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H, 4.71; N, 6.54; O, 18.67. Found: C, 70.01; H, 4.72; N, 6.50; O,
18.60.
64.87; H, 4.14; N, 6.05; O, 17.28; Cl, 7.66. Found: C, 64.85; H,
4.15; N, 6.01; O, 17.22; Cl, 7.60.
4.1.3.24. Trans-4-[(3H,3aH,6aH)-3-phenyl-4,6-dioxo-2p-tolydi-
hydro-2H-pyrrolo[3,4-d]isoxazol-5(3H,6H,6aH)-yl]benzoic acid
4.1.3.30. Trans-4-[(3H,3aH,6aH)-3-(2-chlorophenyl)-4,6-dioxo-
2p-tolydihydro-2H-pyrrolo[3,4-d]isoxazol-5(3H,6H,6aH)-
(8aa0).
White solid, yield 30%, mp 161–162 °C; IR (Nujol)
t
yl]benzoic acid (8da0).
183 °C; IR (Nujol)
1H NMR (DMSO, 400 MHz) d 5.82 (1H, s, H3,), 5.14–5.16 (1H, d,
3a, J = 7.22 Hz), 5.02–5.04 (1H, d, H6a, J = 7.88 Hz), 6.51–7.89
White solid, yield 30%, mp 182–
1716, 1684, 1595, 1370, 1284, 1212 cmꢁ1; 1H NMR (DMSO,
400 MHz) d 5.65 (1H, s, H3,), 5.12–5.14 (1H, d, H3a, J = 7.57 Hz),
4.15–4.17 (1H, d, H6a, J = 7.52 Hz), 6.29–7.96 (13H, m, aromatic
H), 10.01 (1H, s, COOH), 2.25 (3H, s, CH3); MS: m/z 430 (M+H)+;
Anal. Calcd for C25H20N2O5: C, 70.08; H, 4.71; N, 6.54; O, 18.67.
Found: C, 69.95; H, 4.35; N, 6.43; O, 18.42.
t
1717, 1685, 1601, 1389, 1272, 1205 cmꢁ1
;
H
(12H, m, aromatic H), 10.01 (1H, s, COOH), 2.24 (3H, s, CH3); MS:
m/z 464.5 (M+H)+; Anal. Calcd for C25H19ClN2O5: C, 64.87; H,
4.14; N, 6.05; O, 17.28; Cl, 7.66. Found: C, 64.75; H, 4.12; N, 5.85;
O, 17.15; Cl, 7.52.
4.1.3.25. Cis-4-[(3H,3aH,6aH)-3-(2-hydroxyphenyl)-4,6-dioxo-
2p-tolydihydro-2H-pyrrolo[3,4-d]isoxazol-5(3H,6H,6aH)-
4.1.3.31. Cis-4-[(3H,3aH,6aH)-3-(3-chlorophenyl)-4,6-dioxo-2p-
tolydihydro-2H-pyrrolo[3,4-d]isoxazol-5(3H,6H,6aH)-yl]benzoic
yl]benzoic acid (8ba).
(Nujol)
3310, 1715, 1693, 1600, 1383, 1286, 1206 cmꢁ1; 1H
NMR (DMSO, 400 MHz) d 5.23–5.25 (1H, d, H3, J = 7.90 Hz), 5.02–
5.05 (1H, q, H3a, J = 7.39 and 7.89 Hz), 4.17–4.19 (1H, d, H6a
White solid, yield 48%, mp 204 °C; IR
t
acid (8ea).
1715, 1689, 1609, 1392, 1276, 1206 cmꢁ1; 1H NMR (DMSO,
400 MHz) d 5.21–5.23 (1H, d, H3, J = 7.24 Hz), 4.46–4.49 (1H, q,
3a, J = 7.32 and 7.88 Hz), 4.29–4.31 (1H, d, H6a, J = 8.33 Hz),
White solid, yield 53%, mp 202–203 °C; IR (Nujol)
t
,
J = 7.80 Hz), 6.45–8.01 (12H, m, aromatic H), 11.8 (1H, s, COOH),
8.35 (1H, s OH), 2.19 (3H, s, CH3); 8MS: m/z 446 (M+H)+; Anal.
Calcd for C25H20N2O6: C, 67.56; H, 4.54; N, 6.30; O, 21.60. Found:
C, 67.52; H, 4.49; N, 6.32; O, 21.47.
