REACTIONS OF 2-ARYLHYDRAZONOACETAMIDES WITH ORTHOESTERS. SYNTHESIS OF NEW TETRAHYDRO-1,2,4-TRIAZINES

Authors

  • Н. П. Бельская Urals State Technical University, Ekaterinburg
  • Е. Е. Зверева Urals State Technical University, Ekaterinburg
  • Л. А. Бабушкина Urals State Technical University, Ekaterinburg
  • В. А. Бакулев Urals State Technical University, Ekaterinburg

DOI:

https://doi.org/10.1007/316

Keywords:

arylhydrazones, orthoesters, tetrahydrotriazinones

Abstract

The reactions of arylhydrazonocyanoacetamides with triethyl orthoformate and triethyl orthoacetate have been studied. Interaction of triethyl orthoformate with amides bearing normal alkyl substituents on the carbamoyl group resulted in cyclization to 2-aryl-4-alkyl-5-oxo-3-ethoxy-2,3,4,5-tetrahydro-1,2,4-triazin-6-carbonitriles, whereas reaction of N-phenyl- and N-cycloalkylacetamides with triethyl orthoformate gave products of ethylation at the hydrazone group. Reactions of arylhydrazonocyanoacetamides with triethyl orthoacetate led to 2-(arylethylhydrazono)acetamides exclusively.

Authors: N. P. Bel'skaya, E. E. Zvereva, L. A. Babushkina, and V. A. Bakulev.

English Translation in Chemistry of Heterocyclic Compounds, 2000, 36 (9), pp 1066-1076

http://link.springer.com/article/10.1023/A%3A1002738100046

Published

2013-02-14

Issue

Section

Original Papers