POTKIN et al.
134
(E)-2-Ethoxy-4-(2-hydroxyphenyliminomethyl)-
(E)-5-(Biphenyl-4-yliminomethyl)-2-methoxy-
phenyl 5-(4-methylphenyl)isoxazole-3-carboxylate
(XXXIV). Yield 72%, mp 182–183°C. IR spectrum, ν,
cm–1: 1772 (C=O, ester); 1627 (CH=N); 1612, 1595,
1575, 1504, 1483, 1454, 1432 (C=C, C=N); 1271,
phenyl 5-phenylisoxazole-3-carboxylate (XXXI).
Yield 74%, mp 139–140°C. IR spectrum, ν, cm–1: 1761
(C=O, ester); 1626 (CH=N); 1604, 1590, 1509, 1456,
1446, 1431, 1384 (C=C, C=N); 1281, 1214, 1183,
1
1
1139, 1118 (C–O). H NMR spectrum, δ, ppm: 1.39 t
1201, 1137, 1107 (C–O). H NMR spectrum, δ, ppm:
(3H, Me), 4.19 q (2H, CH2O), 6.90–7.87 m (13H,
2.41 s (3H, Me), 3.90 s (3H, MeO), 7.08 (1H, 4-H),
7.10–7.87 m (16H, Harom), 8.44 s (1H, CH=N).
13C NMR spectrum, δC, ppm: 21.55 (CH3), 56.16
(OCH3), 99.77 (C4), 112.27 (CHarom), 115.36 (CHarom),
121.37 (2C, CHarom), 125.93 (2C, CHarom), 127.17
(CHarom), 127.85 (2C, CHarom), 128.64 (2C, CHarom),
128.97 (CHarom), 129.87 (2C, CHarom); 123.84, 129.75,
138.81, 139.43, 140.62, 141.39, 150.98, 153.61,
156.05, 157.82 (Carom, C3, C5); 158.22 (CH=N), 172.33
(C=O). Found, %: C 76.57; H 5.10; N 5.28. M 474.
C31H24N2O4. Calculated, %: C 76.21; H 4.95; N 5.73.
M 488.53.
H
arom, 4-H), 8.65 s (1H, CH=N), 11.98 br.s (1H, OH).
13C NMR spectrum, δC, ppm: 14.63 (CH3), 64.80
(OCH2), 100.30 (C4), 112.01 (CHarom), 115.14 (CHarom),
116.08 (CHarom), 120.23 (CHarom), 122.79 (CHarom),
122.96 (CHarom), 126.02 (2C, CHarom), 129.12 (CHarom),
129.23 (2C, CHarom), 131.00 (CHarom); 126.53, 135.32,
135.45, 142.18, 150.88, 152.23, 156.09, 157.56 (Carom
,
C3, C5); 156.38 (CH=N), 172.18 (C=O). Found, %:
C 70.41; H 5.01; N 6.22. M 417. C25H20N2O5. Calcu-
lated, %: C 70.08; H 4.71; N 6.54. M 428.44.
(E)-4-(Biphenyl-4-yliminomethyl)-2-methoxy-
phenyl 5-(4-methylphenyl)isoxazole-3-carboxylate
(XXXII). Yield 73%, mp 158–159°C. IR spectrum, ν,
cm–1: 1748 (C=O, ester); 1627 (CH=N); 1596, 1507,
1483, 1447, 1417 (C=C, C=N); 1277, 1227, 1197,
(E)-5-(4-Bromophenyliminomethyl)-2-methoxy-
phenyl 5-(4-methylphenyl)isoxazole-3-carboxylate
(XXXV). Yield 76%, mp 137–138°C. IR spectrum, ν,
cm–1: 1770 (C=O, ester); 1636 (CH=N); 1609, 1572,
1507, 1482, 1453, 1428 (C=C, C=N); 1278, 1223,
1
1151, 1119, 1034 (C–O). H NMR spectrum, δ, ppm:
2.41 s (3H, Me), 3.93 s (3H, MeO), 7.01 (1H, 4-H),
7.30–7.75 m (16H, Harom), 8.48 s (1H, CH=N).
