A novel rearrangement reaction of 2,5,5-triaryl-2-thiazolin-4-ones during thiation

E. Koltai, J. Nyitrai, K. Lempert, Gy Horváth, A. Kalmán, Gy Argay

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Abstract

2,5,5-Triphenyl-2-thiazolin-4-one (7) is transformed by P2S5 in boiling dioxane or xylene into N-(3-phenyl-2-benzo[b]thienyl)-thiobenzamide (10). The chloro substituted derivatives 16 and 17 of 7 react analogously but, in the case of 17, a by-product which is believed to be the desired 2-thiazoline-4-thione 18 is also formed. The latter may be isomerised subsequently to 20. The structure of 10 was elucidated mainly by mass spectrometry and X-ray. Various chemical transformations of 10 and its chloro substituted derivatives 19 and 20 are discussed.

Original languageEnglish
Pages (from-to)2783-2794
Number of pages12
JournalTetrahedron
Volume29
Issue number18
DOIs
Publication statusPublished - 1973

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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