Pyrazolines 1a-c were prepared according to Rezessy et al. [3] and pyrazoline 1d was prepared
according to Kaplancikli et al. [4].
Acetamides 2a-d (General Method). A mixture of (1 mmol) 1-aminothiocarbonyl-3,5-diaryl-
4,5-dihydro-1H-pyrazole 1 and N-arylmaleimide (1 mmol) in acetic acid (0.8 ml) was heated at reflux for
10 min. The reaction mixture was cooled and diluted with acetone (10 ml). The precipitate of acetamide 2 was
filtered off, washed with acetone, and dried in the air.
N-Phenyl-2-[2-(3,5-diphenyl-4,5-dihydro-1H-pyrazol-1-yl)-4-oxo-4,5-dihydro-1,3-thiazol-5-yl]acet-
amide (2a) was obtained in 75% yield; mp 259-260°C (acetone). IR spectrum, ν, cm-1: 1532, 1602, 1681, 3318.
1H NMR spectrum, δ, ppm (J, Hz): 2.65 (1H, dd, 3J = 11.3, 2J = 16.5, Ha); 3.21 (1H, dd, 3J = 3.7, 2J = 16.5, Hb);
3
2
3
2
3
3
3.38 (1H, dd, J = 4.0, J = 18.3, Hd); 4.11 (1H, dd, J = 11.3, J = 18.3, He); 4.39 (1H, dd, J = 3.7, J = 11.3,
Hc); 5.80 (1H, dd, 3J = 4.0, 3J = 11.3, Hf); 7.0-7.9 (15H, m, ArH); 10.1 (1H, s, NH). 13C NMR spectrum, δ, ppm:
40.0, 43.2, 50.1, 63.4, 119.1, 123.1, 125.3, 127.0, 127.5, 128.3, 128.5, 128.6, 129.6, 131.1, 138.5, 140.1, 160.3,
168.2, 176.8, 187.5. Found, %: N 12.40. C26H22N4O2S. Calculated, %: N 12.33.
N-(3-Chloro-4-fluorophenyl)-2-[2-(3-(4-methoxyphenyl)-5-p-tolyl-4,5-dihydro-1H-pyrazol-1-yl)-
4-oxo-4,5-dihydro-1,3-thiazol-5-yl]acetamide (2b) was obtained in 72% yield, mp 247-248°C (acetone). IR
1
spectrum, ν, cm-1: 1510, 1541, 1608, 1677, 3307. H NMR spectrum, δ, ppm (J, Hz): 2.28 (3H, s, CH3); 2.72
3
2
3
2
3
2
(1H, dd, J = 11.0, J = 16.4, Ha); 3.21 (1H, dd, J = 3.5, J = 6.4, Hb); 3.28 (1H, dd, J = 4.0, J = 18.0, Hd);
3.83 (3H, s, CH3O); 4.06 (1H, dd, 3J = 11.1, 2J = 18.0, He); 4.37 (1H, dd, 3J = 3.5, 3J = 11.0, Hc); 5.74 (1H, dd,
3
3J = 4.0, J = 11.1, Hf); 7.0-8.0 (12H, m, ArH); 10.36 (1H, s, NH). Mass spectrum, m/z (Irel, %): 550 [M]+ (2),
378 (14), 224 (19), 145 (23), 117 (64), 55 (100). Found, %: N 10.22. C28H24ClFN4O3S. Calculated, %: N 10.17.
N-(4-Fluorophenyl-2-[2-(5-(3-chlorophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-
4-oxo-4,5-dihydro-1,3-thiazol-5-yl]acetamide (2c) was obtained in 68% yield; mp 278-279° (acetone). IR
1
spectrum, ν, cm-1: 1508, 1533, 1674, 1693, 3273, 3297. H NMR spectrum, δ, ppm (J, Hz): 2.72 (1H, dd,
2
3
2
3
2
3J = 11.1, J = 16.4, Ha); 3.15 (1H, dd, J = 3.6, J = 16.4, Hb); 3.5 (1H, dd, J = 4.0, J = 18.0, Hd); 4.10 (1H,
3
2
3
3
3
3
dd, J = 11.1, J = 18.0, He); 4.4 (1H, dd, J = 3.6, J = 11.1, Hc); 5.8 (1H, dd, J = 4.0, J = 11.1, Hf); 7.0-8.0
(12H, m, ArH); 10.15 (1H, s, NH). Mass spectrum, m/z (Irel, %): 524 [M]+ (16), 386 (100), 258 (20), 211 (16),
162 (26), 137 (24), 121 (24), 110 (38). Found, %: N 10.78. C26H19ClF2N4O2S. Calculated, %: N 10.67.
N-(3-Methoxyphenyl)-2-[2-(5-phenyl-3-(2-thienyl)-4,5-dihydro-1H-pyrazol-1-yl)-4-oxo-4,5-dihydro-
1,3-thiazol-5-yl]acetamide (2d) was obtained in 70% yield; mp 273-274°C (acetone). IR spectrum, ν, cm-1:
1
3
2
1533, 1615, 1679, 1703, 3319. H NMR spectrum, δ, ppm (J, Hz): 2.70 (1H, dd, J = 11.3, J = 16.4, Ha); 3.21
3
2
3
2
(1H, dd, J = 3.5, J = 16.4, Hb); 3.40 (1H, dd, J = 3.9, J = 18.0, Hd); 3.80 (3H, s, CH3O); 4.12 (1H, dd,
3J = 11.1, J = 18.0, He); 4.38 (1H, dd, J = 3.5, J = 11.3, Hc); 5.78 (1H, dd, J = 3.9, J = 11.1, Hf); 6.6-7.9
(13H, m, ArH); 10.1 (1H, s, NH). Mass spectrum, m/z (Irel, %): 490 [M]+ (10), 340 (74), 227 (17), 203 (17), 176
(27), 149 (44), 103 (100). Found, %: N 11.47. C25H22N4O3S2. Calculated, %: N 11.42.
3
3
3
3
3
REFERENCES
1.
2.
T. Takido and K. Itabashi, Synthesis, 430 (1985).
T. Takido, S. Tamura, K. Sato, H. Kamijo, T. Nakazawa, T. Hata, and M. Seno, J. Heterocycl. Chem.,
35, 437 (1998).
3.
4.
B. Rezessy, Z. Zubovics, J. Kovács Jozsef, and G. Toth, Tetrahedron, 55, 5909 (1999).
Z. A. Kaplancikli, G. Turan-Zitouni, A. Ozdemir, G. Revial, and K. Gueven, Phosphorus, Sulfur,
Silicon, Relat. Elem., 182, 749 (2007).
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