10
A. A. HASSAN ET AL.
(s, 3H, OCH3), 7.01–7.05 (m, H, Ar–H), 7.09–7.11 (m, 1H, Ar–H), 7.33 (s, 1H, thiazole-
CH), 7.35–7.41 (m, 2H, Ar–H), 7.43–7.45 (m, 2H, Ar–H), 7.81–7.86 (m, 3H, Ar–H), 8.44
(s, 1H, CH N), 11.05 (s, br, NH), 13C NMR (DMSO-d6): δ = 55.73 (OCH3), 103.78
=
C
(thiazole-CH), 122.17, 125.02, 125.72, 127.90, 128.36, 128.71 (Ar–CH), 131.06, 133.83
=
(Ar–C), 148.08 (CH N), 150.27 (thiazole-C5), 157.30 (Ar–C–O), 168.36 (thiazole-C2).
EI-mass, m/z (%) 309 (M+,10), 175 (35), 135 (79), 91 (39), 77 (100). Anal. Calcd. for
C17H15N3OS (309.39): C, 66.00; H, 4.89; N, 13.58; S, 10.36. Found: C, 65.84; H, 4.96; N,
13.66; S, 10.55.
(E)-2-[2-(3,4-Dimethoxybenzylidene)hydrazinyl]-4-phenylthiazole (3e)
Yellow crystals (ethanol), (0.328 g, 97%), m.p = 256–258°C. IR (KBr): υ = 3317 (NH),
1613 (C N), 1585 (Ar–C C), 1035,748 (C–S–C) cm−1. 1H NMR (DMSO-d6): δ = 3.80
=
=
H
(s, 3H, OCH3), 3.82 (s, 3H, OCH3), 7.00–7.03 (m,1H, Ar–H), 7.18–7.20 (m, 1H, Ar–H),
7.28–7.31 (m, 2H, Ar–H), 7.32 (s, 1H, thiazole-CH), 7.40–7.45 (m, 2H, Ar–H), 7.84–7.86
(m, 2H, Ar–H), 8.00 (s, 1H, CH N), 11.03 (s, br, 1H, NH). 13C NMR (DMSO-d6):
=
δ = 55.38, 55.58 (OCH3), 103.32 (thiazole-CH), 120.39, 125.59, 127.06, 127.69, 128.65
c
=
(Ar–CH), 131.22, 133.76 (Ar–C), 147.99 (CH N), 150.18 (thiazole-C5), 157.49, 158.12
(Ar–C–O), 168.35 (thiazole-C2). EI-mass, m/z (%): 339 (M+, 4), 175 (64), 135 (100), 106
(22), 77 (72). Anal. Calcd. for C18H17N3O2S (339.41): C, 63.70; H, 5.05; N, 12.38; S, 9.45.
Found: C, 63.86; H, 4.92; N, 12.26; S, 9.61.
(E)-2-[2-(Naphthalene-2-ylmethylene)hydrazinyl]-4-phenylthiazole (3f)
Yellow crystals (ethanol), (0.322 g, 98%),m.p. = 250–252°C, IR (KBr): υ = 3338 (NH),
−1
=
=
1619 (C N), 1608 (Ar–C C), 1037, 745 (C–S–C) cm
.
1H NMR (DMSO-d6):
δ
= 7.31, 7.34 (m, 1H, Ar–H), 7.39 (s, 1H, thiazole-CH), 7.41–7.43 (m, 1H, Ar–H),
H
7.44–7.46 (m, 2H, Ar–H), 7.61–7.63 (m, 2H, Ar–H), 7.69–7.72 (m, 2H, Ar–H), 7.88–7.90
=
(m, 1H, Ar–H), 7.99–8.01 (m, 1H, Ar–H), 8.71 (s, 1H, CH N), 8.73–8.78 (m, 2H, Ar-H),
11.0 (s, br, 1H, NH).13C NMR (DMSO-d6): δ = 103.84 (thiazole-CH), 125.62, 126.28,
C
127.29, 127.71, 128.68, 128.89, 129.91 (Ar–CH), 130.83, 132.66, 133.45 (Ar–C), 147.67
+
=
(CH N), 150.67 (thiazole-C5), 168.24 (thiazole-C2). EI-mass, m/z (%): 329 (M , 8), 175
(87), 135 (100), 82 (76), 77 (46). Anal. Calcd. for C20H15N3S (329.42): C, 72.92; H, 4.59;
N, 12.76; S, 9.73. Found: C, 73.11; H, 4.66; N, 12.69; S, 9.58.
(E)-2-[2-(Anthracen-2-ylmethylene)hydrzinyl]-4-phenylthiazole (3g)
Yellow crystals (ethanol), (0.363 g, 96%), m.p = 264–266°C, IR (KBr): υ = 3336 (NH),
−1
=
=
1621 (C N), 1591 (Ar C C), 1041, 749 (C–S–C) cm
.
1H NMR (DMSO-d6):
δ
= 7.27–7.30 (m, 4H, Ar–H), 7.33 (s, 1H, thiazole-CH), 7.57–7.60 (m, 2H, Ar–H),
H
7.68–7.70 (m,2H,Ar–H), 7.89–7.90 (m, 2H, Ar-H), 8.17–8.20 (m, 2H, Ar–H), 8.67 (s,
H, CH N), 8.70–8.74 (m, 2H, Ar-H), 10.97 (s, br, 1H, NH). 13C NMR (DMSO-d6):
=
δ = 103.84 (thiazole-CH), 125.80, 126.42, 127.20, 127.66, 127.88,128.24, 128.68, 128.84,
C
=
129.91 (Ar–CH), 130.83, 132.66, 133.45, 135.26 (Ar–C), 148.27 (CH N), 152.67 (thiazole-
C5), 168.88 (thiazole-C2). EI-mass, m/z (%): 379 (M+, 8), 19 (21), 134 (27), 77 (100). Anal.
Calcd. for C24H17N3S (379.48): C, 75.96; H, 4.52; N, 11.07; S, 8.45. Found: C, 76.13; H, 4.49;
N, 10.89; S, 8.38.