Synthesis and Heterocyclization of 3-Arylaminothiocrotonanilides
Authors: Borisevich, A.N.; Samoilenko, L.S.; Lozinskii, M.O.; Rusanov, E.B.; Chernega, A.N.
Source: Russian Journal of General Chemistry, Volume 71, Number 11, November 2001 , pp. 1767-1770(4)
Publisher: MAIK Nauka/Interperiodica
Abstract:Reactions of acetylthioacetanilide with arylamines in acetic acid in the presence of sodium acetate give 3-arylaminothiocrotonanilides in good yields. When treated with -bromoacetophenone in acetone, these products are converted to substituted 4-hydroxy-Δ^2-thiazolinium bromides, one of which was dehydrated to obtain the corresponding thiazolium bromide. The structure of the heterocyclization products was confirmed by single crystal X-ray diffraction and NMR study of 2-acetonylidene-3,4-diphenyl-2,3-dihydrothiazole formed by dehydration of the corresponding Δ^2-thiazolinium salt with simultaneous hydrolysis.
Document Type: Regular Paper
Affiliations: Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev, Ukraine
Publication date: 2001-11-01