Page 9 of 15
The Journal of Organic Chemistry
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(
E)-1-(2-hydroxyphenyl)-3-(naphthalen-1-yl)prop-2-en-1-one (1c) Prepared via General Procedure A, 94%, H NMR
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300 MHz, CDCl ) δ 12.89 (s, 1H), 8.77 (d, J = 9.8 Hz, 1H), 8.25 (d, J = 8.3 Hz, 1H), 7.95-7.87 (m, 4H), 7.72 (d, J = 15.2 Hz, 1H),
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.61-7.47 (m, 4H), 7.05 (dd, J = 8.4, 1.1 Hz, 1H), 6.94 (ddd, J = 8.2, 7.2, 1.1 Hz, 1H); C NMR (126 MHz, CDCl ) δ 193.8, 163.9,
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42.6, 136.7, 134.0, 132.2, 132.0, 131.4, 130.0, 129.0, 127.3, 126.6, 125.6, 125.5, 123.6, 123.0, 120.2, 119.1, 118.9; IR (Neat) 3056, 2366,
637, 1606, 1567, 1488, 1437, 1393, 1355, 1335, 1304, 1276, 1200, 1174, 1155, 1127, 1027, 992, 951, 909, 857, 847, 818, 757, 728, 690,
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60, 626 cm .
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(E)-3-([1,1'-biphenyl]-4-yl)-1-(2-hydroxyphenyl)prop-2-en-1-one (1d) Prepared via General Procedure A, 66%, H
NMR (300 MHz, CDCl ) δ 12.85 (s, 1H), 7.98-7.92 (m, 2H), 7.75-7.71 (m, 3H), 7.67-7.60 (m, 5H), 7.53-7.35 (m, 4H), 7.03 (dd,
J = 8.4, 1.1 Hz, 1H), 6.95 (ddd, J = 8.2, 7.2, 1.2 Hz, 1H); C NMR (126 MHz, CDCl ) δ 193.9, 163.8, 145.2, 143.9, 140.2, 136.6,
133.8, 129.9, 128.2, 120.3, 120.1, 119.0, 118.9; IR (Neat) 3057, 3033, 2360, 2342, 1637, 1583, 1557, 1520, 1487, 1450, 14340, 1409,
1362, 1345, 1324, 1309, 1284, 1273, 1237, 1203, 1157, 1129, 1078, 1025, 1006, 990, 947, 911, 869, 833, 792, 752, 717, 690, 660, 615,
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590, 565, 530 cm .
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(
E)-3-(furan-2-yl)-1-(2-hydroxyphenyl)prop-2-en-1-one (1e) Prepared via General Procedure A, 85%, H NMR (500
MHz, CDCl ) δ 12.87 (s, 1H), 7.90 (d, J = 8.0, 1H), 7.65 (d, J = 15.2 Hz, 1H), 7.54 (t, J = 6.3, 2H), 7.47 (t, J = 8.3 Hz, 1H), 7.00
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d, J = 8.4 Hz, 1H), 6.92 (t, J = 7.5 Hz, 1H), 6.75 (d, J = 3.4 Hz, 1H), 6.52 (d, J = 0.9 Hz, 1H); C NMR (126 MHz, CDCl ) δ
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93.5, 163.8, 151.7, 145.6, 136.5, 131.3, 128.8, 120.3 ,119.0, 18.7, 117.8, 117.3, 113.1; IR (Neat) 3149, 3127, 3095, 1636, 1574, 1552, 1509,
487, 1473, 1440, 1390, 1361, 1336, 1306, 1270, 1258, 1212, 1189, 1158, 1079, 1014, 968, 929, 910, 857, 831, 829, 793, 743, 720, 695,
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51, 592, 564 cm .
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(
E)-1-(2-hydroxyphenyl)-3-(thiophen-2-yl)prop-2-en-1-one (1f) Prepared via General Procedure A, 56%, H NMR (500
MHz, CDCl ) δ 12.83 (s, 1H), 8.04 (d, J = 15.1 Hz, 1H), 7.87 (dd, J = 8.1, 1.6 Hz, 1H), 7.48 (ddd, J = 8.6, 7.3, 1.6 Hz, 1H), 7.45 (d,
J = 5.0 Hz, 1H), 7.42 (d, J = 15.2Hz, 1H), 7.39 (d, J = 3.6 Hz, 1H), 7.11-7.09 (m, 1H) , 7.00 (dd, J = 8.4, 1.1 Hz, 1H), 6.93 (ddd, J =
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.2, 1.2 Hz, 1H); C NMR (126 MHz, CDCl ) δ 196.4, 163.8, 140.4, 138.1, 136.6, 133.0, 127.7, 128.7, 120.2, 119.1, 119.0, 118.8; IR
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Neat) 3101, 3086, 3071, 3024, 1690, 1632, 1605, 1573, 1557, 1507, 1482, 1436, 1419, 1378, 1343, 1328, 1298, 1265, 1237, 1221, 1206,
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177, 1148, 1124, 1077, 1047, 1020, 974, 878, 848, 836, 814, 762, 722, 707, 685, 660, 597 cm .
