70
Aychiluhim and Rao
7.30–7.44 (m, 6H, Ar-H), 7.51–7.56 (m, 3H, Ar-H), 7.68–7.72 (m, 1H, Ar-H), 10.82 (s,
1H, N H).13C NMR (DMSO-d6): δ 22.99, 48.35, 109.30, 111.39, 116.11, 117.27, 118.00,
118.37, 121.01, 123.98, 124.33, 124.84, 126.87, 129.50, 130.25, 133.31, 135.97, 146.79,
153.59, 158.80.
Anal. Calcd. C28H21N3O2S: C, 72.55; H, 4.57; N, 9.06; S, 6.92. Found: C, 72.51; H,
4.54; N, 9.12; S, 6.98.
3-{(14E)-3-[2-(1H-Indol-3-yl)ethyl]-2-(4-chlorophenylimino)-2,3-dihydrothiazol-4-yl}-
2H-chromen-2-one(4b)
Pale yellow solid (from ethanol-DMF), mp. 259◦C–260◦C, 87% yield. IR (cm−1): 1568
(C N), 1725 (C O, lactone), 3215 (N H, indole); 1H NMR (DMSO-d6): δ 3.12 (t, 2H, J
= 6.2 Hz, -CH2- tryptamine), 4.26 (bs, 2H, -CH2-N tryptamine), 6.66 (t, 1H, J = 7.4 Hz,
Ar-H), 6.85 (t, 2H, J = 7.8 Hz, Ar-H), 7.06 (s, 1H, Ar-H), 7.19–7.22 (m, 2H, Ar-H),
7.31(d, 3H, J = 9.6 Hz, Ar-H), 7.41 (t, 2H, J = 7.3 Hz, Ar-H), 7.40–7.43 (m, 2H, Ar-H),
7.70 (t, 1H, J = 4.8 Hz, Ar-H), 7.69 (t, 1H, J = 7.8 Hz, Ar-H), 10.82 (s, 1H, -NH).13C
NMR (DMSO-d6): δ 22.99, 48.38, 109.36, 111.34, 116.03, 117.22, 117.96, 118.29, 120.93,
123.93, 124.76, 125.89, 126.82, 129.45, 130.06, 133.22, 135.91, 136.41, 146.62, 153.54,
158.72.
Anal. Calcd. for C28H20ClN3O2S: C, 67.53; H, 4.05; Cl, 7.12; N, 8.44; S, 6.44. Found:
C, 67.50; H, 4.12; N, 8.40; S, 6.40.
3-{(14E)-3-[2-(1H-Indol-3-yl)ethyl]2-(p-tolylimino)-2,3-dihydrothiazol-4-yl}-2H-
chromen-2-one(4c)
Pale yellow solid (from ethanol-DMF), mp. 261◦C–263◦C, 82% yield. IR (cm−1): 1569
(C N), 1718 (C O, lactone), 3236 (N H, indole); 1 H NMR (DMSO-d6): δ 2.37 (s, 3H,
-CH3), 3.13 (t, 2H, J = 6.2 Hz, -CH2- tryptamine), 4.39 (bs, 2H, -CH2-N tryptamine), 6.67
(t, 1H, J = 7.6 Hz, Ar-H), 6.86 (t, 1H, J = 7.9 Hz, Ar-H), 7.00 (s, 1H, Ar-H), 7.09 (d, 1H, J
= 2.0 Hz, Ar-H), 7.24 (t, 4H, J = 8.4 Hz, Ar-H), 7.33–7.44 (m, 5H, Ar-H), 7.56–7.58 (m,
1H, Ar-H), 7.69–7.73 (m, 1H, Ar-H), 10.88 (s, 1H, -NH).13C NMR (DMSO-d6): δ 20.61,
22.98, 48.51, 109.12, 111.35, 115.72, 116.05, 117.19, 117.94, 118.33, 120.95, 124.01,
124.53, 124.78, 126.81, 129.50, 130.65, 133.29, 135.92, 136.57, 146.84, 153.57, 158.72.
Anal. Calcd. for C29H23N3O2S: C, 72.93; H, 4.85; N, 8.80; S, 6.71. Found: C, 72.96;
H, 4.89; N, 8.73; S, 6.67.
3-{(14E)-3-[2-(1H-Indol-3-yl)ethyl]-2,3-dihydro-2-(phenylimino)thiazol-4-yl}-8-
methoxy -2H-chromen-2-one(4d)
Yellow solid (from ethanol), mp. 256◦C–258◦C, 86% yield. IR (cm−1): 1567 (C N), 1719
1
(C O, lactone), 3161 (N H, indole); H NMR (DMSO-d6): 3.13 (t, 2H, J = 6.0 Hz,
-CH2- tryptamine), 3.94 (s, 3H, OCH3), 4.36 (bs, 2H, -CH2-N tryptamine), 6.70 (t, 1H, J =
7.4 Hz, Ar-H), 6.86–6.94 (m, 2H, Ar-H), 7.07–7.12 (m, 2H, Ar-H), 7.22 (t, 2H, J = 7.6 Hz,
Ar-H), 7.33–7.40 (m, 6H, Ar-H), 7.54 (t, 2H, J = 7.8 Hz, Ar-H), 10.84 (s, 1H, N H).13C
NMR (DMSO-d6): δ 23.05, 48.59, 56.27, 109.18, 111.35, 115.50, 115.99, 117.22, 118.34,