ALKYLATION OF 3-NITRO-1,2,4-TRIAZOLE IN AQUEOUS ALKALINE MEDIUM IN THE PRESENCE OF <i>N</i>-METHYLMORPHOLINE <i>N</i>-OXIDE AND VERIFICATION OF THE STRUCTURE OF THE REACTION PRODUCTS
DOI:
https://doi.org/10.1007/3098Keywords:
allyl bromide, dibromoethane, N-methylmorpholine N-oxide, 3-nitro-1, 2, 4-triazole, propargyl bromide, alkylation, alternative reaction mediumAbstract
It is shown that alkylation of 3-nitro-1,2,4-triazole with alkyl bromides may be carried out in an aqueous alkaline medium in the presence of N-methylmorpholine N-oxide. Alkylation of 3-nitro-1,2,4-triazole with dibromoethane and propargyl bromide occurs regioselectively with the formation of the substitution products at the N-1 atom of the heterocycle. Alkylation with allyl bromide under similar conditions proceeds with low selectivity leading to regioisomeric substitution products at both N-1 and N-2 atoms. Establishing the structures of the obtained regioisomers by NMR spectroscopy and X-ray crystallography is discussed.
Authors: Geghetsik B. Zakaryan, Sargis S. Hayotsyan, Armen G. Ayvazyan, Rafael A. Tamazyan,
Henrik A. Panosyan, Gevorg G. Danagulyan, Hovhannes S. Attaryan*
