REACTION OF 2-ARYLHYDRAZONO-2-CYANO-N-CYCLOHEXYLTHIOACETAMIDES WITH HALOCARBONYL COMPOUNDS

Authors

  • Т. Г. Дерябина Urals State Technical University, Ekaterinburg
  • Н. П. Бельская Urals State Technical University, Ekaterinburg
  • М. И. Кодесс Institute of Organic Synthesis, Urals Branch of the Russian Academy of Sciences, Ekaterinburg
  • В. А. Бакулев Urals State Technical University, Ekaterinburg

DOI:

https://doi.org/10.1007/7696

Keywords:

arylhydrazonothioacetamides, halocarbonyl compounds, thiazoles, thioamide group, thioimidates, thiophenes, alkylation, cyclization

Abstract

The reaction of arylhydrazonocyanothioacetamides containing an N-cyclohexyl fragment with chloroacetone, phenacyl bromide, ethyl chloroacetate, and chloroacetonitrile was investigated. It was shown that a substituent with a large steric effect in the thioamide group alters the direction of intramolecular cyclization of the thioimidate intermediate. In contrast to the Hantsch reaction, which usually leads to the formation of thiazoles  under these conditions, the only products are 3-amino-4-arylhydrazono-4,5-dihydrothiophenes. 

How to Cite
Deryabina, T. G.; Bel'skaya, N. P.; Kodess, M. I.; Bakulev, V. A.  Chem. Heterocycl. Compd. 2007, 43, 18. [Khim. Geterotsikl. Soedin. 2007, 22.]

For this article in the English edition see DOI 10.1007/s10593-007-0003-3


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Published

2023-04-05

Issue

No. 1 (2007)

Section

Original Papers