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Thiazolidine‐2,4‐dicarboxylic acid and its esters: Synthesis, in solution behaviour and regioselective cyclocondensation
Author(s) -
Refouvelet Bernard,
Robert JeanFranÇOis,
Couquelet Jacques,
Tronche Pierre
Publication year - 1994
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.5570310114
Subject(s) - chemistry , regioselectivity , glyoxylic acid , benzylamine , thiazolidine , organic chemistry , epimer , dicarboxylic acid , hydantoin , bicyclic molecule , medicinal chemistry , acylation , dimethyl acetylenedicarboxylate , catalysis , cycloaddition
Thiazolidine‐2,4‐dicarboxylic acid 2 was obtained as a diastereoisomeric mixture from the condensation of glyoxylic acid with L(‐) R ‐cysteine 1 . In solution behaviour studies suggested that the reaction proceeded through an acid catalyzed epimerization mechanism. The methyl esterification of 2 was stereoselective, which can be explained by an interconversion of 2a via a ring seco intermediate. Condensation of the dimethyl ester 3 or the dissymmetric diester 4 with phenyl isocyanate gave rise to the same hydantoin 5 . N ‐acylation of diesters 3 or 4 followed by the reaction with benzylamine was regioselective leading to bicyclic derivatives 8‐10 .