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Hz, C4–H pyrazoline), 3.99 (s, 2H, NH2), 4.08 (dd, 1H, CH, J ¼ 17H, Ar-H); ESI-MS (m/z): ¼ 776.0 (M + 1); 776.9 (M + 2); anal.
12.0 Hz, 18.0 Hz, C4–H pyrazoline), 4.97 (s, 1H, C4–H, pyran), calcd (%) for C39H26ClF3N10OS: C, 60.43; H, 3.38; N, 18.07;
5.97 (dd, 1H, CH, J ¼ 5.2 Hz, 11.8 Hz, C5–H pyrazoline), 7.33– found: C, 60.34; H, 3.17; N, 17.81.
7.92 (m, 13H, Ar-H), 8.67 (1H, triazole), 8.98 (1H, triazole); ESI-
4.1.4.6. 5-Amino-2-(3-(4-chlorophenyl)-5-(3-(triuoromethyl)
MS (m/z): ¼ 726.1 (M + 1); 727.9 (M + 2); anal. calcd (%) for phenyl)-4,5-dihydro-1H-pyrazol-1-yl)-7-(3-methyl-1-phenyl-5-(1H-
C
35H24ClF3N10OS: C, 57.97; H, 3.34; N, 19.32; found: C, 58.26; H, 1,2,4-triazol-1-yl)-1H-pyrazol-4-yl)-7H-pyrano[2,3-d]thiazole-6-
3.59; N, 19.10.
carbonitrile (11f). Yield 88%; m.p. 256–258 ꢀC; IR (KBr, nmax
,
4.1.4.2. 5-Amino-2-(3-(4-chlorophenyl)-5-(4-(triuoromethyl)- cmꢁ1): 3392 & 3324 (asym. & sym. str. of –NH2), 2187 (C^N str.),
1
phenyl)-4,5-dihydro-1H-pyrazol-1-yl)-7-(3-methyl-5-(4-methyl-1H- 1382 (–CH3 str.), 1238 (C–O–C ether str.); H NMR (400 MHz,
imidazol-1-yl)-1-phenyl-1H-pyrazol-4-yl)-7H-pyrano[2,3-d]thiazole- DMSO-d6): d 2.29 (s, 3H, CH3), 3.52 (dd, 1H, CH, J ¼ 4.4 Hz, 18.4
ꢀ
6-carbonitrile (11b). Yield 76%; m.p. 264–266 C; IR (KBr, nmax
,
Hz, C4–H pyrazoline), 3.97 (s, 2H, NH2), 4.14 (dd, 1H, CH, J ¼
cmꢁ1): 3477 & 3370 (asym. & sym. str. of –NH2), 2202 (C^N 11.6 Hz, 18.4 Hz, C4–H pyrazoline), 4.99 (s, 1H, C4–H, pyran),
str.), 1382 (–CH3 str.), 1218 (C–O–C ether str.); 1H NMR (400 5.95 (dd, 1H, CH, J ¼ 4.4 Hz, 11.2 Hz, C5–H pyrazoline), 7.50–
MHz, DMSO-d6): d 2.15 (s, 3H, CH3), 2.43 (s, 3H, CH3), 3.52 (dd, 7.87 (m, 13H, Ar-H), 8.65 (1H, triazole), 9.04 (1H, triazole); ESI-
1H, CH, J ¼ 4.4 Hz, 18.4 Hz, C4–H pyrazoline), 4.02 (s, 2H, MS (m/z): ¼ 726.0 (M + 1); 727.9 (M + 2); anal. calcd (%) for
NH2), 4.14 (dd, 1H, CH, J ¼ 11.6 Hz, 18.4 Hz, C4–H pyrazoline),
4.91 (s, 1H, C4–H, pyran), 5.95 (dd, 1H, CH, J ¼ 4.0 Hz, 11.2 Hz, 3.50; N, 19.16.
C5–H pyrazoline), 7.19–7.90 (m, 15H, Ar-H); ESI-MS (m/z): ¼ 4.1.4.7. 5-Amino-2-(3-(4-chlorophenyl)-5-(3-(triuoromethyl)-
739.9 (M 1); 741.9 (M 2); anal. calcd (%) for phenyl)-4,5-dihydro-1H-pyrazol-1-yl)-7-(3-methyl-5-(4-methyl-1H-
37H27ClF3N9OS: C, 60.20; H, 3.69; N, 17.08; found: C, 60.21; imidazol-1-yl)-1-phenyl-1H-pyrazol-4-yl)-7H-pyrano[2,3-d]thiazole-
C35H24ClF3N10OS: C, 57.97; H, 3.34; N, 19.32; found: C, 58.20; H,
+
+
C
ꢀ
H, 3.81; N, 16.76.
