Abstract
Dehydrobromination of N-arylhydrazones of bromonitroformaldehyde (at 20°C) in the presence of alkali and ammonium salts of strong mineral acids, HNO3, silica gel, and Al2O3 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 with various substituents including novel 3-hetarylazasydnone derivatives of pyrazole, 1,2,4-triazole and pyridine. Aromatic electronic effects (σI, σR, σm, σp) of the mesionic 1,2,3,4-oxatriazol-5-on-3-yl moiety are determined by19F NMR. A scheme is proposed for the dehydrobromination of the bromonitroformaldehyde N-arylhydrazones that includes the intermediate N-aryl-C-(nitro) nitrilimines, ArN−−N=C+NO2, with subsequent isomerization of the latter into 3-arylazasydnones.
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N. D. Zelinskii Institute of Organic Chemistry of the Russian Academy of Sciences, Moscow 117913, Russia
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 413–424, March, 1999.
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Shevelev, S.A., Dalinger, I.L., Gulevskaya, V.I. et al. Synthesis of mesoionic 3-aryl(hetaryl)-1,2,3,4-oxatriazol-5-ones b based on N-aryl-and N-hetarylhydrazones of bromonitroformaldehyde. Chem Heterocycl Compd 35, 363–373 (1999). https://doi.org/10.1007/BF02259369
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DOI: https://doi.org/10.1007/BF02259369