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Generation and reactivity of 3‐carbethoxy‐5‐phenyl‐ 5H,7H ‐thiazolo[3,4‐ c ]oxazol‐4‐ium‐1‐olate
Author(s) -
Pinho e Melo Teresa M. V. D.,
Gomes Clara S. B.,
Soares Maria I. L.,
Gonsalves Antóanio M. d'A Rocha,
Paixão José A.,
Beja Ana M.,
Silva Manuela Ramos
Publication year - 2004
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.5570410403
Subject(s) - chemistry , dimethyl acetylenedicarboxylate , reactivity (psychology) , thiazole , thiazolidine , medicinal chemistry , thermal decomposition , acetic acid , cycloaddition , stereochemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
3‐Carbethoxy‐5‐phenyl‐5 H ,7 H ‐thiazolo[3,4‐ c ]oxazol‐4‐ium‐1‐olate was generated from (2 R ,4 R )‐ N ‐ethoxyoxalyl‐2‐phenylthiazolidine‐4‐carboxylic acid and its reactivity studied. This münchnone showed low reactivity as dipole although from the reaction with dimethyl acetylenedicarboxylate the corresponding (3 R )‐3‐phenyl‐17 H ,3 H ‐pyrrolo[1,2‐ c ]thiazole‐5,6,7‐tricarboxylate could be isolated. The thermolysis of (2 R ,4 R )‐ N ‐ethoxyoxalyl‐2‐phenylthiazolidine‐4‐carboxylic acid in refluxing acetic anhydride led to the synthesis of N ‐(1‐ethoxycarbonyl‐2‐phenylvinyl)‐2‐phenyl‐4‐thioxo‐1,3‐thiazolidine. The structure of methyl (2 R ,4 R )‐ N ‐ethoxyoxalyl‐2‐phenylthiazoliddine‐4‐carboxylate was determined by X‐ray crystallography.