%0 Journal Article
%T Regiospecificity in the heterocyclization of b-oxonitriles to 5-substituted 4-oxothiazolidine derivatives
%A RADE MARKOVIC
%A ZDRAVKO DZAMBASKI
%A MILOVAN STOJANOVIC
%A PETER STEEL
%J Journal of the Serbian Chemical Society
%D 2003
%I Serbian Chemical Society
%X A study on the regiospecificity of the base-catalyzed reaction of activated b-oxonitriles 1 with diethyl mercaptosuccinate affording the title compounds 3 is reported. Other competitive heterocyclic products, that is 4-oxo-1,3-thiazinanes 4, derivatives of tetrahydrothiophene 5 and/or thiacyclohexane 6 which on the grounds of mechanistic considerations could be formed, were not observed. Spectroscopic and experimental evidence, together with theoretical considerations, provides a reasonable explanation for the observed regiospecificity.
%K regiospecific
%K heterocyclization
%K 4-oxothiazolidines
%U http://www.shd.org.yu/HtDocs/SHD/Vol68/No4-5/V68-No4_5-15.pdf