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Condensation and Cyclization of 2-Hydrazinobenzimidazole, -benzoxazole, and -benzothiazole
Badr, M. Z. A.,Mahmoud, A. M.,Mahgoub, S. A.,Hozien, Z. A.
, p. 1339 - 1344 (2007/10/02)
2-Hydrazinobenzoxazole (1), -benzimidazole (2), and -benzothiazole (3) were condensed with ethyl chloroformate and/or diethyl oxalate to produce 1,2,4-triazolo- and 1,2,4-triazino-fused ketones of the title azoles respectively.Condensation of 1 and 2 with aromatic aldehydes and/or acetic anhydride produced, 3-aryl- and 3-methyl-substituted 1,2,4-triazolo-fused azoles respectively.The hydrazines 1 and 2 cyclized with acetylacetone to produce the corresponding 2-(1-pyrazolyl) derivatives. 2-Acetylthiazolobenzimidazole reacted with hydroxylamine and/or alkylamines, to produce the corresponding condensation products.Also, it condensed with aromatic aldehydes to give the chalcones.When reacted with benzenediazonium salt, it gave the corresponding 2-arylazo-substituted compounds.
