Efficient Synthesis of Pyridine ［2，3-d］pyrimidine Derivatives by Catalyst-free Tandem Cyclization Under Microwave Irradiation

doi:10.7503/cjcu20200563

Abstract

Abstract:

This work presents a highly efficient and simple method for the synthesis of pyridine ［2，3-d］ pyrimidine derivatives. This method took the α，β-unsaturated ketones compounds and 1，3-dimethyl-6-aminouracil as raw material， 28 pyridine ［2，3-d］pyrimidine derivatives were synthesized by microwave irradiation high-efficiency tandem cyclization in 5―15 min without catalyst， including 21 compounds did not see the literature. This method has the characteristics of simple and easy raw materials， high green efficiency， high bonding efficiency and simple post-treatment.

Key words: α, β-Unsaturated ketone, Pyridine ［2, 3-d］pyrimidine, Microwave irradiation, Catalyst-free, Tandem cyclization

CLC Number:

O621.3

TrendMD:

LIN Junjie, WANG Shuang, LI Weiqiang, CUI Xin, HUANG Chao. Efficient Synthesis of Pyridine ［2，3-d］pyrimidine Derivatives by Catalyst-free Tandem Cyclization Under Microwave Irradiation[J]. Chem. J. Chinese Universities, 2020, 41(12): 2749.

Figures/Tables 7

Compd.	Appearance	Yield^*(%)	m. p./℃(ref.)	HRMS, m/z[M+H]⁺	IR(KBr), $ν ?$ /cm^-1
3a	White solid	88	245—246(262—264)^[14]	344.1398	3067, 2906, 1705, 1663, 1555, 1420, 1363, 1004, 771, 701
3b	White solid	85	220—223	358.1557	3327, 2988, 1658, 1550, 1364, 1092, 821, 777, 698
3c	White solid	83	220—222	358.1555	3335, 2978, 1701, 1658, 1553, 1364, 1121, 747, 609
3d	Yellow solid	85	260—262	371.1711	3376, 2977, 1702, 1655, 1553, 1417, 1095, 747, 610
3e	White solid	79	231—233	358.1555	3284, 2980, 1704, 1657, 1364, 1095, 699, 608
3f	White solid	78	232—234	358.1557	3384, 2987, 1605, 1690, 1655, 1369, 1193, 812, 748
3g	White solid	81	214—216(217—219)^[14]	372.1713	3379, 2988, 1705, 1658, 1655, 1363, 1093, 802, 749
3h	White solid	78	253—254	374.1504	3356, 2976, 1655, 1551, 1416, 1367, 1243, 1178, 608, 569
3i	White solid	82	201—203	388.1661	3357, 2989, 1706, 1678, 1261, 1083, 800, 608
3j	White solid	81	228—231	404.1609	3354, 2968, 1704, 1654, 1600, 1089, 999, 787, 609
3k	White solid	80	241—243(259—260)^[14]	388.1661	3368, 2879, 1706, 1674, 1603, 1089, 998, 786, 605
3l	White solid	88	241—243	362.1306	3389, 2989, 1708, 1661, 1550, 1361, 1159, 1001, 608, 562
3m	White solid	85	251—253	378.1008	3354, 2968, 1655, 1567, 1365, 1094, 752, 609
3n	White solid	85	231—233	422.0505	3375, 2968, 1655, 1549, 1360, 1112, 1001, 751, 609
3o	White solid	84	235—237	376.1463	3389, 2988, 1666, 1567, 1546, 1153, 1096, 840, 799, 607
3p	White solid	84	232—233(238—239)^[14]	392.1167	3387, 2999, 1701, 1667, 1590, 1545, 1366, 1091, 799, 610
3q	White solid	82	230—232	436.0662	3375, 2976, 1705, 1592, 1543, 1361, 1086, 1003, 823, 750, 609
3r	Yellow solid	79	240—242	389.1252	3369, 2968, 1706, 1670, 1550, 1342, 1109, 521, 694, 609
3s	White solid	77	214—215	369.1351	3378, 2899, 2025, 1704, 1360, 1120, 608, 536
3t	White solid	78	215—217	360.1349	3397, 3066, 2948, 1710, 1670, 1551, 1367, 1224, 770, 746
3u	White solid	84	220—222	383.1509	3389, 2967, 1633, 1556, 1367, 1128, 999, 671
3v	Yellow solid	80	201—202	394.1555	3398, 2977, 1705, 1663, 1552, 1348, 1090, 767, 609
3w	Purple solid	81	238—240	350.0964	3386, 2988, 1709, 1656, 1415, 1097, 730, 607
3x	Yellow solid	81	217—218(213—215)^[33]	350.0965	3389, 2977, 2025, 1656, 1424, 1094, 800, 608
5a	White solid	70	165—166(171—178)^[12]	268.1083	3367, 2980, 1705, 1655, 1122, 608
5b	White solid	73	184—186	282.1235	3358, 2966, 1706, 1657, 1551, 1416, 1375, 754, 697, 550
5c	White solid	71	186—188	296.1941	3378, 2980, 2025, 1702, 1667, 2593, 1419, 753, 608
5d	White solid	78	185—186(180—182)^[12]	298.1193	3301, 3129, 2987, 1626, 1504, 1155, 1063, 754, 539

