A simple and efficient procedure for synthesis of..., N. FOROUGHIFAR, et al.,
aromatic), 7.88-7.98 (m, 4H, aromatic), 8.80 (d, J = 4.2 Hz, 1H, aromatic), 9.00 (s, 1H, aromatic), 9.13 (s, 1H,
aromatic); 13 C-NMR (DMSO-d6 , δ, ppm): 32.8, 120.2, 123.9, 124.8, 131.9, 134.7, 135.3, 147.7, 153.1, 162.8,
163.3, 167.3; Anal. Calcd. for C16 H10 N4 O3 : C, 62.74; H, 3.29; N, 18.29. Found C, 62.44, H, 3.18, N, 18.18.
(S)-2-[1-(5-Pyridine-4-yl)-1,3,4-oxadiazole-2-yl) ethyl]isoindoline-1,3-dione (5c):
A) Yield: 50%; B) yield: 36%; mp 166-168 ◦ C; [α]D22 = -215 (c = 0.2, DMSO); IR (KBr) (ν cm−1): 3040, 2984,
1780 (C=O), 1714 (C=O), 1607 (C=N), 1514; 1 H-NMR (DMSO-d6 , δ, ppm): 1.89 (d, J = 7.1 Hz, 3H, CH3),
5.84 (q, J = 7.1 Hz, 1H, N-CH), 7.87-7.94 (m, 6H, aromatic), 8.79 (d, J = 5.0 Hz, 2H, aromatic); 13 C-NMR
(DMSO-d6 , δ, ppm): δ = 15.4, 47.8, 121.7, 123.5, 132.3, 134.9, 139.8, 150.9, 164.4, 167.8, 168.8; Anal. Calcd.
for C17 H12 N4 O3 : C, 63.75; H, 3.78; N, 17.49. Found C, 63.58, H, 3.69, N, 17.38.
(S)-2-[1-(5-Pyridine-3-yl)-1,3,4-oxadiazole-2-yl) ethyl]isoindoline-1,3-dione (5d):
A) Yield: 53%; B) yield: 35%; mp 147-149 ◦ C; [α]D22 = -180 (c = 0.2, CHCl3); IR (KBr) (ν cm−1): 3037,
2985, 17780 (C=O), 1712 (C=O), 1600 (C=N), 1527; 1 H-NMR (CDCl3 , δ, ppm): 2.05 (d, J = 7.2 Hz, 3H,
CH3), 5.79 (q, J = 7.1 Hz, 1H, N-CH), 7.59 (d, d, J = 7.2, 4.2 Hz, 1H, aromatic), 7.78-7.82 (m, 2H, aromatic),
7.88-7.92 (m, 2H, aromatic), 8.49 (d, J = 7.9 Hz, 1H, aromatic), 8.80 (s, 1H, aromatic), 9.23 (s, 1H, aromatic);
13 C-NMR (CDCl3 , δ, ppm): 16.2, 41.7, 120.3, 123.7, 123.9, 131.6, 134.5 (2C), 147.5, 152.1, 163.1, 165.1, 166.8;
Anal. Calcd. for C17 H12 N4 O3 : C, 63.75; H, 3.78; N, 17.49. Found C, 63.62, H, 3.76, N, 17.41.
(S)-2-[2-Phenyl-1-(5-pyridine-4-yl)-1,3,4-oxadiazole-2-yl)ethyl]isoindoline-1,3-dione
(5e):
A) Yield: 58%; B) yield: 37%; mp 156-157 ◦ C; [α]D22 = -320 (c = 0.2, DMSO); IR (KBr) (ν cm−1): 3053,
2924, 1772 (C=O), 1720 (C=O), 1608 (C=N), 1554, 1467 (C=C); 1 H-NMR (DMSO-d6 , δ, ppm): 3.71-3.80
(m, 2H, CH2), 6.05 (d, d, J = 10.3, 5.5 Hz, 1H, N-CH), 7.19-7.25 (m, 5H, aromatic), 7.85 (s, 4H, aromatic),
7.92 (d, J = 4.0 Hz, 2H, aromatic), 8.80 (d, J = 3.6 Hz, 2H, aromatic); 13 C-NMR (DMSO-d6 , δ, ppm): 34.8,
47.2, 120.7, 124.0, 127.5, 128.9, 129.5, 130.6, 131.1, 135.5, 136.4, 151.5, 163.5, 165.3, 167.2; Anal. Calcd. for
C23 H16 N4 O3 : C, 69.69; H, 4.07; N, 14.13. Found C, 69.44, H, 3.95, N, 14.05.
(S)-2-[2-Phenyl-1-(5-pyridine-3-yl)-1,3,4-oxadiazole-2-yl)ethyl]isoindoline-1,3-dione
(5f):
A) Yield: 54%; B) yield: 34%; mp 157-160 ◦ C; [α]D22 = -172 (c = 0.2, CHCl3); IR (KBr) (ν cm−1): 3044,
2932, 1776 (C=O), 1720 (C=O), 1601 (C=N), 1550, 1456 (C=C), 1 H-NMR (CDCl3 , δ, ppm): 3.73-3.89 (m,
2H, CH2), 5.95 (d, d, J = 10.3, 5.5 Hz, 1H, N-CH), 7.12-7.27 (m, 5H, aromatic), 7.50 (d, d, J = 7.5, 4.9
Hz, 1H, aromatic), 7.72-7.85 (m, 4H, aromatic), 8.38 (d,J = 7.9 Hz, 1H, aromatic), 8.79 (s, 1H, aromatic), 9.22
(s, 1H, aromatic); 13 C-NMR (CDCl3 , δ, ppm): 35.6, 47.3, 120.1, 123.7 (2C), 127.3, 128.7, 129.1, 131.3, 134.3,
607