AN UNEXPECTED ROUTE OF ALKYLATION OF 7-SUBSTITUTED (DINITRO)([1,2,4]TRIAZOLO[4,3-<i>a</i>][1,3,5]TRIAZIN-5-YL)METHANIDES WITH ALLYL AND BENZYL BROMIDE

Abstract

Instead of the expected C-alkylation at the dinitromethyl group, the reaction of potassium salts of [7-(dialkylamino)[1,2,4]triazolo[4,3-a][1,3,5]triazin-5-yl](dinitro)methanides with allyl and benzyl bromide led to alkylation at the N-1 and N-2 atoms of the triazole ring to form zwitterionic (dinitro)([1,2,4]triazolo[4,3-a][1,3,5]triazin-1(2)-ium-5-yl)methanides with a positive charge on the nitrogen atom of the 1,2,4-triazole ring, to which an alkyl substituent was attached, and a negative charge localized on the dinitromethyl group. The structure of the products was established on the basis of the NMR spectra and X-ray structural analysis data. The obtained experimental results are in good agreement with the results of quantum-chemical calculations.

Authors: Olga V. Golovina, Andrei K. Shiryaev, Vladimir V. Bakharev*