Med Chem Res
12.54 (s, 1H, H–NH), 8.41(s, 1H, CH=NAr), 8.04–8.02 (m,
2H, H-300, 600), 8.02 (d, 2H, J = 8 Hz, H-20,60), 7.65 (t, 1H,
J = 7.6 Hz, H-400), 7.48 (t, 2H, J = 7.2 Hz, H-500), 7.38 (t,
1H, J = 7.2 Hz, H-30,50), 7.39 (s, 1H, H-5); 13C-NMR
(DMSO-d6, 75 MHz): d 172.1 (C, C-2), 150.9 (C, C-4),
148.2 (C, C-200), 142.8 (C=N), 136.1 (C, C-500), 133.4 (C,
C-10), 132.3 (CH, C-400), 130.8 (CH, C-600), 130.4 (CH,
C-30, C-50), 129.4 (CH, C-40), 129.2 (C, C-100), 128.2 (CH,
C-20, C-60), 123.2 (CH, C-300), 105.7 (CH, C-5); EI MS: m/z
(rel. abund. %), 324 (M?, 58.5), 176 (100), 134 (100), 102
(36), 77 (21); 65 (8.4). Anal. Calcd for C16H12N4O2S;
(324.36); C, 59.25; H, 3.73; N, 17.27; O, 9.87; S, 9.89;
Found; C, 59.27; H, 3.75; N, 17.25; O, 9.85; S, 9.91.
J = 7.6 Hz, H-40); 13C-NMR (DMSO-d6, 75 MHz): d
171.8 (C, C-2), 150.1 (C, C-4), 143.4 (C=N), 134.2 (C,
C-300), 133.1 (C, C-10), 131.4 (CH, C-400), 130.2 (CH, C-30,
C-50), 130.1 (CH, C-500), 128.9 (CH, C-40), 127.5 (CH,
C-600), 127.3 (CH, C-20, C-60), 127.2 (CH, C-200), 121.1 (C,
C-100), 105.2 (CH, C-5); EI MS: m/z (rel. abund. %), 313
(M?, 25.1), 233 (91.3), 191 (100), 174 (70.3), 134 (93.6);
91(40.3), 43 (40.8). Anal. Calcd for C16H12ClN3S;
(313.04); C, 61.24; H, 3.85; Cl, 11.30; N, 13.39; S, 10.22;
Found; C, 61.22; H, 3.87; Cl, 11.28; N, 13.41; S, 10.20.
(E)-2-(2-(4-Chlorobenzylidene)hydrazinyl)-4-phenylthiazole
1
(9) Yield: (79 %); H-NMR (300 M Hz, DMSO-d6): d
12.25 (s, 1H, H–NH), 8.01 (s, 1H, CH=NAr), 7.84 (d, 2H,
J = 7.5 Hz, H-20,60), 7.66 (d, 2H, J = 8.7 Hz, H-200,600),
7.48 (d, 2H, J = 8.4 Hz, H-300,500) 7.40 (t, 2H, J = 7.2 Hz,
H-30,50), 7.31 (t, 1H, J = 7.8 Hz, H-40), 7.26 (s, 1H, H-5);
13C-NMR (DMSO-d6, 75 MHz): d 171.8 (C, C-2), 150.4
(C, C-4), 143.5 (C=N), 136.8 (CH, C-400), 135.1 (C, C-100),
133.1 (C, C-10), 130.4 (C, C-200, C-600), 129.5 (CH, C-30,
C-50), 129.1 (C, C-300, C-500), 128.9 (CH, C-40), 127.7 (CH,
C-20, C-60), 105.3 (CH, C-5); EI MS: m/z (rel. abund. %),
311 (M?, 23.0), 294 (7.9), 176 (100), 134 (66.3). Anal.
Calcd for C16H12ClN3S; (313.04); C, 61.24; H, 3.85; Cl,
11.30; N, 13.39; S, 10.22; Found; C, 61.26; H, 3.83; Cl,
11.28; N, 13.37; S, 10.24.
(E)-2-(2-(3-Nitrobenzylidene)hydrazinyl)-4-phenylthiazole
(6) Yield: (89 %); 1H-NMR (300 MHz, DMSO-d6): d
12.47 (s, 1H, H–NH), 8.46 (s, 1H, CH=NAr), 8.19 (dd, 1H,
J1 ,2 = 2 Hz, J1 ,3 = 8 Hz, H-300), 8.19 (s, 1H, H-200),
8.08 (d, 1H, J = 8 Hz, H-600), 7.85 (d, 2H, J = 7.6 Hz,
H-20,60), 7.71 (t, 1H, J = 7.6 Hz, H-500), 7.40 (t, 2H,
J = 7.6 Hz, H-30,50), 7.38 (s, 1H, H-5), 7.30 (t, 1H,
J = 7.2 Hz, H-40); 13C-NMR (DMSO-d6, 75 MHz): d
172.2 (C, C-2), 150.5 (C, C-4), 148.2 (C, C-300), 143.1
(C=N), 134.9 (C, C-100), 133.4 (C, C-10), 132.3 (CH, C-600),
130.2 (CH, C-30, C-50), 130.1 (CH, C-500), 129.1 (CH,
C-40), 128.1 (CH, C-20, C-60), 126.8 (CH, C-400), 121.4
(CH, C-200), 105.3 (CH, C-5); EI MS: m/z (rel. abund. %),
324 (M?, 35.1), 176 (100), 134 (89.9), 104 (12.3), 77 (19);
63 (5). Anal. Calcd for C16H12N4O2S; (324.36); C, 59.25;
H, 3.73; N, 17.27; O, 9.87; S, 9.89; Found; C, 59.27; H,
3.75; N, 17.25; O, 9.85; S, 9.91.
