Regiospecificity in the heterocyclization of b-oxonitriles to 5-substituted 4-oxothiazolidine derivatives

Autor: PETER STEEL, MARIJA BARANAC, MILOVAN STOJANOVIC, ZDRAVKO DZAMBASKI, RADE MARKOVIC
Jazyk: angličtina
Rok vydání: 2003
Předmět:
Zdroj: Journal of the Serbian Chemical Society, Vol 68, Iss 4-5, Pp 383-390 (2003)
Druh dokumentu: article
ISSN: 0352-5139
Popis: 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.
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