Med Chem Res
68.05; H, 4.97; N, 10.35. Found: C, 68.36; H, 4.71; N,
10.06.
(m, 4H, H-6, H-7, H-50, H-400), 7.48 (d, 2H, J = 7.40 Hz,
H-300, H-500), 7.74 (d, 1H, J = 7.44 Hz, H-5), 7.99 (d, 2H,
J = 7.40 Hz, H-200, H-600), 8.84 (d, 1H, J = 7.48 Hz, H-8);
13C NMR (100 MHz, CDCl3): d = 13.91 (–CH2CH2CH3),
21.79 (–CH2CH2CH3), 27.70 (C-4), 28.54 (–CH2CH2CH3),
110.81 (C-50), 121.13 (C-8), 125.58 (C-7), 126.46 (C-200,
C-600), 128.67 (C-400), 128.74 (C-6), 128.80 (C-300, C-500),
129.01 (C-3a), 132.78 (C-100), 134.81 (C-5), 138.48 (C-8a),
141.59 (C-4a), 148.62 (C-8b), 153.35 (C-40), 154.57 (C-3),
159.62 (C-20); ESI–MS m/z: 358.6 [M ? 1]?; Anal. Calcd.
for C22H19N3S (357.13): C, 73.92; H, 5.36; N, 11.75.
Found: C, 73.65; H, 5.68; N, 11.37.
2-(3-Isobutylindeno[1,2-c]pyrazol-1(4H)-yl)-4-p-tolylthiazole
(4c) Offwhite solid; yield 57 %; mp 115–118 °C; IR
(KBr): mmax 742, 1020, 1067, 1460, 1529, 1530 (C = N),
2901, 2943 (aliphatic C–H stretch), 3049, 3121 (aromatic
C–H stretch) cm-1; 1H NMR (400 MHz, CDCl3): d = 0.99
(d, 6H, J = 6.40 Hz, –CH2CH(CH3)2), 2.02–2.09 (m, 1H,
–CH2CH(CH3)2), 2.43 (s, 3H, CH3), 2.61 (d, 2H,
J = 7.20 Hz, –CH2CH(CH3)2), 3.59 (s, 2H, H-4),
7.19–7.53 (m, 5H, H-6, H-7, H-50, H-300, H-500), 7.77 (d,
1H, J = 7.20 Hz, H-5), 7.88 (d, 2H, J = 8.40 Hz, H-200,
H-600), 8.85 (d, 1H, J = 7.60 Hz, H-8); 13C NMR
(100 MHz, CDCl3): d = 21.32 (CH3), 22.18 (–CH2
CH(CH3)2), 27.67 (C-4), 27.74 (–CH2CH(CH3)2), 36.20
(–CH2CH(CH3)2), 109.99 (C-50), 121.17 (C-8), 125.35 (C-
7), 126.09 (C-200, C-600), 128.89 (C-3a), 129.43 (C-6),
129.62 (C-300, C-500), 131.49 (C-100), 134.75 (C-5), 138.34
(C-400), 138.62 (C-8a), 141.49 (C-4a), 148.41 (C-8b),
153.51 (C-40), 154.43 (C-3), 159.51 (C-20); ESI–MS m/z:
386.2 [M ? 1]?, 387.3 [M ? 2]?, 408.2 [M ? Na]?;
Anal. Calcd. for C24H23N3S (385.16): C, 74.77; H, 6.01; N,
10.90; S, 8.32. Found: C, 74.46; H, 6.37; N, 10.68; S, 8.56.
4-(4-Chlorophenyl)-2-(3-propylindeno[1,2-c]pyrazol-1(4H)-
yl)thiazole (4f) Offwhite solid; yield 54 %; mp
116–118 °C; IR (KBr): mmax 727, 1082, 1472, 1512, 1539
(C = N), 2872, 2957 (aliphatic C–H stretch), 3051, 3128
(aromatic C–H stretch) cm-1
;
1H NMR (400 MHz,
CDCl3): d = 0.96 (t, 3H, –CH2CH2CH3), 1.70–1.80 (m,
2H, –CH2CH2CH3), 2.72 (t, 2H, –CH2CH2CH3), 3.58 (s,
2H, H-4), 7.24–7.33 (m, 3H, H-6, H-7, H-50), 7.47 (d, 2H,
J = 8.64 Hz, H-300, H-500), 7.73 (d, 1H, J = 7.40 Hz, H-5),
7.90 (d, 2H, J = 8.64 Hz, H-200, H-600), 8.77 (d, 1H,
J = 7.60 Hz, H-8); 13C NMR (100 MHz, CDCl3):
d = 13.90 (–CH2CH2CH3), 21.80 (–CH2CH2CH3), 27.71
(C-4), 28.56 (–CH2CH2CH3), 111.08 (C-50), 121.12 (C-8),
124.04 (C-7), 126.79 (C-200, C-600), 128.89 (C-3a), 129.27
(C-300, C-500), 129.99 (C-6), 132.53 (C-100), 132.81 (C-400),
134.87 (C-5), 138.87 (C-8a), 141.23 (C-4a), 148.65 (C-8b),
153.51 (C-40), 154.31 (C-3), 159.45 (C-20); ESI–MS m/z:
392.1 [M ? 1]?. Anal. Calcd. for C22H18ClN3S (391.09):
C, 67.42; H, 4.63; N, 10.72. Found: C, 67.73; H, 4.34; N,
10.46.