Compd.	Appearance	Yield^*(%)	m. p./℃(ref.)	HRMS, m/z[M+H]⁺	IR(KBr), $ν ?$ /cm^-1
3a	White solid	88	245—246(262—264)^[14]	344.1398	3067, 2906, 1705, 1663, 1555, 1420, 1363, 1004, 771, 701
3b	White solid	85	220—223	358.1557	3327, 2988, 1658, 1550, 1364, 1092, 821, 777, 698
3c	White solid	83	220—222	358.1555	3335, 2978, 1701, 1658, 1553, 1364, 1121, 747, 609
3d	Yellow solid	85	260—262	371.1711	3376, 2977, 1702, 1655, 1553, 1417, 1095, 747, 610
3e	White solid	79	231—233	358.1555	3284, 2980, 1704, 1657, 1364, 1095, 699, 608
3f	White solid	78	232—234	358.1557	3384, 2987, 1605, 1690, 1655, 1369, 1193, 812, 748
3g	White solid	81	214—216(217—219)^[14]	372.1713	3379, 2988, 1705, 1658, 1655, 1363, 1093, 802, 749
3h	White solid	78	253—254	374.1504	3356, 2976, 1655, 1551, 1416, 1367, 1243, 1178, 608, 569
3i	White solid	82	201—203	388.1661	3357, 2989, 1706, 1678, 1261, 1083, 800, 608
3j	White solid	81	228—231	404.1609	3354, 2968, 1704, 1654, 1600, 1089, 999, 787, 609
3k	White solid	80	241—243(259—260)^[14]	388.1661	3368, 2879, 1706, 1674, 1603, 1089, 998, 786, 605
3l	White solid	88	241—243	362.1306	3389, 2989, 1708, 1661, 1550, 1361, 1159, 1001, 608, 562
3m	White solid	85	251—253	378.1008	3354, 2968, 1655, 1567, 1365, 1094, 752, 609
3n	White solid	85	231—233	422.0505	3375, 2968, 1655, 1549, 1360, 1112, 1001, 751, 609
3o	White solid	84	235—237	376.1463	3389, 2988, 1666, 1567, 1546, 1153, 1096, 840, 799, 607
3p	White solid	84	232—233(238—239)^[14]	392.1167	3387, 2999, 1701, 1667, 1590, 1545, 1366, 1091, 799, 610
3q	White solid	82	230—232	436.0662	3375, 2976, 1705, 1592, 1543, 1361, 1086, 1003, 823, 750, 609
3r	Yellow solid	79	240—242	389.1252	3369, 2968, 1706, 1670, 1550, 1342, 1109, 521, 694, 609
3s	White solid	77	214—215	369.1351	3378, 2899, 2025, 1704, 1360, 1120, 608, 536
3t	White solid	78	215—217	360.1349	3397, 3066, 2948, 1710, 1670, 1551, 1367, 1224, 770, 746
3u	White solid	84	220—222	383.1509	3389, 2967, 1633, 1556, 1367, 1128, 999, 671
3v	Yellow solid	80	201—202	394.1555	3398, 2977, 1705, 1663, 1552, 1348, 1090, 767, 609
3w	Purple solid	81	238—240	350.0964	3386, 2988, 1709, 1656, 1415, 1097, 730, 607
3x	Yellow solid	81	217—218(213—215)^[33]	350.0965	3389, 2977, 2025, 1656, 1424, 1094, 800, 608
5a	White solid	70	165—166(171—178)^[12]	268.1083	3367, 2980, 1705, 1655, 1122, 608
5b	White solid	73	184—186	282.1235	3358, 2966, 1706, 1657, 1551, 1416, 1375, 754, 697, 550
5c	White solid	71	186—188	296.1941	3378, 2980, 2025, 1702, 1667, 2593, 1419, 753, 608
5d	White solid	78	185—186(180—182)^[12]	298.1193	3301, 3129, 2987, 1626, 1504, 1155, 1063, 754, 539

