1012
Med Chem Res (2014) 23:1004–1015
thiazole H), 7.8 (s, 1H, NH), 8.4 (s, 1H, -N=CH); 13C NMR
(DMSO-d6) d (ppm): 101.3 (thiazole-C-5), 115.5, 129.0
(Ar–CH), 143.1 (HC=N), 148.7 (thiazole-C-4), 151, 155.4,
160.0 (Ar–C-OCH3), 172.2 (thiazole-C-2); MS (m/z, %):
370 (M?1, 100); % elemental analysis found (calc.) for
C19H19N3O3S: C, 61.70 (61.77); H, 5.17 (5.18); N, 11.39
(11.37).
2k. 1-(2-fluorobenzylidene)-2-(4-phenylthiazol-2-
yl)hydrazine
M.P. 191–192 °C; yield: 81 %; Rf: 0.7 (chloroform:meth-
anol, 9:1); solubility: ethanol, methanol, DMSO, DMF; IR
(KBr, mmax cm-1): 3157 (-NH), 1607 (C=N azomethine),
1549 (aromatic C=C); 1H NMR (DMSO-d6) d (ppm):
6.5–7.5 (m, 9H, ArH), 7.9 (s, 1H, -N=CH), 9.6 (s, 1H,
thiazole H), 10.5 (s, 1H, NH); 13C NMR (DMSO-d6) d
(ppm): 43.3, 51.2, 109.4 (thiazole-C-5), 116.4, 128.5 (Ar–
CH), 145.1 (HC=N), 148.7 (thiazole-C-4), 155.4, 172.1
(thiazole-C-2); MS (m/z, %): 298 (M?1, 100). % elemental
analysis found (calc.) for C16H12FN3S: C, 64.69 (64.63); H,
4.08 (4.07); N, 14.15 (14.13).
2o. 1-(2,4-dihydroxybenzylidene)-2-(4-
trifluoromethylphenylthiazol-2-yl)hydrazine
M.P. 97–98 °C; yield: 69 %; Rf: 0.5 (chloroform:methanol,
9:1); solubility: ethanol, methanol, DMSO, DMF; IR (KBr,
mmax cm-1): 3448 (-OH, br.), 3271 (-NH), 1602 (C=N
azomethine), 1452 (aromatic C=C), 1250; 1H NMR
(DMSO-d6, 300 MHz) d (ppm): 7.2 (s, 1H, -N=CH),
7.3–7.6 (m, 7H, Ar–H), 8.0 (s, 1H, NH), 9.7 (s, 1H, o-OH);
13C NMR (DMSO-d6) d (ppm): 103.6 (thiazole-C-5),
122–139 (Ar–CH), 143.4 (HC=N), 148.4 (thiazole-C-4),
153 (Ar–C–OH), 170 (thiazole-C-2); MS (m/z, %): 380
(M?1, 100); % elemental analysis found (calc.) for
C17H12F3N3O2S: C, 53.93 (53.82); H, 3.20 (3.19); N, 11.18
(11.08).
2l. 1-(2,4-dihydroxybenzylidene)-2-(4-phenylthiazol-2-
yl)hydrazine
M.P. 81–82 °C; yield: 72 %; Rf: 0.65 (chloroform:metha-
nol, 9:1); solubility: ethanol, methanol, DMSO, DMF; IR
(KBr, mmax cm-1): 3420 (-OH, br.), 2924 (-NH), 1635
1
(C=N azomethine), 1566 (aromatic C=C), 1075; H NMR
(DMSO-d6, 300 MHz) d (ppm): 7.2–8.0 (m, 8H, ArH), 8.2
(s, 1H, NH), 9.9 (s, 1H, -N=CH), 12.1 (s, 1H, o-OH); 13C
NMR (DMSO-d6) d (ppm): 103.6 (thiazole-C-5), 122–139
(Ar–CH), 143.4 (HC=N), 148.4 (thiazole-C-4), 153 (Ar–C–
OH), 170 (thiazole-C-2); MS (m/z, %): 311 (M?, 100). %
elemental analysis found (calc.) for C16H13N3O2S: C,
61.82 (61.72); H, 4.23 (4.21); N, 13.52 (13.50).