2-(3-Isobutylindeno[1,2-c]pyrazol-1(4H)-yl)-4-(4-methoxy
phenyl)thiazole (4d) Offwhite solid; yield 55 %; mp
120–122 °C; IR (KBr): mmax 735, 1036, 1070, 1466, 1514,
1543 (C = N), 2851, 2955 (aliphatic C–H stretch), 3055,
1
3117 (aromatic C–H stretch) cm-1; H NMR (400 MHz,
CDCl3): d = 1.02 (d, 6H, J = 6.80 Hz, –CH2CH(CH3)2),
2.11–2.18 (m, 1H, –CH2CH(CH3)2), 2.65 (d, 2H,
J = 7.60 Hz, –CH2CH(CH3)2), 3.62 (s, 2H, H-4), 3.89 (s,
3H, OCH3), 7.03 (2H, d, J = 8.80 Hz, H-300, H-500), 7.11 (s,
1H, H-50), 7.32–7.47 (m, 2H, H-6, H-7), 7.53 (d, 1H,
J = 7.60 Hz, H-5), 7.92 (d, 2H, J = 8.80 Hz, H-200, H-600),
8.83 (d, 1H, J = 7.60 Hz, H-8); 13C NMR (100 MHz,
CDCl3): d = 22.16 (–CH2CH(CH3)2), 27.71 (C-4), 27.78
(–CH2CH(CH3)2), 36.15(–CH2CH(CH3)2), 55.45 (OCH3),
108.97 (C-50), 114.25 (C-300, C-500), 121.13 (C-8), 124.38
(C-7), 127.08 (C-200, C-600), 127.53 (C-100), 129.07 (C-3a),
129.72 (C-6), 134.64 (C-5), 138.51 (C-8a), 141.84 (C-4a),
148.56 (C-8b), 153.22 (C-40), 154.37 (C-3), 159.95 (C-20),
159.95 (C-400); ESI–MS m/z: 402.0 [M ? 1]?; Anal. Calcd.
for C24H23N3OS (401.16): C, 71.79; H, 5.77; N, 10.47.
Found: C, 71.98; H, 5.42; N, 10.75.
2-(3-Propylindeno[1,2-c]pyrazol-1(4H)-yl)-4-p-tolylthiazole
(4g) Offwhite solid; yield 58 %; mp 117–120 °C; IR
(KBr): mmax 727, 1082, 1474, 1508, 1543 (C = N), 2872,
2957 (aliphatic C–H stretch), 3053, 3128 (aromatic C–H
1
stretch) cm-1; H NMR (400 MHz, CDCl3): d = 0.95 (t,
3H, –CH2CH2CH3), 1.69–1.79 (m, 2H, –CH2CH2CH3),
2.42 (s, 3H, CH3), 2.70 (t, 2H, –CH2CH2CH3), 3.57 (s, 2H,
H-4), 7.23–7.34 (m, 3H, H-6, H-7, H-50), 7.47 (d, 2H,
J = 8.24 Hz, H-300, H-500), 7.72 (d, 1H, J = 7.28 Hz, H-5),
8.04 (d, 2H, J = 8.24 Hz, H-200, H-600), 8.84 (d, 1H,
J = 7.40 Hz, H-8); 13C NMR (100 MHz, CDCl3):
d = 13.90 (–CH2CH2CH3), 21.36 (CH3), 21.80 (–CH2
CH2CH3), 27.70 (C-4), 28.55 (–CH2CH2CH3), 110.02 (C-
50), 121.12 (C-8), 124.61 (C-7), 125.75 (C-200, C-600),
129.05 (C-3a), 129.30 (C-300, C-500), 129.43 (C-6), 131.41
(C-100), 134.92 (C-5), 138.57 (C-400), 138.66 (C-8a), 141.35
(C-4a), 148.69 (C-8b), 153.41 (C-40), 154.28 (C-3), 159.39
(C-20); ESI–MS m/z: 372.2 [M ? 1]?; Anal. Calcd. for
C23H21N3S (371.15): C, 74.36; H, 5.70; N, 11.31. Found:
C, 74.58; H, 5.43; N, 11.57.
4-Phenyl-2-(3-propylindeno[1,2-c]pyrazol-1(4H)-yl)thia-
zole (4e) Offwhite solid; yield 52 %; mp 96–98 °C; IR
(KBr): mmax 731, 1072, 1470, 1510, 1539 (C = N), 2870,
2957 (aliphatic C–H stretch), 3051, 3128 (aromatic C–H
1
stretch) cm-1; H NMR (400 MHz, CDCl3): d = 0.98 (t,
3H, –CH2CH2CH3), 1.72–1.81 (m, 2H, –CH2CH2CH3),
2.71 (t, 2H, –CH2CH2CH3), 3.59 (s, 2H, H-4), 7.24–7.35
123