568
A. A. Hassan et al.
Arch. Pharm. Chem. Life Sci. 2013, 346, 562–570
(E)-4-(4-Biphenyl-4-yl)-2-[2-(1-phenylethylidene)hydra-
(Z)-3-Benzyl-4-phenyl-2-[(E)-(1-phenylethylidene)hydra-
zinyl]thiazole (5g): Colorless crystals (0.310 g, 84%), mp 258–
zono]-2,3-dihydro-thiazole (6b): Colorless crystals (0.337 g,
–
–
260°C (ethanol); IR (KBr): n ¼ 3295 (NH), 1635 (C N), 1600,
88%), mp 278–280°C (ethanol); IR (KBr): n ¼ 1625 (C N), 1600,
–
–
1585 cmꢀ1 (Ar-C C); 1H NMR (DMSO-d6): dH ¼ 2.22 (s, 3H, CH3),
1585 cmꢀ1 (Ar-C C); 1H NMR (DMSO-d6): dH ¼ 2.38 (s, 3H, CH3),
–
–
–
–
7.28 (d, J ¼ 8.20, 2H, Ar-H-o’), 7.34 (s, 1H, thiazole-CH), 7.37 (t,
J ¼ 7.10, 1H, Ar-H-p”’), 7.46 (t, J ¼ 7.6, 2H, Ar-H-m”’), 7.54 (d,
J ¼ 7.0, 2H, Ar-H-o”’), 7.55 (d, J ¼ 6.8, 2H, Ar-H-m”), 7.57 (t, J ¼ 7.3,
3H, Ar-H-m’,p’), 7.61 (d, J ¼ 7.8, 2H, Ar-H-o”), 11.26 (br, s, 1H, NH);
13C NMR (DMSO-d6): dC ¼ 14.77 (CH3), 106.33 (thiazole-CH), 126.74
(C-m’), 126.96 (C-o”’), 127.68 (C-p”’), 127.76 (C-p”), 128.09 (C-i’),
128.78 (C-m”’), 129.13 (C-m”), 129.51 (C-o’), 130.33 (C-o”), 131.65 (C-
p’), 136.58 (C-i”), 139.34 (C-i”’), 144.87 (thiazoleþ-C-4), 159.61 (acyclic-
–
4.89 (s, 2H, CH2), 6.99 (s, 1H, thiazole-CH), 7.22–7.45 (m, 6H, Ar-
CH), 7.55–7.78 ppm (m, 9H, Ar-CH); 13C NMR (DMSO-d6):
dC ¼ 14.44 (CH3), 42.51 (CH2), 105.28 (thiazole-CH), 126.12,
126.44, 127.28, 127.66, 128.23, 128.31, 128.25, 128.53, 129.28
(Ar-CH), 131.42, 137.88, 139.16 (Ar-C), 141.89 (thiazole-C-4), 158.68
þ
–
(acyclic-C N), 162.94 ppm (thiazole-C-2); MS (EI): m/z 383 (M ,
–
100), 306 (25), 257 (18), 118 (36), 77 (86). Anal. calcd. for C24H21N3S
(383.51): C, 75.16; H, 5.52; N, 10.96; S, 8.36. Found: C, 74.99; H, 5.44;
N, 11.03; S, 8.52.
C N), 163.48 (thiazole-C-2);MS (EI): m/z 369 (M ), 210 (15), 152 (20),
–
118 (36), 97 (42), 77 (100). Anal. calcd. for C23H19N3S (369.48): C,
74.77; H, 5.18; N, 11.37; S, 8.68. Found: C, 74.61; H, 5.30; N, 11.24; S,
8.75.
