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Synthesis and in solution behaviour of new 2‐substituted‐4‐thiazolidinecarboxylic acid derivatives
Author(s) -
Chiarino D.,
Ferrario F.,
Pellacini F.,
Sala A.
Publication year - 1989
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570260313
Subject(s) - diastereomer , chemistry , thiazolidine , ring (chemistry) , center (category theory) , stereochemistry , organic chemistry , combinatorial chemistry , crystallography
A number of 2‐substituted‐4‐thiazolidinecarboxylic acid derivatives were synthesized by cyclocondensation of L‐cysteine or its esters with various aldehydes, resulting from acids provided with antiinflammatory properties. In the cyclocondensation a new chiral center at C‐2 position of thiazolidine ring is formed giving rise to a mixture of diastereoisomers which can be partially separated. These diastereoisomers show in solution a fast epimerisation at the same chiral center as evidenced by 1 H‐nmr studies.