HETEROCYCLES, Vol. 89, No. 1, 2014
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(s, br, 1H, D2O-exchangable, NH); MS (m/z, %): 588 (M+, 100%); Anal. Calcd for C32H24N6O2S2
(588.70); C, 65.29; H, 4.11; N, 14.28; S, 10.89%. Found: C, 65.25; H, 4.09; N, 14.30; S, 10.85%.
4-(Benzohiazol-2-yl)-5-cyano-1,6-dihydro-6-imino-3-(phenylsulfonyl)-1-(phenyl)pyridazine (31a):
Yield (thermally) 75%; yield (MW) 88%, mp 240−242 °C; IR (KBr) νmax/cm-1: 3332 (NH), 2233 (C≡N),
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1597 (C=N); H NMR (DMSO-d6) δ 6.94−8.14 (m, 14H, ArH’s), 11.78 (br. s, 1H, D2O-exchangable,
NH). MS (m/z, %): 469 (M+, 100%); Anal. Calcd for C24H15N5O2S2 (469.54): C, 61.39; H, 3.22; N, 14.92;
S, 13.66%. Found: C, 61.42; H, 3.24; N, 14.88; S, 13.62%.
4-(Benzothiazol-2-yl)-5-cyano-1,6-dihydro-6-imino-3-(phenylsulfonyl)-1-(4-chlorophenyl)pyridazine
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(31b): Yield (69%), mp > 300 °C; IR (KBr) νmax/cm-1: 3332 (NH), 2233 (C≡N), 1597 (C=N); H NMR
(DMSO-d6) δ 6.64−8.14 (m, 13H, ArH’s), 11.88 (s, br, 1H, D2O-exchangable, NH); 13C NMR
(DMSO-d6) δ 114.88, 123.01, 124.86, 125.41, 126.16, 126.75, 127.54, 128.03, 129.07, 129.46, 129.69,
130.51, 133.33, 133.69, 135.2, 138.48, 140.05, 141.79, 151.06, 156.04; MS (m/z, %): 503 (M+, 100%);
Anal. Calcd for C24H14ClN5O2S2 (503.98): C, 57.20; H, 2.80; N, 13.90; S, 12.72%. Found: C, 57.23; H,
2.82; N, 13.87; S, 12.74%.
4-(Benzothiazol-2-yl)-5-cyano-1,6-dihydro-6-imino-3-(phenylsulfonyl)-1-(4-methylphenyl)pyridazine
(31c): Yield (71%), mp 290−292 °C; IR (KBr) νmax/cm-1: 3352 (NH), 2267 (C≡N), 1593 (C=N); 1H NMR
(DMSO-d6) δ 2.32 (s, 3H, CH3), 6.44−8.14 (m, 13H, ArH’s), 11.88 (s, br, 1H, D2O-exchangable, NH);
13C NMR (DMSO-d6) δ 20.88, 113.37, 123.01, 124.86, 125.45, 126.16, 126.66, 127.41, 127.58, 127.99,
129.53, 129.76, 130.87, 131.51, 133.48, 135.11, 136.07, 137.15, 140.22, 150.9, 156.04; MS (m/z, %): 483
(M+, 100%); Anal. Calcd for C25H17N5O2S2 (483.56): C, 62.09; H, 3.54; N, 14.48; S, 13.26%. Found: C,
62.11; H, 3.51; N, 14.52; S, 13.23%.
4-(1-Methylbenzimidazol-2-yl)-5-cyano-1,6-dihydro-6-imino-3-(phenylsulfonyl)-1-(phenyl)-pyrid-
azine (32a: Yield (thermally) 77%; yield (MW) 89%, mp 220−222 °C; IR (KBr) νmax/cm-1: 3332 (NH),
2233 (C≡N), 1597 (C=N); 1H NMR (DMSO-d6) δ 4.02 (s, 3H, NCH3), 6.54−7.92 (m, 14H, ArH’s), 11.79
(br. s, 1H, D2O-exchangable, NH); MS (m/z, %): 466 (M+, 100%); Anal. Calcd for C25H18N6O2S
(466.51): C, 64.36; H, 3.89; N, 18.01; S, 6.87%. Found: C, 64.41; H, 3.86; N, 18.04; S, 6.89%.
4-(1-Methylbenzimidazol-2-yl)-5-cyano-1,6-dihydro-6-imin-3-(phenylsulfonyl)-1-(4-chlorophenyl)-
pyridazine (32b): Yield (74%), mp >300 °C; IR (KBr) νmax/cm-1: 3352 (NH), 2267 (C≡N), 1593 (C=N);
1H NMR (DMSO-d6) δ 4.05 (s, 3H, CH3), 6.59−7.92 (m, 13H, ArH’s), 11.82 (br. s, 1H, D2O-exchangable,
NH); MS (m/z, %): 500 (M+, 100%); Anal. Calcd for C25H17ClN6O2S (500.96): C, 59.94; H, 3.42; N,
16.78; S, 6.40%. Found: C, 59.90; H, 3.46; N, 16.80; S, 6.36%.
4-(1-Methylbenzimidazol-2-yl)-5-cyano-1,6-dihydro-6-imin-3-(phenylsulfonyl)-1-(4-methylphenyl)-
pyridazine (32c): Yield (78%), mp 242−244 °C; IR (KBr) νmax/cm-1: 3352 (NH), 2267 (C≡N), 1593
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(C=N); H NMR (DMSO-d6) δ 2.32 (s, 3H, CH3), 4.12 (s, 3H, CH3), 6.40−7.92 (m, 13H, ArH’s), 11.81