Synthesis of mesoionic 3-aryl (hetaryl)-1, 2, 3, 4-oxatriazol-5-ones b based on N-aryl-and N-hetarylhydrazones of bromonitroformaldehyde

…, VI Gulevskaya, TI Cherkasova, VM Vinogradov…

Index: Shevelev; Dalinger; Gulevskaya; Cherkasova; Vinogradov; Ugrak; Starosotnikov Chemistry of Heterocyclic Compounds, 1999 , vol. 35, # 3 p. 363 - 373

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Abstract

Abstract Dehydrobromination of N-arylhydrazones of bromonitroformaldehyde (at 20° C) in the presence of alkali and ammonium salts of strong mineral acids, HNO 3, silica gel, and Al 2 O 3 forms mesoionic 3-aryl-1, 2, 3, 4-oxatriazol-5-ones (3-arylazasydnones). The effect of the electronic properties of the aryl substituent on the course of the reaction is evaluated. This evaluation is used to develop a general method for preparing 3-arylazasydnones ...