13C NMR spectrum, δC, ppm: 21.53 (CH3), 56.14
(OCH3), 99.79 (C4), 110.81 (CHarom), 121.40 (2C,
CHarom), 122.85 (CHarom), 123.09 (CHarom), 125.93 (2C,
CHarom), 126.92 (2C, CHarom), 127.25 (CHarom), 127.88
(2C, CHarom), 128.81 (2C, CHarom), 129.87 (2C,
CHarom); 123.85, 135.83, 139.10, 140.55, 141.40,
141.69, 150.84, 151.55, 156.06, 157.66 (Carom, C3, C5);
158.95 (CH=N), 172.35 (C=O). Found, %: C 76.52;
H 5.17; N 5.51. M 469. C31H24N2O4. Calculated, %:
C 76.21; H 4.95; N 5.73. M 488.53.
1
1200, 1138, 1107 (C–O). H NMR spectrum, δ, ppm:
2.42 s (3H, Me), 3.90 s (3H, MeO), 7.00–7.84 m (12H,
H
arom, 4-H), 8.34 s (1H, CH=N). 13C NMR spectrum,
δC, ppm: 21.54 (CH3), 56.14 (OCH3), 99.78 (C4),
110.81 (CHarom), 122.60 (2C, CHarom), 122.91 (CHarom),
123.18 (CHarom), 125.93 (2C, CHarom), 129.88 (2C,
CHarom), 132.24 (2C, CHarom); 119.52, 123.83, 135.51,
141.43, 141.87, 150.69, 151.57, 156.02, 157.62 (Carom
,
C3, C5); 159.54 (CH=N), 172.38 (C=O). Found, %:
C 61.45; H 4.08; Br 15.93; N 5.56. M 484.
C25H19BrN2O4. Calculated, %: C 61.11; H 3.90;
Br 16.26; N 5.70. M 491.33.
(E)-4-(4-Bromophenyliminomethyl)-2-methoxy-
phenyl 5-(4-methylphenyl)isoxazole-3-carboxylate
(XXXIII). Yield 76%, mp 167–168°C. IR spectrum, ν,
cm–1: 1746 (C=O, ester); 1623 (CH=N); 1597, 1507,
1476, 1465, 1448, 1416, 1377 (C=C, C=N); 1277,
1228, 1196, 1151, 1126, 1116, 1102, 1033, 991 (C–O).
1H NMR spectrum, δ, ppm: 2.42 s (3H, Me), 3.92 s
(3H, MeO), 7.01–7.73 m (12H, Harom, 4-H), 8.39 s
(1H, CH=N). 13C NMR spectrum, δC, ppm: 21.56
(CH3), 56.17 (OCH3), 99.75 (C4), 112.28 (CHarom),
122.53 (CHarom), 122.59 (2C, CHarom), 125.92 (2C,
CHarom), 129.11 (CHarom), 129.88 (2C, CHarom), 132.17
(2C, CHarom); 119.19, 123.81, 129.42, 139.43, 141.42,
150.82, 153.78, 156.00, 157.80 (Carom, C3, C5); 158.77
(CH=N), 172.36 (C=O). Found, %: C 61.37; H 3.82;
Br 15.90; N 5.44. M 480. C25H19BrN2O4. Calculated,
%: C 61.11; H 3.90; Br 16.26; N 5.70. M 491.33.
(E)-2-(Biphenyl-4-yliminomethyl)-6-methoxy-
phenyl 5-(4-methylphenyl)isoxazole-3-carboxylate
(XXXVI). Yield 77%, mp 178–179°C. IR spectrum, ν,
cm–1: 1780 (C=O, ester); 1620 (CH=N); 1610, 1599,
1578, 1520, 1481, 1450, 1437 (C=C, C=N); 1284,
1
1218, 1202, 1166, 1130, 1114, 1072 (C–O). H NMR
spectrum, δ, ppm: 2.41 s (3H, Me), 3.87 s (3H, MeO),
7.03 (1H, 4-H), 7.13–7.80 m (16H, Harom), 8.69 s (1H,
CH=N). 13C NMR spectrum, δC, ppm: 21.54 (CH3),
56.24 (OCH3), 99.88 (C4), 114.84 (CHarom), 120.04
(CHarom), 121.42 (2C, CHarom), 125.93 (2C, CHarom),
126.91 (2C, CHarom), 127.21 (CHarom), 127.24 (CHarom),
127.82 (2C, CHarom), 128.75 (2C, CHarom), 129.87 (2C,
CHarom); 123.82, 129.40, 139.25, 139.46, 140.52,
141.40, 150.92, 151.35, 155.92, 157.77 (Carom, C3, C5);
154.43 (CH=N), 172.38 (C=O). Found, %: C 76.54;
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 48 No. 1 2012