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

Authors

  • Гегецик Б. Закарян Institute of Organic Chemistry of Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 26 Azatutyan Ave., Yerevan 0014
  • Саркис С. Айоцян Institute of Organic Chemistry of Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 26 Azatutyan Ave., Yerevan 0014
  • Армен Г. Айвазян Molecular Structure Research Center of Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 26 Azatutyan Ave., Yerevan 0014, Armenia
  • Рафаел А. Тамазян Molecular Structure Research Center of Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 26 Azatutyan Ave., Yerevan 0014, Armenia
  • Генрих А. Паносян Molecular Structure Research Center of Scientific and Technological Center of Organic and Pharmaceutical Chemistry of the National Academy of Sciences of the Republic of Armenia, 26 Azatutyan Ave., Yerevan 0014, Armenia
  • Геворг Г. Данагулян Russian–Armenian (Slavonic) University, 123 Hovsep Emin St., Yerevan 0051
  • Оганнес С. Аттарян Российско-Армянский (Славянский) университет, ул. Овсепа Эмина, 123, Ереван 0051

DOI:

https://doi.org/10.1007/3098

Keywords:

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

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*

Author Biography

Оганнес С. Аттарян, Российско-Армянский (Славянский) университет, ул. Овсепа Эмина, 123, Ереван 0051

Russian–Armenian (Slavonic) University,
123 Hovsep Emin St., Yerevan 0051

Published

2016-05-05

Issue

Section

Original Papers