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2004
Thiazole derivatives
R 0260
Generation and Reactivity of 3-Carbethoxy-5-phenyl-5H,7H-thiazolo[3,4-c]ox— N-Ethoxyoxalyl-2-phenylthiazolidine-4-carboxylic acid (IIIa)
51- 099 azol-4-ium-1-olate.
is selectively synthesized from diastereomeric thiazolidinecarboxylic acid (Ia) and used
to generate the title muenchnone (IV). Compound (IV) shows low reactivity as dipole
although pyrrolothiazoletricarboxylate (VI) can be isolated in low yield from the reaction with acetylenedicarboxylate (V). Thermolysis of precursor (IIIa) in refluxing Ac2O
in the absence of any dipolarophile provides an interesting synthesis of N-phenylvinyl-4-thioxothiazolidine (VII) via muenchnone (IV) as intermediate. — (PINHO E
MELO*, T. M. V. D.; GOMES, C. S. B.; SOARES, M. I. L.; ROCHA GONSALVES,
A. M. D.; PAIXAO, J. A.; BEJA, A. M.; RAMOS SILVA, M.; J. Heterocycl. Chem.
41 (2004) 4, 493-497; Dep. Quim., Fac. Cienc. Tecnol., Univ. Coimbra, P-3000
Coimbra, Port.; Eng.) — R. Staver
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