H
6.72–7.84 (12H, m, aromatic H), 9.7 (1H, s, COOH), 2.22 (3H, s,
CH3); MS: m/z 464.5 (M+H)+; Anal. Calcd for C25H19ClN2O5: C,
64.87; H, 4.14; N, 6.05; O, 17.28; Cl, 7.66. Found: C, 63.84; H,
4.02; N, 5.97; O, 17.25; Cl, 7.57.
4.1.3.26.
dioxo-2p-tolydihydro-2H-pyrrolo[3,4-d]isoxazol-5(3H,6H,6aH)-
yl]benzoic acid (8ba0).
White solid, yield 26%, mp 185–
186 °C; IR (Nujol) 3300, 1714, 1693, 1602, 1382, 1287, 1204 cm
Trans-4-[(3H,3aH,6aH)-3-(2-hydroxyphenyl)-4,6-
4.1.3.32. Trans-4-[(3H,3aH,6aH)-3-(3-chlorophenyl)-4,6-dioxo-
2p-tolydihydro-2H-pyrrolo[3,4-d]isoxazol-5(3H,6H,6aH)-
t
yl]benzoic acid (8ea0).
148 °C; IR (Nujol)
1H NMR (DMSO, 400 MHz) d 5.73 (1H, s, H3,), 5.40–5.42 (1H, d,
3a, J = 7.52 Hz), 5.22–5.24 (1H, d, H6a, J = 7.16 Hz), 6.88–8.02
White solid, yield 26%, mp 146–
ꢁ1; 1H NMR (DMSO, 400 MHz) d 5.92 (1H, s, H3,), 5.05–5.07 (1H,
d, H3a, J = 7.47 Hz), 4.07–4.09 (1H, d, H6a, J = 7.42 Hz), 6.45–7.98
(12H, m, aromatic H), 9.2 (1H, s, COOH), 8.34 (1H, s, OH), 2.21
(3H, s, CH3); MS: m/z 446 (M+H)+; Anal. Calcd for C25H20N2O6: C,
67.56; H, 4.54; N, 6.30; O, 21.60. Found: C, 66.99; H, 4.36; N,
6.27; O, 21.51.
t
1717, 1682, 1602, 1381, 1271, 1200 cmꢁ1
;
H
(12H, m, aromatic H), 10.01 (1H, s, COOH), 2.19 (3H, s, CH3); MS:
m/z 464.5 (M+H)+; Anal. Calcd for C25H19ClN2O5: C, 64.87; H,
4.14; N, 6.05; O, 17.28; Cl, 7.66. Found: C, 64.85; H, 4.10; N, 5.90;
O, 17.20; Cl, 7.46.
4.1.3.27. Cis-4-[(3H,3aH,6aH)-3-(4-hydroxyphenyl)-4,6-dioxo-
2p-tolydihydro-2H-pyrrolo[3,4-d]isoxazol-5(3H,6H,6aH)-
4.1.3.33. Cis-4-[(3H,3aH,6aH)-3-(4-chlorophenyl)-4,6-dioxo-2p-
tolydihydro-2H-pyrrolo[3,4-d]isoxazol-5(3H,6H,6aH)-yl]benzoic
yl]benzoic acid (8ca).
White solid, yield 59%, mp 227–
3310, 1713, 1688, 1607, 1380, 1287, 1160 cm
1H NMR (DMSO, 400 MHz) d 5.23–5.25 (1H, d, H3,
acid (8fa).
White solid, yield 50%, mp 220 °C; IR (Nujol) t
228 °C; IR (Nujol)
;
t
1711, 1691, 1605, 1390, 1285, 1145 cmꢁ1; 1H NMR (DMSO,
ꢁ1
400 MHz) d 4.95–4.97 (1H, d, H3, J = 8.20 Hz), 4.18–4.23 (1H, q,
J = 7.82 Hz), 5.35–5.38 (1H, q, H3a, J = 7.02 and 7.51 Hz), 4.25–
4.27 (1H, d, H6a, J = 7.72 Hz), 6.50–8.24 (12H, m, aromatic H),
12.1 (1H, s, COOH), 8.50 (1H, s, OH), 2.25 (3H, s, CH3); MS: m/z
446 (M+H)+; Anal. Calcd for C25H20N2O6: C, 67.56; H, 4.54; N,
6.30; O, 21.60. Found: C, 67.02; H, 4.39; N, 6.09; O, 20.85.
