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HETEROCYCLES, Vol. 81, No. 3, 2010
(3de): Yield (65%); orange solid; Mp 212 °C; 1H NMR (300 MHz, CDCl3) δ 5.25 (s, 4-H), 7.05-8.26 (m,
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aromatic H) ppm; C NMR (75.5 MHz, CDCl3) δ 67.20 (C-4), 90.90 (C-5,4’), 125.50-159.93 (C-3 and
aromatic C), 168.46 (C=O), 172.20 (C=O) ppm.
(5R*,4:4’R*)-Spiro[5-(p-nitrophenyl)-3-phenylisoxazoline-4,4’-(2’-phenyl)isoquinoline-1’,3’-dione]
(4de): Yield (20%); yellow solid; Mp 165 °C; 1H NMR (300 MHz, CDCl3) δ 6.28 (s, 5-H), 7.10-8.20 (m,
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aromatic H) ppm; C NMR: (75.5 MHz, CDCl3) δ 97.60 (C-5), 70.87 (C-4,4’), 124.64-160.34 (C-3 and
aromatic C), 168.43 (C=O), 171.40 (C=O) ppm; Anal. Calcd for C29H19N3O5: C, 71.16; H, 3.91; N, 8.58.
Found: C, 71.09; H, 3.80; N, 8.65.
(4S*,5:4’R*)-Spiro[4-phenyl-3-(p-tolyl)isoxazoline-5,4’-(2’–phenyl)isoquinoline-1’,3’-dione] (3af):
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Yield (61%); white solid; Mp 190 °C; H NMR (300 MHz, CDCl3) δ 2.21 (s, CH3), 5.22 (s, 4-H),
6.75-8.00 (m, aromatic H) ppm; 13C NMR (75.5 MHz, CDCl3) δ 21.88 (CH3), 67.11 (C-4), 90.61 (C-5,4’),
125.19-159.25 (C-3 and aromatic C), 164.28 (C=O), 172.03 (C=O) ppm.
(5R*,4:4’R*)-Spiro[5-phenyl-3-(p-tolyl)isoxazoline-4,4’-(2’-phenyl)isoquinoline-1’,3’-dione] (4af):
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Yield (23%); yellow solid; Mp 210 °C; H NMR (300 MHz, CDCl3) δ 2.22 (s, CH3), 6.19 (s, 5-H),
6.56-7.96 (m, aromatic H) ppm; 13C NMR (75.5 MHz, CDCl3) δ 21.90 (CH3), 96.75 (C-5), 70.90 (C-4,4’),
124.43-159.41 (C-3 and aromatic C), 163.63 (C=O), 171.52 (C=O) ppm.
(4S*,5:4’R*)-Spiro[3-(p-tolyl)-4-(p-tolyl)isoxazoline-5,4’-(2’-phenyl)isoquinoline-1’,3’-dione] (3bf):
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Yield (60%); colourless solid; Mp 240 °C; H NMR (300 MHz, CDCl3) δ 2.21 (s, CH3), 2.32 (s, CH3),
5.21(s, 4-H), 6.75-8.01 (m, aromatic H) ppm; 13C NMR (75.5 MHz, CDCl3) δ 21.43 (CH3), 21.65 (CH3),
67.00 (C-4), 90.67 (C-5,4’), 124.92-160.30 (C-3 and aromatic C), 164.26 (C=O), 172.09 (C=O) ppm.
Anal. Calcd for C31H24N2O3: C, 78.80; H, 5.12; N, 5.93. Found: C, 78.71; H, 5.23; N, 5.99.
(5R*,4:4’R*)-Spiro[3-(p-tolyl)-5-(p-tolyl)isoxazoline-4,4’-(2’-phenyl)isoquinoline-1’,3’-dione] (4bf):
Yield (25%); yellow solid; Mp 215 °C; 1H NMR (300 MHz, CDCl3) δ 2.23 (s, CH3), 2.34 (s, CH3), 6.16
(s, 5-H), 6.85-8.09 (m, aromatic H) ppm; 13C NMR (75.5 MHz, CDCl3) δ 21.51 (CH3), 21.77 (CH3),
96.94 (C-5), 70.86 (C-4,4’), 124.13-160.09 (C-3 and aromatic C), 163.68 (C=O), 171.54 (C=O) ppm.
(4S*,5:4’R*)-Spiro[4-(p-anisyl)-3-(p-tolyl)isoxazoline-5,4’-(2’-phenyl)isoquinoline-1’,3’-dione] (3cf):
Yield (62%); colourless solid; Mp 230 °C; 1H NMR (300 MHz, CDCl3) δ 2.30 (s, CH3), 3.65 (s, OCH3),
5.20 (s, 4-H), 6.80-8.23 (m, aromatic H) ppm; 13C NMR (75.5 MHz, CDCl3) δ 21.65 (CH3) 55.57 (OCH3)
66.66 (C-4), 90.58 (C-5,4’), 115.07-161.41 (C-3 and aromatic C), 164.33 (C-1), 172.13 (C-2) ppm. Anal.
Calcd for C31H24N2O4: C, 76.21; H, 4.95; N, 5.73. Found: C, 76.15 ; H, 4.86; N, 5.82.
(5R*,4:4’R*)-Spiro[5-(p-anisyl)-3-(p-tolyl)isoxazoline-4,4’-(2’-phenyl)isoquinoline-1’,3’-dione] (4cf):
Yield (21%); orange solid; Mp 195 °C; 1H NMR (300 MHz, CDCl3) δ 2.24 (s, CH3), 3.78 (s, OCH3), 6.12
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(s, 5-H), 6.55-8.02 (m, aromatic H) ppm; C NMR (75.5 MHz, CDCl3) δ 21.78 (CH3), 55.82 (OCH3),
96.87 (C-5),70.85 (C-4,4’), 114.33-161.58 (C-3 and aromatic C), 163.66 (C=O), 171.57 (C=O) ppm.