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

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...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2016-04, Vol.52 (4), p.253-256
Main Authors: Zakaryan, Geghetsik B., Hayotsyan, Sargis S., Ayvazyan, Armen G., Tamazyan, Rafael A., Panosyan, Henrik A., Danagulyan, Gevorg G., Attaryan, Hovhannes S.
Format: Article
Language:English
Subjects:
Bromine compounds
Chemistry
Chemistry and Materials Science
Nuclear magnetic resonance spectroscopy
Organic Chemistry
Pharmacy
Reagents
Triazoles
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Summary: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.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-016-1870-2