Molecules 2011, 16
619
138.38, 141.44, 148.96, 148.88, 156.78, 157.41, 159.17, 164.45, 168.96; MS: m/z 443 (M+, 26.4%),
446, 445, 444, 443, 317, 260, 190, 188, 150, 144, 127, 111, 90, 75, 51; Anal. Calcd for C23H14ClN5OS:
C, 62.23; H, 3.18; Cl, 7.99; N, 15.78; S: 7.22. Found: C, 62.16; H, 3.12; Cl, 7.90; N, 15.72; S: 7.19%.
5-Naphthalen-1-yl-6-phenylazo-2-thioxo-2,3-dihydro-1H-pyrido[2,3-d]pyramidin-4-one (14b). Orange
1
crystals; m.p. >300 °C; IR: ν 1717 (C=O), 2881, 3055 (2NH) cm-1; H-NMR: δ 7.37-8.12 (m, 12H,
Ar-H), 8.58 (s, 1H, pyridine-H), 12.81 (br., 1H, NH), 13.45 (br., 1H, NH); 13C-NMR: δ 120.67,
122.48, 123.51, 123.78, 124.06, 125.18, 125.58, 128.67, 129.34, 129.89, 131.37, 132.56, 132.83,
134.06, 141.34, 147.89, 154.45, 154.76, 156.87, 165.23, 168.99; MS: m/z 409 (M+, 26.4%), 410, 409,
408, 407, 317, 245, 201, 190, 150, 127, 90, 75, 51; Anal. Calcd for C23H15N5OS: C, 67.47; H, 3.69; N,
17.10; S: 7.83. Found: C, 67.34; H, 3.61; N, 17.04; S: 7.74%.
5-Naphthalen-1-yl-2-thioxo-6-p-tolylazo-2,3-dihydro-1H-pyrido[2,3-d]pyramidin-4-one (14c). Orange
1
crystals; m.p. >300 °C; IR: ν 1717 (C=O), 2881, 3055 (2NH) cm-1; H-NMR: δ 2.26 (s, 3H, CH3),
13
7.11-8.09 (m, 11H, Ar-H), 8.54 (s, 1H, pyridine-H), 12.71 (br., 1H, NH), 13.32 (br., 1H, NH); C-
NMR: δ 19.42, 111.93, 120.93, 122.29, 122.78, 123.24. 124.90, 125.52, 126.26, 127.93, 128.15,
129.51, 131.18, 132.66, 142.06, 143.03, 149.98, 151.74, 159.49, 162.04, 162.61, 175.94; MS: m/z 423
(M+, 17.6%), 424, 423, 317, 245, 201, 190, 150, 127, 90, 75, 51; Anal. Calcd for C24H17N5OS: C,
68.07; H, 4.05; N, 16.54; S: 7.57. Found: C, 67.93; H, 3.95; N, 16.45; S: 7.52%.
3.8. General procedure for preparation of arylpyrazole derivatives 16a,b
Method A: A mixture of the 13a (0.33 g, 1 mmol) and hydrazine derivative (2 mL) in EtOH (10 mL)
was irradiated under constant pressure (11.2 Bar, 80 °C) for 3 min at power of 300 W. The reaction
mixture was cooled and the solid product was collected by filtration and recrystallized from EtOH.
Method B: A mixture of the 13a (3.36 g, 10 mmol) and hydrazine derivative (5 mL) in absolute EtOH
(20 mL) was refluxed for 3 h. The mixture was left to cool and triturated with EtOH. The solid product
was collected by filtration and recrystallized from EtOH.
(4-Chlorophenyl)-(4-naphthalen-1-yl-2H-pyrazol-3-yl)-diazene (16a). Yellow crystals; m.p. 203 °C;
IR: ν 3334 (NH) cm-1; 1H-NMR: δ 7.38-8.32 (m, 11H, Ar-H), 8.45 (s, 1H, pyrazole-H5), 11.92 (br.,1H,
NH); MS: m/z 332 (M+, 11.3%), 335, 334, 333, 332, 324, 311, 296, 155, 127, 107, 91, 77, 51;Anal. Calcd
for C19H13ClN4: C, 68.57; H, 3.94; Cl, 10.65; N, 16.84. Found: C, 68.50; H, 3.89; Cl, 10.61; N, 16.79%.
(4-Chlorophenyl)-(3-naphthalen-1-yl-1-phenyl-1H-pyrazol-4-yl)-diazene (16b). Yellow crystals; m.p.
175 °C; 1H-NMR: δ 7.24-8.12 (m, 16H, Ar-H), 8.36 (s, 1H, pyrazole-H5); 13C-NMR: δ 119.65, 122.56,
124.78, 124.91, 125.67, 126.34, 126.75, 127.09, 127.34, 129.13, 130.08, 132.24, 132.45, 133.12,
136.26, 138.36, 139.66, 140.09, 142.54, 143.68, 154.78; MS: m/z 408 (M+, 11.3%), 410, 409, 408,
380, 331, 297, 268, 241, 163, 127, 111, 107, 91, 77, 51; Anal. Calcd for C25H17ClN4: C, 73.44; H, 4.19;
Cl, 8.67; N, 13.70. Found: C, 73.38; H, 4.14; Cl, 8.61; N, 13.62%.