RADICAL-ANIONS IN THE VICARIOUS C-AMINATION REACTIONS OF N-SUBSTITUTED NITROTRIAZOLES

Abstract

The vicarious nucleophilic substitution of hydrogen in symmetrical and vicinal nitrotriazoles by 1,1,1-trimethylhydrazinium iodide in t-BuOK/DMSO was studied by ESR. In the ESR monitoring of the reactions the primary radical-anions of 4-nitro-2-phenyl-1,2,3-triazole and 1-methyl-3-nitro-1,2,4-triazole were detected and characterized. It was shown by NMR that the amination of 4-nitro-2-phenyl-1,2,3-triazole takes place exclusively in the triazole ring with the formation of 5-amino-4-nitro-2-phenyl-1,2,3-triazole. 1-Methyl-3-nitro-1,2,4-triazole, like 3-nitro-1,2,4-triazole, does not form amination products. A possible mechanism for the vicarious C-amination of nitrotriazoles and the formation of the radical-anions of the substrates is discussed. 

How to Cite
Vakul'skaya, T. I.; Titova, I. A.; Larina, L. I.; Verkhozina, O. N.; Dolgushin, G. V.; Lopyrev, V. A.  Chem. Heterocycl. Compd. 2006, 42, 1427. [Khim. Geterotsikl. Soedin. 2006, 1662.]

For this article in the English edition see DOI 10.1007/s10593-006-0259-z