Compd.	¹H NMR(400 MHz), δ	¹³C NMR(100 MHz), δ
3a	8.13—8.15(m, 2H), 7.52—7.50(m, 3H), 7.48—7.46(m, 4H), 7.37—7.33(m, 2H), 3.89(s, 3H), 3.39(s, 3H)	159.5, 158.2, 154.2, 150.8, 150.6, 138.6, 136.2, 129.7, 127.9, 127.2, 126.8, 126.5, 117.4, 105.5, 29.1, 27.4
3b	8.25—8.28(s, 1H), 7.57—7.50(m, 3H), 7.30—7.28(m, 2H), 7.24—7.22(m, 2H), 3.72(s, 3H), 3.19(s, 3H), 2.38(s, 3H)	159.8, 157.7, 154.4, 151.5, 151.0, 137.2, 136.8, 136.4, 130.7, 129.0, 128.3, 128.0, 127.5, 117.8, 106.4, 99.5, 29.8, 28.0, 20.9
3c	8.18—8.16(s, 1H), 7.57(s, 1H), 7.43—7.33(m, 7H), 3.72(s, 3H), 3.19(s, 3H), 2.38(s, 3H)	159.5, 158.2, 154.1, 150.8, 150.6, 140.2, 138.7, 133.5, 128.7, 127.1, 126.8, 126.5, 117.0, 105.6, 29.1, 27.4, 20.4
3d	7.90—7,87 (m, 2H), 7.48—7.44(m, 4H), 7.36—7.34(m, 2H), 7.27(s, 1H), 3.89(s, 3H), 3.39(s, 3H), 2.37—2.34(m, 6H)	159.6, 158.4, 154.0, 150.7, 150.6, 138.9, 138.7, 136.2, 133.9, 129.3, 127.6, 127.1, 126.8, 126.8, 124.1, 117.1, 105.2, 29.1, 27.4, 19.0, 18.8
3e	8.23—8.26(m, 3H), 7.58(d,J=8.0 Hz, 1H), 7.52—7.53(m, 3H), 7.29—7.27(m, 2H), 3.71(s, 3H), 3.19(s, 3H), 2.38(s, 3H)	159.5, 158.1, 154.4, 150.8, 150.6, 137.1, 136.3, 135.6, 129.7, 127.9, 127.6, 126.8, 126.5, 117.5, 105.6, 29.1, 27.4, 20.0
3f	8.15—8.13(m, 2H), 7.52—7.50(m, 3H), 7.47(s, 1H), 7.30—7.24(m, 3H), 7.24(s, 1H), 3.89(s, 3H), 3.40(s, 3H), 2.44(s, 3H)	159.5, 158.1, 154.4, 150.8, 150.6, 137.1, 136.3, 135.6, 129.7, 127.9, 127.6, 126.8, 126.5, 117.5, 105.6, 29.1, 27.4, 20.4
3g	8.02—8.04(m, 2H), 7.44(s, 1H), 7.32—7.27(m, 5H), 7.25(d, J=6.1 Hz, 1H), 3.88(s, 3H), 3.39(s, 3H), 2.44(d, J=3.8 Hz, 6H)	159.6, 158.1, 154.2, 150.8, 150.6, 140.1, 137.0, 135.7, 133.5, 128.7, 127.8, 126.8, 126.4, 117.1, 105.3, 29.1, 27.4, 20.4, 20.4
3h	8.26(d, J=9.0 Hz, 2H), 7.56(s, 1H), 7.43—7.41(m, 5H), 7.08(d, J=9.0 Hz, 2H), 3.84(s, 3H), 3.73(s, 3H), 3.19(s, 3H)	160.9, 159.5, 157.8, 154.0 150.8, 150.6, 138.7, 128.7, 128.1, 127.1, 126.8, 126.8, 116.5, 113.3, 104.8, 54.4, 29.1, 27.4
3i	8.04(d, J=8.2 Hz, 2H), 7.43(s, 1H), 7.31(d, J=8.7 Hz, 4H), 7.00(d, J=8.8 Hz, 2H), 3.88(d, J=0.5 Hz, 6H), 3.40(s, 3H), 2.43(s, 3H)	159.7, 158.7, 158.1, 153.9, 150.9, 150.6, 140.1, 133.6, 130.7, 128.8, 128.4, 126.4, 117.3, 112.3, 105.2, 54.3, 29.1, 27.4, 20.4
