REACTIONS OF 1,3,5-TRIAZINYLNITROFORMALDOXIME. 4. SYNTHESIS OF (5-R-1,2,4-OXADIAZOL-3-YL)-1,3,5-TRIAZINES

Authors

  • В. В. Бахарев Samara State Technical University
  • А. А. Гидаспов Samara State Technical University
  • Е. В. Селезнева Samara State Technical University
  • В. Е. Парфенов Samara State Technical University
  • И. В. Ульянкина Samara State Technical University
  • И. С. Назарова Samara State Technical University
  • Ю. Т. Палатова Samara State Technical University
  • О. С. Ельцов Ural Federal University named after the First President of Russia B. N. Yeltsin

DOI:

https://doi.org/10.1007/1371

Keywords:

(5-R-1, 2, 4-oxadiazol-3-yl)-1, 3, 5-triazines, 1, 5-triazinylamidoximes, 5-triazinylnitrile oxides, 5-triazinylnitroformaldoximes, acylation, intramolecular cyclization

Abstract

Heating 4-R-methoxy-1,3,5-triazin-2-ylnitroformaldoximes with nitriles leads not to the formation of 1,2,4-oxadiazoles but rather to dimerization of the intermediate 1,3,5-triazinylnitrile oxides to give furoxanes. The reaction of 4-R-6-methoxy-1,3,5-triazin-2-ylnitroformaldoximes with ammonia and amines gives 1,3,5-triazinylamidoximes, which upon acylation and subsequent intramolecular cyclization yield (5-R-1,2,4-oxadiazol-3-yl)-1,3,5-triazines.

Authors: V. V. Bakharev, A. A. Gidaspov, E. V. Selezneva, V. E. Parfenov, I. V. Ul'yankina, I. S. Nazarova, Yu. T. Palatova, and O. S. El'tsov.

English translation in Chemistry of Heterocyclic Compounds, 2011, 47 (10), pp 1258-1267

http://link.springer.com/article/10.1007/s10593-012-0901-x

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Published

2013-12-13

Issue

No. 10 (2011)

Section

Original Papers