00 00
00 00
(E)-2-(2-(2,4-Dichlorobenzylidene)hydrazinyl)-4-phenylth-
1
iazole (10) Yield: (76 %); H-NMR (300 MHz, DMSO-
d6): d 12.47 (s, 1H, H–NH), 8.26 (s, 1H, CH=NAr), 7.84 (d,
2H, J = 7.2 Hz, H-20,60), 7.56 (s, 1H, H-300), 7.53 (s, 1H,
H-5), 7.42–7.29 (m, 5H, H-30,50,40, 500,600); 13C-NMR
(DMSO-d6, 75 MHz): d 171.8 (C, C-2), 150.1 (C, C-4),
143.5 (C=N), 133.1 (C, C-10), 131.2 (C, C-200), 129.6 (CH,
C-30, C-50), 129.4 (CH, C-300), 129.2 (CH, C-600), 128.8
(CH, C-40), 128.5 (C, C-400), 127.7 (CH, C-20, C-60), 127.1
(CH, C-500), 121.1 (C, C-100), 105.2 (CH, C-5); EI MS: m/z
(rel. abund. %), 347 (M?, 3.37), 176 (100), 134 (92.1), 45
(28.5). Anal. Calcd for C16H11Cl2N3S; (347.01); C, 55.18;
H, 3.18; Cl, 20.36; N, 12.07; S, 9.21; Found; C, 55.16; H,
3.16; Cl, 20.34; N, 12.05; S, 9.23.
(E)-2-(2-(4-Nitrobenzylidene)hydrazinyl)-4-phenylthiazole
(7) Yield: (91 %); 1H-NMR (300 MHz, DMSO-d6): d
10.47 (s, 1H, H-NH), 8.21 (d, 2H, J = 8.8 Hz, H-20,60),
7.79 (d, 2H, J = 7.6 Hz, H-300,500), 7.66 (d, 2H,
J = 8.8 Hz, H-200,600), 7.26 (s, 1H, CH = NAr), 7.40 (t,
2H, J = 7.6 Hz, H-30, 50), 7.33-7.31 (m, 1H, H-40), 6.92 (s,
1H, H-5); 13C-NMR (DMSO-d6, 75 MHz): d 171.9 (C,
C-2), 150.6 (C, C-400), 150.5 (C, C-4), 143.1 (C=N), 140.1
(C, C-100), 133.1 (C, C-10), 129.3 (CH, C-30, C-50), 128.9
(CH, C-40), 127.2 (CH, C-20, C-60), 124.4 (CH, C-200, C-600),
124.1 (C, C-300, C-500), 105.1 (CH, C-5); EI MS: m/z (rel.
abund. %), 324 (M?, 90.6), 176 (100), 134 (65.2), 104
(7.7), 77 (6.2); 44 (24.9). Anal. Calcd for C16H12N4O2S;
(324.36); C, 59.25; H, 3.73; N, 17.27; O, 9.87; S, 9.89;
Found; C, 59.23; H, 3.71; N, 17.23; O, 9.89; S, 9.87.
(E)-2-(2-(2,6-Dichlorobenzylidene)hydrazinyl)-4-phenyl
thiazole (11) Yield: (88 %); 1H-NMR (400 MHz,
DMSO-d6): d 12.20 (s, 1H, H–NH), 8.26 (s, 1H, CH=NAr),
7.85 (d, 2H, J = 7.2 Hz, H-20,60), 7.54 (d, 2H, J = 8.4 Hz,
H-300,500), 7.42–7.36 (m, 3H, H-30,50,400), 7.32 (s, 1H, H-5),
7.32-7.29 (m, 3H, H-40); 13C-NMR (DMSO-d6, 75 MHz):
d 171.6 (C, C-2), 150.1 (C, C-4), 143.2 (C = N), 133.8 (C,
C-200, C-600), 133.1 (C, C-10), 130.2 (C, C-100), 129.4 (CH,
C-30, C-50), 129.2 (CH, C-400), 128.9 (CH, C-40), 128.4
(CH, C-300, C-500), 127.4 (CH, C-20, C-60), 105.0 (CH, C-5);
EI MS: m/z (rel. abund. %), 348 (M?,1.2), 176 (100), 148
(71.6), 89 (1.5). Anal. Calcd for C16H11Cl2N3S; (347.01);
(E)-2-(2-(3-Chlorobenzylidene)hydrazinyl)-4-phenylthiazole
(8) Yield: (85 %); 1H-NMR (400 MHz, DMSO-d6): d
12.28 (s, 1H, H–NH), 8.01 (s, 1H, CH=NAr), 7.84 (d, 2H,
J = 7.2 Hz, H-20,60), 7.68 (s, 1H, H-200), 7.60 (d, 1H,
J = 7.2 Hz, H-400), 7.47–7.42 (m, 3H, H-30,50,500), 7.39 (d,
1H, J = 7.6 Hz, H-600), 7.34 (s, 1H, H-5), 7.29 (t, 1H,
123