3j	8.10(d, J=8.9 Hz, 2H), 8.10(d, J=8.9 Hz, 2H), 7.38(s, 1H), 7.30(d, J=8.7 Hz, 2H), 7.00(m, 4H), 3.88—3.86(m, 8H), 3.39(s, 3H)	160.9, 159.6, 158.7, 157.6, 153.8, 150.9, 150.6, 130.8, 128.8, 128.4, 128.0, 116.8, 113.3, 112.3, 104.8, 54.4, 54.3, 29.1, 27.4
3k	8.10(d, J=8.9 Hz, 2H), 7.39(s, 1H), 7.28(d, J=8.1 Hz, 2H), 7.25(m, 2H), 7.01(d, J=8.9 Hz, 2H), 3.88(d, J=7.4 Hz, 6H), 3.39(s, 3H), 2.44(s, 3H)	160.9, 159.6, 157.7, 154.1, 150.8, 150.6, 137.0, 135.8, 128.8, 128.0, 127.6, 126.8, 116.6, 113.3, 104.9, 54.4, 29.1, 27.4, 20.4
3l	8.17—8.13(m, 2H), 7.49—7.48(m, 3H), 7.42(s, 1H), 7.34(m, 2H), 7.19(t, J=8.7 Hz, 2H), 3.88(s, 3H), 3.39(s, 3H)	164.8, 162.3, 159.4, 157.1, 154.4, 150.8, 150.5, 138.5, 132.4, 132.4, 128.6, 128.5, 127.2, 126.9, 126.7, 117.0, 115.1, 114.9, 105.5, 29.1, 27.4
3m	8.09—8.07(m, 2H), 7.48—7.47(m, 5H), 7.46—7.44(s, 1H), 7.35—7.33(m, 2H), 3.87(s, 3H), 3.39(s, 3H)	159.4 156.9, 154.5, 150.8, 150.5, 138.4, 136.0, 134.7, 128.2, 127.8, 127.3, 126.9, 126.7, 117.1, 105.7, 29.2, 27.5
3n	8.02—8.00(m, 2H), 7.65—7.63(m, 2H), 7.48—7.47(m, 3H), 7.44(s, 1H), 7.35—7.33(m, 2H), 3.87(s, 3H), 3.39(s, 3H)	159.4, 157.0, 154.5, 150.8, 150.5, 138.4, 135.1, 131.2, 128.0, 127.3, 126.7, 126.7, 124.5, 117.1, 105.8, 29.2, 27.5
3o	8.16—8.12(m, 2H), 7.41(s, 1H), 7.28(d, J=8.1 Hz, 2H), 7.23—7.17(m, 4H), 3.87(s, 3H), 3.39(s, 3H), 2.44(s, 3H)	164.7, 162.2, 159.5, 157.0, 154.6, 150.8, 150.5, 137.2, 135.5, 132.5, 132.5, 128.6, 128.5, 127.6, 126.8, 117.1, 115.1, 114.9, 105.5, 29.1, 27.4, 20.4
Compd.	¹H NMR(400 MHz), δ	¹³C NMR(100 MHz), δ
3p	8.07(d, J=8.7 Hz, 2H), 7.47(d, J=8.7 Hz, 2H), 7.43(s, 1H), 7.28(d, J=8.0 Hz, 2H), 7.25—7.25(m, 2H), 3.87(s, 3H), 3.39(s, 3H), 2.44(s, 3H)	159.4, 156.8, 154.6, 150.9, 150.5, 137.2, 136.0, 135.4, 134.7, 128.2, 127.7, 127.6, 126.8, 117.2, 105.8, 29.2, 27.5, 20.4
3q	8.00(d, J=8.7 Hz, 2H), 7.63(d, J=8.7 Hz, 2H), 7.43(s, 1H), 7.28(d, J=8.0 Hz, 2H), 7.25—7.23(m, 2H), 3.87(s, 3H), 3.39(s, 3H), 2.44(s, 3H)	159.4, 156.9, 154.7, 150.9, 150.5, 137.2, 135.4, 135.2, 131.1, 128.0, 127.6, 126.8, 124.4, 117.2, 105.8, 29.2, 27.5, 20.4
3r	8.55(d, J=9.0 Hz, 2H), 8.34(d, J=9.0 Hz, 2H), 7.79(s, 1H), 7.45—7.41(m, 5H), 3.74(s, 3H), 3.20(s, 3H)	159.6, 155.3, 154.8, 151.6, 150.9, 148.5, 142.6, 139.1, 128.8, 128.3, 128.0, 127.5, 124.0, 119.0, 107.5, 29.9, 28.1
