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ALKYLATION OF 3-NITRO-1,2,4-TRIAZOLE IN AQUEOUS ALKALINE MEDIUM IN THE PRESENCE OF N-METHYLMORPHOLINE N-OXIDE AND VERIFICATION OF THE STRUCTURE OF THE REACTION PRODUCTS

Гегецик Б. Закарян, Саркис С. Айоцян, Армен Г. Айвазян, Рафаел А. Тамазян, Генрих А. Паносян, Геворг Г. Данагулян, Оганнес С. Аттарян
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Abstract


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*


Keywords


allyl bromide; dibromoethane; N-methylmorpholine N-oxide; 3-nitro-1,2,4-triazole; propargyl bromide; alkylation; alternative reaction medium

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