6-carbonitrile (11g). Yield 75%; m.p. 268–270 C; IR (KBr, nmax,
4.1.4.3. 7-(5-(1H-Imidazol-1-yl)-3-methyl-1-phenyl-1H-pyrazol- cmꢁ1): 3385 & 3331 (asym. & sym. str. of –NH2), 2219 (C^N
4-yl)-5-amino-2-(3-(4-chlorophenyl)-5-(4-(triuoromethyl)phenyl)- str.), 1382 (–CH3 str.), 1215 (C–O–C ether str.); 1H NMR (400
4,5-dihydro-1H-pyrazol-1-yl)-7H-pyrano[2,3-d]thiazole-6-carbonitrile MHz, DMSO-d6): d 2.07 (s, 3H, CH3), 2.41 (s, 3H, CH3), 3.52 (dd,
(11c). Yield 81%; m.p. 256–258 ꢀC; IR (KBr, nmax, cmꢁ1): 3470 & 1H, CH, J ¼ 4.8 Hz, 18.4 Hz, C4–H pyrazoline), 4.01 (s, 2H,
3363 (asym. & sym. str. of –NH2), 2224 (C^N str.), 1381 (–CH3 NH2), 4.14 (dd, 1H, CH, J ¼ 11.6 Hz, 18.4 Hz, C4–H pyrazoline),
1
str.), 1240 (C–O–C ether str.); H NMR (400 MHz, DMSO-d6): d 5.02 (s, 1H, C4–H, pyran), 6.05 (dd, 1H, CH, J ¼ 2.8 Hz, 11.2 Hz,
2.32 (s, 3H, CH3), 3.35 (dd, 1H, CH, J ¼ 6.8 Hz, 15.2 Hz, C4–H C5–H pyrazoline), 7.42–8.16 (m, 15H, Ar-H); ESI-MS (m/z): ¼
pyrazoline), 3.99 (s, 2H, NH2), 4.18 (dd, 1H, CH, J ¼ 7.2 Hz, 15.2 739.8 (M
+ 1); 741.9 (M + 2); anal. calcd (%) for
C37H27ClF3N9OS: C, 60.20; H, 3.69; N, 17.08; found: C, 60.30;
Hz, C4–H pyrazoline), 5.00 (s, 1H, C4–H, pyran), 5.95 (dd, 1H,
CH, J ¼ 11.2 Hz, 16.4 Hz, C5–H pyrazoline), 7.33–7.84 (m, 16H, H, 3.96; N, 16.82.
Ar-H); ESI-MS (m/z): ¼ 725.2 (M + 1); 726.8 (M + 2); anal. calcd
4.1.4.8. 7-(5-(1H-Imidazol-1-yl)-3-methyl-1-phenyl-1H-pyrazol-
(%) for C36H25ClF3N9OS: C, 59.71; H, 3.48; N, 17.41; found: C, 4-yl)-5-amino-2-(3-(4-chlorophenyl)-5-(3-(triuoromethyl)phenyl)-
59.92; H, 3.46; N, 17.26.