3s	8.26—8.24(m, 2H), 7.81—7.79(m, 2H), 7.50—7.46(m, 4H), 7.35—7.35(m, 2H), 3.88(s, 3H), 3.39(s, 3H)	159.2, 155.8, 154.9, 150.9, 150.3, 140.3, 138.1, 131.7, 127.5, 127.0, 127.0, 126.7, 117.8, 117.4, 113.0, 106.5, 29.2, 27.5
3t	13.20(s, 1H), 7.85—7.82(m, 1H), 7.57(s, 1H), 7.52—7.47(m, 1H), 7.44—7.38(m, 1H), 7.35(s, 1H), 7.07—7.05(m, 1H), 6.97—6.91(m, 1H), 3.82(s, 3H), 3.39(s, 3H)	159.2, 158.7, 154.8, 140.0, 139.4, 138.0, 132.6, 127.5, 127.0, 126.6, 118.6 117.8, 116.8, 116.4, 104.9, 29.5, 27.6
3u	8.25(d, J=8.4 Hz, 2H), 7.80(d, J=8.4 Hz, 2H), 7.50(s, 1H), 7.30—7.26(m, 2H), 7.24(s, 1H), 3.88(s, 3H), 3.40(s, 3H), 2.45(s, 3H)	159.2, 155.7, 155.1, 151.0, 150.4, 140.3, 137.5, 135.1, 131.7, 127.7, 127.0, 126.7, 118.0, 117.4, 113.0, 106.6, 29.2, 27.5, 20.4
3v	8.59(s, 1H), 8.27—8.25(m, 1H), 7.96—7.88(m, 3H), 7.62(s, 1H), 7.57—7.54(m, 2H), 7.51—7.49(m, 3H), 7.40—7.38(m, 2H), 3.93(s, 3H), 3.40(s, 3H)	159.5, 158.0, 154.2, 150.8, 150.5, 138.6, 133.5, 133.4, 132.2, 128.0, 127.7, 126.8, 126.7,126.7, 126.5, 125.6, 123.3, 117.5 105.5, 29.2, 27.4
3w	8.14—8.12(m, 2H), 7.60(s, 1H), 7.60—7.50(m, 4H), 7.26—7.24(m, 1H), 7.16—7.14(m, 1H), 3.87(s, 3H), 3.43(s, 3H)	159.3, 158.2, 151.0, 150.4, 146.71, 138.3, 136.0, 129.8, 127.9, 127.4, 126.5, 126.2, 125.9, 118.3, 105.7, 29.2, 27.5
3x	7.73—7.72(m, 1H), 7.56—7.54(m, 1H), 7.48—7.46(m, 3H), 7.35—7.33(m, 3H), 7.16—7.14(m, 1H), 3.83(s, 3H), 3.37(s, 3H)	159.3, 154.1, 153.3, 150.8, 150.5, 142.3, 138.4, 129.5, 127.5, 127.2, 126.8, 126.7, 126.4, 115.7, 105.1, 29.1, 27.4
5a	8.60(d, J=4.9 Hz, 1H), 7.46—7.44(m, 3H), 7.30—7.26(m, 2H), 7.01(d, J=4.9 Hz, 1H), 3.78(s, 3H), 3.37(s, 3H)	159.5, 153.5, 151.0, 150.3, 138.1, 127.2, 126.8, 121.0, 107.1, 29.2, 27.5
5b	7.44—7.42(m, 3H), 7.29—7.26(m, 2H), 6.87(s, 1H), 3.77(s, 3H), 3.36(s, 3H), 2.61(s, 3H)	161.6, 159.6, 153.4, 150.5, 138.4, 127.0, 126.7, 120.7, 104.5, 29.0, 27.3, 23.9
5c	7.25—7.23(m, 4H), 6.85(s, 1H), 3.76(s, 3H), 3.36(s, 3H), 2.60(s, 3H), 2.41(s, 3H)	161.5, 159.7, 153.6, 150.6, 150.6, 136.9, 135.4, 127.5, 126.7, 120.8, 104.6, 29.0, 27.4, 23.9, 20.3
5d	13.23(s, 1H), 7.52(s, 1H), 7.39—7.37(m, 1H), 7.04—7.02(m, 1H), 6.98—6.94(m, 1H), 3.74(s, 3H), 3.47(s, 3H), 2.91(s, 3H)	160.1, 159.1, 158.5, 153.7, 145.0, 149.3, 132.3, 126.3, 118.5, 117.7, 116.7, 116.2, 106.2, 29.4, 27.5, 22.1