2p. 1-(2-fluorobenzylidene)-2-(4-(4-chlorophenyl)thiazol-
2-yl)hydrazine
M.P. 190–191 °C; yield: 73 %; Rf: 0.7 (chloroform:meth-
anol, 9:1); solubility: chloroform, methanol, DMSO, DMF;
IR (KBr, mmax cm-1): 3069 (-NH), 1620 (C=N azome-
thine), 1581 (aromatic C=C), 918, 821, 752; 1H NMR
(DMSO-d6, 300 MHz) d (ppm): 7.0–7.2 (m, 4H, o-fluoro-
phenyl), 7.3 (d, 2H, p-chlorophenyl), 7.6 (d, 2H, p-chlo-
rophenyl), 7.7 (s, 1H, thiazole H), 7.8 (s, 1H, NH), 8.5 (s,
1H, -N=CH); 13C NMR (DMSO-d6) d (ppm): 100.3 (thia-
zole-C-5), 116.3, 118, 124.6, 129.3 (Ar–CH), 133.1
(HC=N), 143 (thiazole-C-4), 148, 161.1 (thiazole-C-2); MS
(m/z, %): 332 (M?1, 100), 333 (M?2, 36); % elemental
analysis found (calc.) for C16H11ClFN3S: C, 58.02 (57.92);
H, 3.35 (3.34); N, 12.69 (12.66).
2m. 1-(4-nitrobenzylidene)-2-(4-phenylthiazol-2-
yl)hydrazine
M.P. 104–105 °C; yield: 80 %; Rf: 0.5 (chloroform:meth-
anol, 9:1); solubility: chloroform, DMSO, DMF; IR (KBr,
mmax cm-1): 3120 (-NH), 1622 (C=N, azomethine), 1516
1
(aromatic C=C), 927, 849, 787; H NMR (DMSO-d6) d
(ppm): 7.1–7.6 (m, 9H, Ar–H), 7.7 (s, 1H, thiazole H), 7.8
(s, 1H, NH), 8.4 (s, 1H, -N=CH); 13C NMR (DMSO-d6) d
(ppm): 105.3 (thiazole-C-5), 115.7, 126.2, 129.0 (Ar–CH),
141.1 (HC=N), 148.0 (thiazole-C-4), 167.1 (thiazole-C-2);
MS (m/z, %): 325 (M?1, 100), 326 (M?2, 35). % ele-
mental analysis found (calc.) for C16H12N4O2S: C, 59.40
(59.25); H, 3.75 (3.73); N, 17.29 (17.27).
2q. 1-(3,4,5-trimethoxybenzylidene)-2-(4-(4-
chlorophenyl)thiazol-2-yl)hydrazine
M.P. 244–245 °C; yield: 65 %; Rf: 0.5 (chloroform:meth-
anol, 9:1); solubility: ethanol, methanol, DMSO, DMF; IR
(KBr, mmax cm-1): 3324 (-NH), 1620 (C=N azomethine),
1508 (aromatic C=C), 831, 748; 1H NMR (DMSO-d6,
300 MHz) d (ppm): 6.6–7.3 (m, 6H, ArH), 7.7 (s, 1H,
thiazole H), 7.8 (s, 1H, NH), 8.4 (s, 1H, -N=CH); 13C NMR
(DMSO-d6) d (ppm): 101.3 (thiazole-C-5), 115.5, 129.0
(Ar–CH), 143.1 (HC=N), 148.7 (thiazole-C-4), 151, 155.4,
160.0 (Ar–C-OCH3), 172.2 (thiazole-C-2); MS (m/z, %):
2n. 1-(3,4,5-trimethoxybenzylidene)-2-(4-phenylthiazol-2-
yl)hydrazine
M.P. 224–225 °C; yield: 64 %; Rf: 0.6 (chloroform:meth-
anol, 9:1); solubility: ethanol, methanol, DMSO, DMF; IR
(KBr, mmax cm-1): 3324 (-NH), 1620 (C=N azomethine),
1
1508 (aromatic C=C), 831 and 748; H NMR (DMSO-d6,
300 MHz) d (ppm): 6.5–7.3 (m, 7H, ArH), 7.7 (s, 1H,
123