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H. M. E. Hassaneen – R. M. Pagni · Synthesis of New 3-Substituted Indole Derivatives
cm−1. – 1H NMR ([D6]DMSO): δ = 1.34 (t, 3H, J= 7.2 Hz, (0.2 mL) were added. The reaction mixture was heated un-
ester-CH3), 2.24 (s, 3H, thiazole-CH3), 2.43 (s, 3H, indole- der reflux for 2 h. The product formed was filtered and re-
CH3), 4.35 (q, 2H, J = 7.2 Hz, ester-CH2) 6.99 – 7.65 (m, 9H, crystallized from DMF to give pale-yellow crystals; m. p.
Ar H), 11.45 (s, 1H, NH). – 13C NMR ([D6]DMSO): δ = 231 ◦C; 82 % yield. – IR (KBr): ν = 1650 (C=O), 2195 (CN),
13.53, 13.67, 14.12, 61.25, 80.02, 110.67, 112.68, 116.03, 3185 (NH) cm−1. – 1H NMR ([D6]DMSO): δ = 2.51 (s,
119.67, 120.93, 121.02, 126.54, 128.88, 129.73, 131.0, 3H, indole-CH3), 3.22 (t, 2H, S-CH2), 4.11 (t, 2H, CH2-N),
134.66, 136.22, 138.85, 147.53, 153.98, 161.21. 165.10, 6.97 – 7.93 (m, 9H, Ar H), 11.03 (s, 1H, NH). – MS: m/z (%)
184.05. – Anal. for C25H21N3O3S: calcd. C 67.70, H 4.77, = 359 (11) [M]+. – Anal. for C21H17N3OS: calcd. C 70.17,
N 9.47, S 7.23; found C 67.64, H 4.71, N 9.37, S 7.18.
H 4.77, N 11.69, S 8.92; found C 70.11, H 4.69, N 11.62,
S 8.88.
3-(2-Methyl-1H-indol-3-yl)-2-(4-(2-oxo-chromen-3(2H)-yl)-
3-phenyl)-thiazole-2(3H)-ylidene)-3-oxo-propionitrile (13)
Synthesis of 2-(benzothiazol-2(3H)-ylidene)-3-(2-methyl-
1H-indol-3-yl)-3-oxo-propionitrile (15)
◦
Yellow Crystals; m. p. 313 C; 77 % yield. – IR (KBr):
A solution of compound 3 (0.67 g, 2 mmol) in glacial
acetic acid (10 mL) was cooled to 0 ◦C. A solution of
bromine (0.32 g, 4 mmol) in glacial acetic acid (5 mL) was
added dropwise during 10 min, followed by stirring for 6 h.
The product was obtained after adding ice-cold water. It
ν = 1650 (C=O), 1686 (C=O), 2191 (CN), 3313 (NH)
cm−1. – 1H NMR ([D6]DMSO): δ = 2.60 (s, 3H, indole-
CH3), 7.09 – 8.0 (m, 14H, Ar H), 8.34 (s, 1H, thiazole-
CH), 11.38 (s, 1H, NH). – 13C NMR ([D6]DMSO). – δ =
13.69, 84.99, 109.88, 110.90, 112.45, 113.87, 115.60, 116.0,
118.0, 119.94, 120.11, 120.7, 121.5, 124.99, 125.99, 129.39, was filtered, and recrystallized from DMF to give yellow
◦
crystals; m. p. 333 C; 62 % yield. – IR (KBr): ν = 1661
133.01, 134.77, 138.14, 140.68, 144.69, 152.45, 156.71,
(C=O), 2193 (CN), 3076 (NH), 3284 (NH) cm−1. – 1H NMR
181.87, 182.56. – MS: m/z (%) = 501 (11) [M]+. – Anal.
for C30H19N3O3S: calcd. C 71.84, H 3.82, N 8.38, S 6.39; ([D6]DMSO): δ = 2.49 (s, 3H, indole-CH3), 7.37 – 8.04 (m,
8H, Ar H), 10.11 (s, 1H, NH), 11.32 (s, 1H, NH). – 13C NMR
([D6]DMSO): δ = 13.49, 79.10, 113.69, 114.28, 115.14,
119.02, 122.34, 124.28, 124.55, 126.54, 126.90, 127.47,
129.01, 134.68, 135.16, 138.69, 167.48, 179.87, 182.66. –
Anal. for C19H13N3OS: calcd. C 68.86, H 3.95, N 12.68,
S 9.68; found C 68.79, H 3.90, N 12.56, S 9.57.
found C 71.77, H 3.76, N 8.29, S 6.33.
Synthesis of 3-(2-methyl-1H-indol-3-yl)-2-(-3-phenyl-thiaz-
olidin-2-ylidene)-3-oxo-propionitrile (14)
To a suspension of 3 (0.67 g, 2 mmol) in absolute ethanol
(10 mL), dibromoethane (0.38 g, 2 mmol) and triethylamine
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