Compd.	¹H NMR(400 MHz), δ	¹³C NMR(100 MHz), δ
3a	8.13—8.15(m, 2H), 7.52—7.50(m, 3H), 7.48—7.46(m, 4H), 7.37—7.33(m, 2H), 3.89(s, 3H), 3.39(s, 3H)	159.5, 158.2, 154.2, 150.8, 150.6, 138.6, 136.2, 129.7, 127.9, 127.2, 126.8, 126.5, 117.4, 105.5, 29.1, 27.4
3b	8.25—8.28(s, 1H), 7.57—7.50(m, 3H), 7.30—7.28(m, 2H), 7.24—7.22(m, 2H), 3.72(s, 3H), 3.19(s, 3H), 2.38(s, 3H)	159.8, 157.7, 154.4, 151.5, 151.0, 137.2, 136.8, 136.4, 130.7, 129.0, 128.3, 128.0, 127.5, 117.8, 106.4, 99.5, 29.8, 28.0, 20.9
3c	8.18—8.16(s, 1H), 7.57(s, 1H), 7.43—7.33(m, 7H), 3.72(s, 3H), 3.19(s, 3H), 2.38(s, 3H)	159.5, 158.2, 154.1, 150.8, 150.6, 140.2, 138.7, 133.5, 128.7, 127.1, 126.8, 126.5, 117.0, 105.6, 29.1, 27.4, 20.4
3d	7.90—7,87 (m, 2H), 7.48—7.44(m, 4H), 7.36—7.34(m, 2H), 7.27(s, 1H), 3.89(s, 3H), 3.39(s, 3H), 2.37—2.34(m, 6H)	159.6, 158.4, 154.0, 150.7, 150.6, 138.9, 138.7, 136.2, 133.9, 129.3, 127.6, 127.1, 126.8, 126.8, 124.1, 117.1, 105.2, 29.1, 27.4, 19.0, 18.8
3e	8.23—8.26(m, 3H), 7.58(d,J=8.0 Hz, 1H), 7.52—7.53(m, 3H), 7.29—7.27(m, 2H), 3.71(s, 3H), 3.19(s, 3H), 2.38(s, 3H)	159.5, 158.1, 154.4, 150.8, 150.6, 137.1, 136.3, 135.6, 129.7, 127.9, 127.6, 126.8, 126.5, 117.5, 105.6, 29.1, 27.4, 20.0
3f	8.15—8.13(m, 2H), 7.52—7.50(m, 3H), 7.47(s, 1H), 7.30—7.24(m, 3H), 7.24(s, 1H), 3.89(s, 3H), 3.40(s, 3H), 2.44(s, 3H)	159.5, 158.1, 154.4, 150.8, 150.6, 137.1, 136.3, 135.6, 129.7, 127.9, 127.6, 126.8, 126.5, 117.5, 105.6, 29.1, 27.4, 20.4
3g	8.02—8.04(m, 2H), 7.44(s, 1H), 7.32—7.27(m, 5H), 7.25(d, J=6.1 Hz, 1H), 3.88(s, 3H), 3.39(s, 3H), 2.44(d, J=3.8 Hz, 6H)	159.6, 158.1, 154.2, 150.8, 150.6, 140.1, 137.0, 135.7, 133.5, 128.7, 127.8, 126.8, 126.4, 117.1, 105.3, 29.1, 27.4, 20.4, 20.4
3h	8.26(d, J=9.0 Hz, 2H), 7.56(s, 1H), 7.43—7.41(m, 5H), 7.08(d, J=9.0 Hz, 2H), 3.84(s, 3H), 3.73(s, 3H), 3.19(s, 3H)	160.9, 159.5, 157.8, 154.0 150.8, 150.6, 138.7, 128.7, 128.1, 127.1, 126.8, 126.8, 116.5, 113.3, 104.8, 54.4, 29.1, 27.4
3i	8.04(d, J=8.2 Hz, 2H), 7.43(s, 1H), 7.31(d, J=8.7 Hz, 4H), 7.00(d, J=8.8 Hz, 2H), 3.88(d, J=0.5 Hz, 6H), 3.40(s, 3H), 2.43(s, 3H)	159.7, 158.7, 158.1, 153.9, 150.9, 150.6, 140.1, 133.6, 130.7, 128.8, 128.4, 126.4, 117.3, 112.3, 105.2, 54.3, 29.1, 27.4, 20.4
3j	8.10(d, J=8.9 Hz, 2H), 8.10(d, J=8.9 Hz, 2H), 7.38(s, 1H), 7.30(d, J=8.7 Hz, 2H), 7.00(m, 4H), 3.88—3.86(m, 8H), 3.39(s, 3H)	160.9, 159.6, 158.7, 157.6, 153.8, 150.9, 150.6, 130.8, 128.8, 128.4, 128.0, 116.8, 113.3, 112.3, 104.8, 54.4, 54.3, 29.1, 27.4