H3a, J = 7.12 and 8.58 Hz), 4.09–4.11 (1H, d, H6a, J = 7.31 Hz),
6.70–8.02 (12H, m, aromatic H), 10.4 (1H, s, COOH), 2.25 (3H, s,
CH3); MS: m/z 464.5 (M+H)+; Anal. Calcd for C25H19ClN2O5: C,
64.87; H, 4.14; N, 6.05; O, 17.28; Cl, 7.66. Found: C, 64.25; H,
4.03; N, 6.01; O, 17.16; Cl, 7.33.
4.1.3.28.
dioxo-2p-tolydihydro-2H-pyrrolo[3,4-d]isoxazol-5(3H,6H,6aH)-
yl]benzoic acid (8ca0).
White solid, yield 24%, mp 210–
212 °C; IR (Nujol) 3312, 1711, 1679, 1606, 1380, 1285, 1164 cm
Trans-4-[(3H,3aH,6aH)-3-(4-hydroxyphenyl)-4,6-
4.1.3.34. Trans-4-[(3H,3aH,6aH)-3-(4-chlorophenyl)-4,6-dioxo-
2p-tolydihydro-2H-pyrrolo[3,4-d]isoxazol-5(3H,6H,6aH)-
yl]benzoic acid (8fa0).
167 °C; IR (Nujol)
1H NMR (DMSO, 400 MHz) d 5.65 (1H, s, H3,), 5.25–5.27 (1H, d,
3a, J = 7.66 Hz), 5.16–5.18 (1H, d, H6a, J = 7.16 Hz), 6.67–7.98
White solid, yield 31%, mp 165–
t
t
1712, 1687, 1607, 1378, 1283, 1158 cmꢁ1
;
ꢁ1; 1H NMR (DMSO, 400 MHz) d 6.04 (1H, s, H3,), 5.37–5.39 (1H,
d, H3a, J = 7.23 Hz), 4.28–4.30 (1H, d, H6a, J = 7.23 Hz), 6.71–8.20
(12H, m, aromatic H), 11.95 (1H, s, COOH), 8.74 (1H, s, OH),(2.27
(3H, s, CH3); MS: m/z 446 (M+H)+; Anal. Calcd for C25H20N2O6: C,
67.56; H, 4.54; N, 6.30; O, 21.60. Found: C, 67.50; H, 4.53; N,
6.28; O, 21.55.
H
(12H, m, aromatic H), 9.99 (1H, s, COOH), 2.15 (3H, s, CH3); MS:
m/z 464.5 (M+H)+; Anal. Calcd for C25H19ClN2O5: C, 64.87; H,
4.14; N, 6.05; O, 17.28; Cl, 7.66. Found: C, 64.23; H, 4.07; N, 6.02;
O, 17.23; Cl, 7.42.
4.1.3.29. Cis-4-[(3H,3aH,6aH)-3-(2-chlorophenyl)-4,6-dioxo-2p-
tolydihydro-2H-pyrrolo[3,4-d]isoxazol-5(3H,6H,6aH)-yl]benzoic
4.1.3.35. Cis-4-[(3H,3aH,6aH)-3-(2-methoxyphenyl)-4,6-dioxo-
2p-tolydihydro-2H-pyrrolo[3,4-d]isoxazol-5(3H,6H,6aH)-
acid (8da).
White solid, yield 43%, mp 200 °C; IR (Nujol) t
yl]benzoic acid (8ga).
202 °C; IR (Nujol)
1713, 1693, 1600, 1390, 1282, 1189 cmꢁ1
NMR1H NMR (DMSO, 400 MHz) 5.02–5.04 (1H, d, H3,
White solid, yield 35%, mp 200–
1715, 1686, 1601, 1386, 1272, 1201 cmꢁ1; 1H NMR (DMSO,
t
;
1H
400 MHz) d 5.25–5.27 (1H, d, H3, J = 7.40 Hz), 4.21–4.25 (1H, q,
d
H3a, J = 7.46 and 8.11 Hz), 4.12–4.14 (1H, d, H6a, J = 7.25 Hz),
J = 7.884 Hz), 4.78–4.83 (1H, q, H3a, J = 7.75 and 8.11 Hz), 424–
4.26 (1H, d, H6a, J = 7.87 Hz), 6.46–7.97 (12H, m, aromatic H),
10.2 (1H, s, COOH), 3.70 (1H, s, OCH3), 2.27 (3H, s, CH3); MS: m/z
6.83–8.01 (12H, m, aromatic H), 9.92 (1H, s, COOH), 2.22 (3H, s,
CH3); MS: m/z 464.5 (M+H)+; Anal. Calcd for C25H19ClN2O5: C,