Regiospecificty in the heterocyclization of β-oxonitriles to 5-substituted 4-oxothiazolidine derivatives | Zendy

Rade Marković | Zendy; Zdravko Džambaski | Zendy; Milovan Stojanović | Zendy; Peter J. Steel | Zendy; Marija BaranacStojanović | Zendy

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Regiospecificty in the heterocyclization of β-oxonitriles to 5-substituted 4-oxothiazolidine derivatives

Author(s) -

Rade Marković,

Zdravko Džambaski,

Milovan Stojanović,

Peter J. Steel,

Marija BaranacStojanović

Publication year - 2003

Publication title -

journal of the serbian chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.227

H-Index - 45

eISSN - 1820-7421

pISSN - 0352-5139

DOI - 10.2298/jsc0305383m

Subject(s) - tetrahydrothiophene , chemistry , base (topology) , catalysis , combinatorial chemistry , computational chemistry , medicinal chemistry , organic chemistry , mathematics , mathematical analysis

A study on the regiospecificity of the base-catalyzed reaction of activated -oxo- nitriles 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 tetra- hydrothiophene 5 and/or thiacyclohexane 6 which on the grounds of mechanistic consider- ations could be formed, were not observed. Spectroscopic and experimental evidence, to- gether with theoretical considerations, provides a reasonable explanation for the observed regiospecificity.

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