3k	8.10(d, J=8.9 Hz, 2H), 7.39(s, 1H), 7.28(d, J=8.1 Hz, 2H), 7.25(m, 2H), 7.01(d, J=8.9 Hz, 2H), 3.88(d, J=7.4 Hz, 6H), 3.39(s, 3H), 2.44(s, 3H)	160.9, 159.6, 157.7, 154.1, 150.8, 150.6, 137.0, 135.8, 128.8, 128.0, 127.6, 126.8, 116.6, 113.3, 104.9, 54.4, 29.1, 27.4, 20.4
3l	8.17—8.13(m, 2H), 7.49—7.48(m, 3H), 7.42(s, 1H), 7.34(m, 2H), 7.19(t, J=8.7 Hz, 2H), 3.88(s, 3H), 3.39(s, 3H)	164.8, 162.3, 159.4, 157.1, 154.4, 150.8, 150.5, 138.5, 132.4, 132.4, 128.6, 128.5, 127.2, 126.9, 126.7, 117.0, 115.1, 114.9, 105.5, 29.1, 27.4
3m	8.09—8.07(m, 2H), 7.48—7.47(m, 5H), 7.46—7.44(s, 1H), 7.35—7.33(m, 2H), 3.87(s, 3H), 3.39(s, 3H)	159.4 156.9, 154.5, 150.8, 150.5, 138.4, 136.0, 134.7, 128.2, 127.8, 127.3, 126.9, 126.7, 117.1, 105.7, 29.2, 27.5
3n	8.02—8.00(m, 2H), 7.65—7.63(m, 2H), 7.48—7.47(m, 3H), 7.44(s, 1H), 7.35—7.33(m, 2H), 3.87(s, 3H), 3.39(s, 3H)	159.4, 157.0, 154.5, 150.8, 150.5, 138.4, 135.1, 131.2, 128.0, 127.3, 126.7, 126.7, 124.5, 117.1, 105.8, 29.2, 27.5
3o	8.16—8.12(m, 2H), 7.41(s, 1H), 7.28(d, J=8.1 Hz, 2H), 7.23—7.17(m, 4H), 3.87(s, 3H), 3.39(s, 3H), 2.44(s, 3H)	164.7, 162.2, 159.5, 157.0, 154.6, 150.8, 150.5, 137.2, 135.5, 132.5, 132.5, 128.6, 128.5, 127.6, 126.8, 117.1, 115.1, 114.9, 105.5, 29.1, 27.4, 20.4
Compd.	¹H NMR(400 MHz), δ	¹³C NMR(100 MHz), δ
3p	8.07(d, J=8.7 Hz, 2H), 7.47(d, J=8.7 Hz, 2H), 7.43(s, 1H), 7.28(d, J=8.0 Hz, 2H), 7.25—7.25(m, 2H), 3.87(s, 3H), 3.39(s, 3H), 2.44(s, 3H)	159.4, 156.8, 154.6, 150.9, 150.5, 137.2, 136.0, 135.4, 134.7, 128.2, 127.7, 127.6, 126.8, 117.2, 105.8, 29.2, 27.5, 20.4
3q	8.00(d, J=8.7 Hz, 2H), 7.63(d, J=8.7 Hz, 2H), 7.43(s, 1H), 7.28(d, J=8.0 Hz, 2H), 7.25—7.23(m, 2H), 3.87(s, 3H), 3.39(s, 3H), 2.44(s, 3H)	159.4, 156.9, 154.7, 150.9, 150.5, 137.2, 135.4, 135.2, 131.1, 128.0, 127.6, 126.8, 124.4, 117.2, 105.8, 29.2, 27.5, 20.4
3r	8.55(d, J=9.0 Hz, 2H), 8.34(d, J=9.0 Hz, 2H), 7.79(s, 1H), 7.45—7.41(m, 5H), 3.74(s, 3H), 3.20(s, 3H)	159.6, 155.3, 154.8, 151.6, 150.9, 148.5, 142.6, 139.1, 128.8, 128.3, 128.0, 127.5, 124.0, 119.0, 107.5, 29.9, 28.1
3s	8.26—8.24(m, 2H), 7.81—7.79(m, 2H), 7.50—7.46(m, 4H), 7.35—7.35(m, 2H), 3.88(s, 3H), 3.39(s, 3H)	159.2, 155.8, 154.9, 150.9, 150.3, 140.3, 138.1, 131.7, 127.5, 127.0, 127.0, 126.7, 117.8, 117.4, 113.0, 106.5, 29.2, 27.5
