Collect. Czech. Chem. Commun. 1997, 62, 781-790

Reaction of 4-Oxochromene-3-carboxaldehydes with Primary Amides and Benzotriazole or 1H-1,2,4-Triazole

Henrieta Stankovičová, Renata Gašparová, Margita Lácová* and Jarmila Chovancová

Department of Organic Chemistry, Faculty of Natural Science, Comenius University, 842 15 Bratislava, Slovak Republic


N-[(6-substituted-4-oxochromen-3-yl)(1,2,4-triazol-3-yl)methyl]amides 5 and N-[(6-substituted-4-oxochromen-3-yl)(benzotriazol-1-yl)methyl]amides 6 were prepared by the reaction of 6-substituted 4-oxochromene-3-carboxaldehydes 1 with primary amides and 1H-1,2,4-triazole or 1H-benzotriazole. 6-Substituted 3-[hydroxy(1,2,4-triazol-1-yl)methyl]chromen-4-one 2 and 6-substituted 3-[hydroxy(benzotriazol-1-yl)methyl]chromen-4-one 3 were isolated as stable intermediates of these reactions. Beneficial effect of microwave irradiation on length of reaction time was observed. Some reactions of these derivatives with O, S, and N nucleophiles are described.

Keywords: 4-Oxochromene-3-carboxaldehydes; Microwave irradiation; Enamides.