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E)-1-(2-hydroxyphenyl)-3-(thiophen-3-yl)prop-2-en-1-one (1g) Prepared via General Procedure A, 48%, H NMR
500 MHz, CDCl ) δ 12.83 (s, 1H), 7.92-7.87 (m, 2H), 7.64 (dd, J = 2.7, 0.9 Hz, 1H), 7.49-7.4394 (m, 2H), 7.43 (dd, J = 5.1, 1.2
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Hz, 1H), 7.38 (dd, J = 4.9, 2.8 Hz, 1H), 7.01(dd, J = 8.4, 1.1 Hz, 1H), 6.92 (ddd, J = 8.2, 7.4, 1.2 Hz, 1H); C NMR (126 MHz,
CDCl ) δ 194.1, 163.8, 139.0, 138.2, 136.5, 130.2, 129.8, 127.5, 125.4, 120.2, 120.0; IR (Neat) 3097.8, 2360, 2341, 1688, 1634, 1566,
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515, 1486, 1463, 1442, 1421, 1393, 1355, 1336, 1302, 1258, 1235, 1199, 1153, 1127, 1085, 1021, 973, 864, 829, 809, 793, 752, 696, 651,
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05, 594 cm .
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E)-1-(2-hydroxynaphthalen-1-yl)-3-phenylprop-2-en-1-one (1h) Prepared via General Procedure D, 67%, H NMR
500 MHz, CDCl ) δ 12.59 (s, 1H), 8.08 (d, J = 8.5 Hz, 1H), 7.95 (d, 4.5 Hz, 1H), 7.93 (d, J = 2.1 Hz, 1H), 7.84-7.82 (m, 1H),
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.65-7.64 (m, 2H), 7.55 (ddd, 8.5, 6.8, 1.3 Hz, 1H), 7.53 (d, J = 15.6 Hz, 1H), 7.44-7.45 (m, 3H), 7.41-7.42 (m, 1H), 7.20 (d, J =
.0 Hz, 1H) (76 MHz, CDCl ) δ 194.8, 163.0, 143.3, 137.1, 135.0, 131.8, 130.9, 128.5, 129.3, 128.9, 128.1, 127.3, 125.4, 124.2, 119.7,
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16.1; IR (Neat) 2360, 2341, 1634, 1621, 1597, 1571, 1513, 1496, 1463, 1407, 1370, 1340, 1299, 1276, 1243, 1183, 1157, 1107, 994, 973,
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26, 758, 717, 684, 658, 644, 605, 581, 562, 547 cm .
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E)-1-(1-hydroxynaphthalen-2-yl)-3-phenylprop-2-en-1-one (1i) Prepared via General Procedure A, 57%, H NMR
500 MHz, CDCl ) δ 14.82 (s, 1H), 8.49 (d, J = 8.5 Hz, 1H), 7.97 (d, J = 15.5 Hz, 1H), 7.84 (d, J = 8.5 Hz, 1H), 7.76 (dd, J = 8.5,
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6.5 Hz, 2H), 7.69 (dd, J = 7.0, 4.0 Hz, 2H), 7.63 (ddd, J = 8.0, 7.0, 1.5 Hz, 1H), 7.53 (ddd, J = 8.5, 7.5, 1.0 Hz, 1h) 7.44 (dd, J =
5.0, 1.5 Hz, 3H), 7.30 (d, J = 8.5 Hz, 1H); C NMR (126 MHz, CDCl ) δ 193.5, 164.7, 145.3, 137.6, 135.0, 130.5, 129.3, 128.9, 127.6,
126.2, 125.7, 124.8, 124.2, 120.7, 118.5, 113.7; IR (Neat) 2360, 2342, 1626, 1597, 1573, 1495, 1467, 1448, 1418, 1339, 1352, 1323, 1301,
1282, 1223, 1207, 1150, 1119, 1062, 1023, 1000, 971, 902, 854, 804, 790, 765, 742, 709, 683, 669, 651, 570 cm .
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(E)-1-(4-fluoro-2-hydroxyphenyl)-3-(furan-2-yl)prop-2-en-1-one (1j) Prepared via General Procedure B, 63% fla-
vanone, 8% chalcone, H NMR (300 MHz, CDCl ) δ 13.26 (s, 1H), 7.91 (dd, J = 8.9, 6.5 Hz, 1H), 7.66 (d, J = 15.1 Hz, 1H), 7.54
(d, J = 1.53 Hz, 1H), 7.45 (d, J = 15.1 Hz, 1H), 6.76 (d, J = 16.9 Hz, 1H), 6.70-6.60 (m, 2H), 6.53 (dd, J = 3.4, 1.8 Hz, 1H); C
NMR (75 MHz, CDCl ) δ 192.4, 169.3, 166.4, 166.2, 165.9, 151.6, 145.7, 132.2, 132.1, 131.5, 117.6, 117.6, 117.3,117.3, 113.2, 107.5, 107.2,
105.4, 105.1; IR (Neat) 1610, 1595, 1571, 1549, 1511, 1477, 1416, 1370, 1345, 1298, 1278, 1264, 1234, 1212, 1191, 1164, 1078, 1015, 974,
959, 929, 883, 853, 828, 805, 745, 716, 689, 641, 605, 590, 578 cm .
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(
E)-1-(2-hydroxy-4-methoxyphenyl)-3-(thiophen-2-yl)prop-2-en-1-one (1k) Prepared via General Procedure A, 86%,
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H NMR (300 MHz, CDCl ) δ 13.44 (s, 1H), 7.99 (d, J = 15.2 Hz, 1H), 7.77 (d, J = 8.6 Hz, 1H), 7.42 (d, J = 5.1 Hz, 1H) 7.36 (s,
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H), 7.33 (d, J = 12.2 Hz, 1H), 7.08 (dd, J = 5.1, 3.7 Hz, 1H), 6.49-6.45 (m, 2H), 3.84 (s, 3H); C NMR (126 MHz, CDCl ) δ
91.5, 166.9, 166.4, 140.5, 137.1, 132.5, 131.3, 129.3, 128.6, 119.3, 114.2, 108.0, 101.3, 55.8; IR (Neat) 3104, 3082, 3006, 2968, 2936,
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