4,5-dihydro-1H-pyrazol-1-yl)-7H-pyrano[2,3-d]thiazole-6-carbonitrile
4.1.4.4. 7-(5-(1H-Benzo[d]imidazol-1-yl)-3-methyl-1-phenyl- (11h). Yield 79%; m.p. 250–252 ꢀC; IR (KBr, nmax, cmꢁ1): 3395 &
1H-pyrazol-4-yl)-5-amino-2-(3-(4-chlorophenyl)-5-(4-(triuoro methyl)- 3356 (asym. & sym. str. of –NH2), 2233 (C^N str.), 1371 (–CH3
1
phenyl)-4,5-dihydro-1H-pyrazol-1-yl)-7H-pyrano[2,3-d]thiazole-6- str.), 1210 (C–O–C ether str.); H NMR (400 MHz, DMSO-d6): d
carbonitrile (11d). Yield 71%; m.p. 289–291 ꢀC; IR (KBr, nmax
,
2.33 (s, 3H, CH3), 3.52 (dd, 1H, CH, J ¼ 4.4 Hz, 18.4 Hz, C4–H
cmꢁ1): 3480 & 3369 (asym. & sym. str. of –NH2), 2191 (C^N str.), pyrazoline), 3.97 (s, 2H, NH2), 4.14 (dd, 1H, CH, J ¼ 11.6 Hz, 18.4
1
1369 (–CH3 str.), 1214 (C–O–C ether str.); H NMR (400 MHz, Hz, C4–H pyrazoline), 4.98 (s, 1H, C4–H, pyran), 5.95 (dd, 1H,
DMSO-d6): d 2.26 (s, 3H, CH3), 3.43 (dd, 1H, CH, J ¼ 4.0 Hz, 11.2 CH, J ¼ 5.2 Hz, 11.2 Hz, C5–H pyrazoline), 7.50–7.90 (m, 16H, Ar-
Hz, C4–H pyrazoline), 3.96 (s, 2H, NH2), 4.06 (dd, 1H, CH, J ¼ H); ESI-MS (m/z): ¼ 725.0 (M + 1); 726.9 (M + 2); anal. calcd (%)
11.6 Hz, 17.2 Hz, C4–H pyrazoline), 4.99 (s, 1H, C4–H, pyran), for C36H25ClF3N9OS: C, 59.71; H, 3.48; N, 17.41; found: C, 59.96;
5.99 (dd, 1H, CH, J ¼ 8.4 Hz, 18.0 Hz, C5–H pyrazoline), 7.23– H, 3.42; N, 17.53.
7.98 (m, 18H, Ar-H); ESI-MS (m/z): ¼ 774.5 (M + 1); 776.4 (M + 2);
4.1.4.9. 7-(5-(1H-benzo[d]imidazol-1-yl)-3-methyl-1-phenyl-
anal. calcd (%) for C40H27ClF3N9OS: C, 62.05; H, 3.52; N, 16.28; 1H-pyrazol-4-yl)-5-amino-2-(3-(4-chlorophenyl)-5-(3-(triuoro methyl)-
found: C, 61.84; H, 3.62; N, 16.13. phenyl)-4,5-dihydro-1H-pyrazol-1-yl)-7H-pyrano[2,3-d]thiazole-6-
4.1.4.5. 7-(5-(1H-Benzo[d][1,2,3]triazol-1-yl)-3-methyl-1-phenyl- carbonitrile (11i). Yield 73%; m.p. 277–279 ꢀC; IR (KBr, nmax
,
1H-pyrazol-4-yl)-5-amino-2-(3-(4-chlorophenyl)-5-(4-(triuoro methyl)- cmꢁ1): 3486 & 3373 (asym. & sym. str. of –NH2), 2199 (C^N str.),
1
phenyl)-4,5-dihydro-1H-pyrazol-1-yl)-7H-pyrano[2,3-d]thiazole-6- 1373 (–CH3 str.), 1233 (C–O–C ether str.); H NMR (400 MHz,
carbonitrile (11e). Yield 72%; m.p. 282–284 ꢀC; IR (KBr, nmax
,
DMSO-d6): d 2.24 (s, 3H, CH3), 3.42 (dd, 1H, CH, J ¼ 4.0 Hz, 18.0
cmꢁ1): 3390 & 3339 (asym. & sym. str. of –NH2), 2199 (C^N str.), Hz, C4–H pyrazoline), 3.99 (s, 2H, NH2), 4.11 (dd, 1H, CH, J ¼
1
1369 (–CH3 str.), 1235 (C–O–C ether str.); H NMR (400 MHz, 11.6 Hz, 18.0 Hz, C4–H pyrazoline), 4.98 (s, 1H, C4–H, pyran),
DMSO-d6): d 2.46 (s, 3H, CH3), 3.53 (dd, 1H, CH, J ¼ 4.4 Hz, 18.4 6.01 (dd, 1H, CH, J ¼ 8.4 Hz, 17.6 Hz, C5–H pyrazoline), 7.33–
Hz, C4–H pyrazoline), 4.07 (s, 2H, NH2), 4.11 (dd, 1H, CH, J ¼ 7.2 7.83 (m, 18H, Ar-H); ESI-MS (m/z): ¼ 774.7 (M + 1); 776.6 (M + 2);
Hz, 15.2 Hz, C4–H pyrazoline), 4.95 (s, 1H, C4–H, pyran), 5.95 anal. calcd (%) for C40H27ClF3N9OS: C, 62.05; H, 3.52; N, 16.28;
(dd, 1H, CH, J ¼ 4.4 Hz, 11.2 Hz, C5–H pyrazoline), 7.18–7.84 (m, found: C, 61.76; H, 3.60; N, 16.20.
32360 | RSC Adv., 2014, 4, 32353–32362
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