(Z)-3-Allyl-4-phenyl-2-[(E)-(1-phenylethylidene)hydra-
zono]-2,3-dihydro-thiazole (6c): Colorless crystals (0.233 g,
70%), mp 246–248°C (ethanol); IR (KBr): n ¼ 2195 (Ali-H), 1635
ꢀ1
(Ar-C C); 1H NMR (DMSO-d6): dH
(E)-4-(4-Biphenyl-4-yl)-2-[2-(1-furan-2-yl)ethylidene)-
–
(C N), 1605, 1585 cm
–
–
–
hydrazineyl]thiazole (5h): Pale brown crystals (0.284 g, 79%),
¼ 2.31 (s, 3H, CH3), 4.49 (br, 2H, allyl-CH2N), 5.11–5.28 (m, 2H,
–
–
mp 210–212°C (ethanol); IR (KBr): n ¼ 3290 (NH), 1633 (C N),
allyl-CH2 ), 5.60–5.78 (m, 1H, allyl-CH¼), 7.12 (s, 1H, thiazole-
–
–
1
1600, 1585 cmꢀ1 (Ar-C C); H NMR (DMSO-d ): d ¼ 2.34 (s, 3H,
CH), 7.21–7.34 (m, 6H, Ar-CH), 7.44–7.54 (m, 4H, Ar-CH); 13C
NMR (DMSO-d6): dC ¼ 14.44 (CH3), 45.77 (allyl-CH2N), 106.18
(thiazole-CH), 116.71 (allyl-CH2¼), 126.69, 127.77, 128.21,
128.87, 129.21, 130.22 (Ar-CH), 131.54, 137.88 (Ar-C), 135.71
–
–
6
H
CH3), 6.11 (m, 1H, furan-CH), 6.87 (m, 2H, furan-CH, thiazole-CH),
7.22 (m, 1H, furan-CH), 7.24–7.89 (m, 9H, Ar-CH), 11.76 ppm (br s,
1H, NH); 13C NMR (DMSO-d6): dC ¼ 14.94 (CH3), 106.12 (thiazole-
CH), 111.12, 112.45 (furan-CH), 126.35, 127.77, 128.26, 129.35,
130.85 (Ar-CH), 136.61, 139.22, 141.18 (Ar-C), 141.08 (furan-CH),
–
–
–
(allyl-CH ), 142.19 (thiazole-C-4), 158.89 (acyclic-C N),
–
–
162.98 ppm (thiazole-C-2); MS (EI): m/z 333 (Mþ, 100), 256
(22), 232 (28), 118 (62), 77 (56). Anal. calcd. for C20H19N3S
(333.45): C, 72.04; H, 5.74; N, 12.60; S, 9.62. Found: C, 71.96; H,
5.82; N, 12.71; S, 9.76.
142.22 (thiazole-C-4), 151.12 (furan-C), 159.08 (acyclic-C N),
–
163.11 ppm (thiazole-C-2); MS (EI): m/z 359 (Mþ, 37), 206 (16),
344 (24), 97 (62), 94 (14), 77 (100). Anal. calcd. for C21H17N3OS
(359.44): C, 70.17; H, 4.77; N, 11.69; S, 8.92. Found: C, 69.98; H, 4.69;
N, 11.85; S, 8.88.
(Z)-3-Phenyl-4-(4-bromophenyl)-2-[(E)-(1-phenylethyli-
dene)hydrazono]-2,3-dihydrothiazole (6d): Colorless crys-
tals (0.345 g, 77%), mp 123–125°C (ethanol); IR ꢀ(K1Br): n ¼ 3110
(E)-4-(4-Biphenyl-4-yl)-2-[2-(1-pyridin-3-yl)ethylidene)-
(Ar-H), 2285 (Ali-H), 1635 (C N), 1600, 1565 cm (Ar-C C); 1H
–
–
–
–
hydrazineyl]thiazole (5i): Yellow crystals (0.244 g, 66%), mp
–
278–280°C (ethanol); IR (KBr): n ¼ 3285 (NH), 1630 (C N), 1600,
NMR (DMSO-d6): dH ¼ 2.51 (s, 3H, CH3), 6.69–7.02 (m, 4H, Ar-CH),
7.18 (s, 1H, thiazole-CH), 7.22–7.86 (m, 5H, Ar-CH), 7.88–8.02
ppm (m, 5H, Ar-CH); 13C NMR (DMSO-d6): dC ¼ 14.43 (CH3), 106.08
(thiazole-CH), 126.11 (Ar-C-Br), 126.61, 127.47, 128.92, 128.55,
128.74, 129.51, 130.66, 134.22 (Ar-CH), 137.94, 138.76, 141.23
–
1590 cmꢀ1 (Ar-C C); 1H NMR (DMSO-d6): dH ¼ 2.45 (s, 3H, CH3),
–
–
6.89–7.95 (m, 10H, Ar-CH, thiazole-CH), 7.99 (m, 1H, pyridin-CH),
8.11 (m, 1H, pyridin-CH), 8.28 (m, 1H, pyridin-CH), 9.02
(m, 1H, pyridin-CH), 11.99 ppm (br s, 1H, NH); 13C NMR
(DMSO-d6): dC ¼ 14.18 (CH3), 105.92 (thiazole-CH), 126.33,
127.86, 129.11, 130.68, 131.23 (Ar-CH), 131.55, 137.14, 139.77
(Ar-C), 142.69 (thiazole-C-4), 142.75 (pyridin-C), 142.78, 144.09,
–
–
(Ar-C), 142.29 (thiazole-C-4), 158.88 (acyclic-C N), 163.56 ppm
–
(thiazole-C-2); MS (EI): m/z 447/449 (Mþ, 100), 367 (16), 216 (33),
118 (62), 98 (14), 77 (34). Anal. calcd. for C23H18BrN3S (448.38): C,
61.61; H, 4.05; N, 9.37; S, 7.15. Found: C, 61.76; H, 4.15; N, 9.24; S,
7.28.
