 0.8231 | 0.06 | 2.24 | |
P.S. | y=3.6757+0.2454x | 0.7667 | 251.18 | # | |
6i | G.N. | y=4.3979+0.3552x | 0.9425 | 0.05 | # |
G.S. | y=3.5520+0.3234x | 0.7359 | 31.62 | # | |
F.O. | y=3.7541+0.6989x | 0.9989 | 0.06 | 12.59 | |
P.S. | y=0.6629+0.9838x | 0.9304 | 0.25 | 10 | |
6j | G.N. | y=4.3323+0.6308x | 0.9093 | 0.01 | 3.99 |
G.S. | y=4.5905+0.1394x | 0.9083 | 1.00 | # | |
F.O. | y=4.4752+0.2969x | 0.8913 | 0.06 | # | |
P.S. | y=4.4752+0.2969x | 0.9923 | 0.05 | 39.81 | |
6k | G.N. | y=3.4210+0.6748x | 0.8835 | 0.20 | 63.10 |
G.S. | y=0.2377+1.7920x | 0.9466 | 0.50 | 4.00 | |
F.O. | y=3.4654+0.5955x | 0.9858 | 0.40 | 199.53 | |
P.S. | y=3.4143+0.5568x | 0.9823 | 0.63 | 630.96 | |
6l | G.N. | y=4.0689+0.3160x | 0.9789 | 1.00 | # |
G.S. | y=0.2812+1.8047x | 0.9242 | 0.40 | 3.16 | |
F.O. | y=3.2386+0.5940x | 0.9932 | 0.80 | 501.18 | |
6l | P.S. | y=3.0429+0.7268x | 0.9070 | 0.50 | 100 |
Control | G.N. | y=2.2516+1.3367x | 0.9606 | 0.11 | 1.93 |
G.S. | y=5.6200+0.3975x | 0.9820 | 0.01 | 0.38 | |
F.O. | y=4.1679+0.5760x | 0.9542 | 0.03 | 19.97 | |
P.S. | y=4.4196+0.5095x | 0.9965 | 0.01 | 2.43 |
Table 7 Biological test results of compounds 6 to four vegetable pathogensa
Compd. | Pathogenb | Toxicity regression equation | Correlation coefficient, r | EC50/(g·L-1) | EC95/(g·L-1) |
---|---|---|---|---|---|
6a | G.N. | y=1.3312+0.3291x | 0.9652 | 3.98 | #c |
G.S. | y=3.4131+1.5464x | 0.9602 | 0.01 | 0.13 | |
F.O. | y=2.8788+0.6988x | 0.9392 | 1.00 | 251.20 | |
P.S. | y=0.5433+1.8350x | 0.9662 | 0.25 | 2.50 | |
6b | G.N. | y=3.4131+0.2752x | 0.6781 | 501.15 | # |
G.S. | y=2.6531+0.6528x | 0.9910 | 1000.00 | # | |
F.O. | y=3.6758+0.2230x | 0.6148 | # | # | |
P.S. | y=3.2803+0.6096x | 0.9970 | 0.63 | 316.23 | |
6c | G.N. | y=4.0712+0.1222x | 0.9121 | # | # |
G.S. | y=1.0942+1.1763x | 0.8896 | 2.00 | 50.12 | |
F.O. | y=3.5800+0.2689x | 0.9543 | 199.53 | # | |
P.S. | y=3.2803+0.6096x | 0.8669 | 0.32 | 10 | |
6d | G.N. | y=-1.1359+2.7360x | 0.7946 | 0.173 | 0.30 |
G.S. | y=1.3077+1.1289x | 0.9049 | 2.00 | 50.12 | |
F.O. | y=2.1089+1.1040x | 0.9301 | 0.40 | 12.60 | |
P.S. | y=1.9894+0.7687x | 0.9307 | 10 | 998.96 | |
6e | G.N. | y=3.5061+0.3546x | 0.8316 | 15.85 | # |
G.S. | y=3.0687+0.4039x | 0.9018 | 50.10 | # | |
F.O. | y=3.2232+0.3822x | 0.8921 | 39.81 | # | |
P.S. | y=3.1676+0.2895x | 0.8792 | # | # | |
6f | G.N. | y=3.8165+0.2220x | 0.9176 | 199.53 | # |
G.S. | y=2.2142+0.7318x | 0.9434 | 6.31 | 1000.00 | |
F.O. | y=2.7895+0.5237x | 0.9306 | 15.85 | # | |
P.S. | y=0.0740+2.0495x | 0.9242 | 0.25 | 1.58 | |
6g | G.N. | y=4.6351+0.1662x | 0.9751 | 0.16 | # |
G.S. | y=3.1965+0.4804x | 0.9809 | 5.01 | # | |
F.O. | y=3.5263+0.5886x | 0.9793 | 0.32 | 199.53 | |
P.S. | y=4.3962+0.2753x | 0.7589 | 0.16 | # | |
6h | G.N. | y=3.6725+0.5530x | 0.9160 | 0.25 | 251.19 |
G.S. | y=2.7842+0.8036x | 0.9880 | 0.50 | 63.10 | |
F.O. | y=3.0753+1.0534x | 0.8231 | 0.06 | 2.24 | |
P.S. | y=3.6757+0.2454x | 0.7667 | 251.18 | # | |
6i | G.N. | y=4.3979+0.3552x | 0.9425 | 0.05 | # |
G.S. | y=3.5520+0.3234x | 0.7359 | 31.62 | # | |
F.O. | y=3.7541+0.6989x | 0.9989 | 0.06 | 12.59 | |
P.S. | y=0.6629+0.9838x | 0.9304 | 0.25 | 10 | |
6j | G.N. | y=4.3323+0.6308x | 0.9093 | 0.01 | 3.99 |
G.S. | y=4.5905+0.1394x | 0.9083 | 1.00 | # | |
F.O. | y=4.4752+0.2969x | 0.8913 | 0.06 | # | |
P.S. | y=4.4752+0.2969x | 0.9923 | 0.05 | 39.81 | |
6k | G.N. | y=3.4210+0.6748x | 0.8835 | 0.20 | 63.10 |
G.S. | y=0.2377+1.7920x | 0.9466 | 0.50 | 4.00 | |
F.O. | y=3.4654+0.5955x | 0.9858 | 0.40 | 199.53 | |
P.S. | y=3.4143+0.5568x | 0.9823 | 0.63 | 630.96 | |
6l | G.N. | y=4.0689+0.3160x | 0.9789 | 1.00 | # |
G.S. | y=0.2812+1.8047x | 0.9242 | 0.40 | 3.16 | |
F.O. | y=3.2386+0.5940x | 0.9932 | 0.80 | 501.18 | |
6l | P.S. | y=3.0429+0.7268x | 0.9070 | 0.50 | 100 |
Control | G.N. | y=2.2516+1.3367x | 0.9606 | 0.11 | 1.93 |
G.S. | y=5.6200+0.3975x | 0.9820 | 0.01 | 0.38 | |
F.O. | y=4.1679+0.5760x | 0.9542 | 0.03 | 19.97 | |
P.S. | y=4.4196+0.5095x | 0.9965 | 0.01 | 2.43 |
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