3t	13.20(s, 1H), 7.85—7.82(m, 1H), 7.57(s, 1H), 7.52—7.47(m, 1H), 7.44—7.38(m, 1H), 7.35(s, 1H), 7.07—7.05(m, 1H), 6.97—6.91(m, 1H), 3.82(s, 3H), 3.39(s, 3H)	159.2, 158.7, 154.8, 140.0, 139.4, 138.0, 132.6, 127.5, 127.0, 126.6, 118.6 117.8, 116.8, 116.4, 104.9, 29.5, 27.6
3u	8.25(d, J=8.4 Hz, 2H), 7.80(d, J=8.4 Hz, 2H), 7.50(s, 1H), 7.30—7.26(m, 2H), 7.24(s, 1H), 3.88(s, 3H), 3.40(s, 3H), 2.45(s, 3H)	159.2, 155.7, 155.1, 151.0, 150.4, 140.3, 137.5, 135.1, 131.7, 127.7, 127.0, 126.7, 118.0, 117.4, 113.0, 106.6, 29.2, 27.5, 20.4
3v	8.59(s, 1H), 8.27—8.25(m, 1H), 7.96—7.88(m, 3H), 7.62(s, 1H), 7.57—7.54(m, 2H), 7.51—7.49(m, 3H), 7.40—7.38(m, 2H), 3.93(s, 3H), 3.40(s, 3H)	159.5, 158.0, 154.2, 150.8, 150.5, 138.6, 133.5, 133.4, 132.2, 128.0, 127.7, 126.8, 126.7,126.7, 126.5, 125.6, 123.3, 117.5 105.5, 29.2, 27.4
3w	8.14—8.12(m, 2H), 7.60(s, 1H), 7.60—7.50(m, 4H), 7.26—7.24(m, 1H), 7.16—7.14(m, 1H), 3.87(s, 3H), 3.43(s, 3H)	159.3, 158.2, 151.0, 150.4, 146.71, 138.3, 136.0, 129.8, 127.9, 127.4, 126.5, 126.2, 125.9, 118.3, 105.7, 29.2, 27.5
3x	7.73—7.72(m, 1H), 7.56—7.54(m, 1H), 7.48—7.46(m, 3H), 7.35—7.33(m, 3H), 7.16—7.14(m, 1H), 3.83(s, 3H), 3.37(s, 3H)	159.3, 154.1, 153.3, 150.8, 150.5, 142.3, 138.4, 129.5, 127.5, 127.2, 126.8, 126.7, 126.4, 115.7, 105.1, 29.1, 27.4
5a	8.60(d, J=4.9 Hz, 1H), 7.46—7.44(m, 3H), 7.30—7.26(m, 2H), 7.01(d, J=4.9 Hz, 1H), 3.78(s, 3H), 3.37(s, 3H)	159.5, 153.5, 151.0, 150.3, 138.1, 127.2, 126.8, 121.0, 107.1, 29.2, 27.5
5b	7.44—7.42(m, 3H), 7.29—7.26(m, 2H), 6.87(s, 1H), 3.77(s, 3H), 3.36(s, 3H), 2.61(s, 3H)	161.6, 159.6, 153.4, 150.5, 138.4, 127.0, 126.7, 120.7, 104.5, 29.0, 27.3, 23.9
5c	7.25—7.23(m, 4H), 6.85(s, 1H), 3.76(s, 3H), 3.36(s, 3H), 2.60(s, 3H), 2.41(s, 3H)	161.5, 159.7, 153.6, 150.6, 150.6, 136.9, 135.4, 127.5, 126.7, 120.8, 104.6, 29.0, 27.4, 23.9, 20.3
5d	13.23(s, 1H), 7.52(s, 1H), 7.39—7.37(m, 1H), 7.04—7.02(m, 1H), 6.98—6.94(m, 1H), 3.74(s, 3H), 3.47(s, 3H), 2.91(s, 3H)	160.1, 159.1, 158.5, 153.7, 145.0, 149.3, 132.3, 126.3, 118.5, 117.7, 116.7, 116.2, 106.2, 29.4, 27.5, 22.1

Compd.	Product	Yield^b(%)	Time/min	Compd.	Product	Yield^b(%)	Time/min
3a		88	10	3h		78	13
3b		85	11	3i		82	15
3c		83	11	3j		81	15
3d		85	12	3k		80	13
3e		79	10	3l		88	10
3f		78	11	3m		85	10
3g		81	14	3n		85	11
Compd.	Product	Yield^b(%)	Time/min	Compd.	Product	Yield^b(%)	Time/min
3o		84	12	3t		78	15
3p		81	13	3u		84	13
3q		82	12	3v		80	13
3r		79	12	3w		81	11
3s		77	11	3x		83	10

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