151.13, 152.45 (pyridine-CH), 159.52 (acyclic-C N), 163.68 ppm
–
(thiazole-C-2); MS (EI): m/z 370 (Mþ, 26), 217 (19), 153 (22), 192 (15),
178 (27), 97 (100) 77 (51). Anal. calcd. for C22H18N4S (370.47):
C, 71.32; H, 4.90; N, 15.12; S, 8.66. Found: C, 71.44; H, 5.08;
N, 15.26; S, 8.55.
(Z)-3-Benzyl-4-(4-bromophenyl)-2-[(E)-(1-phenylethyli-
dene)hydrazono]-2,3-dihydrothiazole (6e): Orange crystals
(0.374 g, 81%), mp 136–138°C (ꢀet1hanol); IR (KBr): n ¼ 2290 (Ali-
1
(Z)-3,4-Diphenyl-2-[(E)-(1-phenylethylidene)hydrazono]-
–
–
–
H), 1635 (C N), 1605, 1580 cm (Ar-C C); H NMR (DMSO-d ):
–
6
2,3-dihydrothiazole (6a): Colorless crystals (0.303 g, 82%), mp
dH ¼ 2.38 (s, 3H, CH3), 4.98 (s, 2H, CH2), 6.97–7.02 (m, 4H, Ar-
CH), 7.06 (s, 1H, thiazole-CH), 7.22–7.82 (m, 5H, Ar-CH), 7.86–
8.12 ppm (m, 5H, Ar-CH); 13C NMR (DMSO-d6): dC ¼ 13.98 (CH3),
42.44 (CH2), 105.98 (thiazole-CH), 125.23 (Ar-C-Br), 126.55,
127.68, 128.66, 128.99, 128.56, 128.25, 129.56, 131.38
(Ar-CH), 137.38, 139.16, 141.55 (Ar-C), 142.80 (thiazole-C-4),
–
461/463 (Mþ, 22), 370 (100), 306 (19), 154 (33), 118 (23),
91 (24), 77 (73). Anal. calcd. for C24H20BrN3S (462.40): C, 62.34; H,
4.36; N, 9.09; S, 6.93. Found: C, 62.51; H, 4.44; N, 8.93; S,
7.02.
ꢀ1
–
310–312°C (ethanol); IR (KBr): n ¼ 1630 (C N), 1600, 1585 cm
–
1
–
(Ar-C C); H NMR (DMSO-d ): d ¼ 2.49 (s, 3H, CH3), 7.23 (s, 1H,
–
6
H
thiazole-CH), 7.24–7.56 (m, 6H, Ar-CH), 7.66–7.82 ppm (m, 9H, Ar-
CH); 13C NMR (DMSO-d6): dC ¼ 14.50 (CH3), 105.28 (thiazole-CH),
126.02, 126.60, 127.07, 127.98, 128.11, 128.34, 128.55, 128.97,
129.21 (Ar-CH), 130.64, 137.94, 138.76 (Ar-C), 142.39 (thiazole-C-4),
159.18 (acyclic-C N), 163.14 ppm (thiazole-C-2); MS (EI): m/z
–
–
–
159.33 (acyclic-C N), 163.44 ppm (thiazole-C-2); MS (EI): m/z 369
(Mþ, 21), 292 (16), 174 (55), 118 (26), 77 (100). Anal. calcd. for
C23H19N3S (369.48): C, 74.77; H, 5.18; N, 11.37; S, 8.68. Found: C,
74.86; H, 5.06; N, 11.43; S, 8.51.
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