The formation of 2,3‐disubstituted thiazolidin‐4‐ones from s‐α'‐aminomercaptoacetic acid derivatives

John Tierney

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

Variously substituted N‐benzylidineanilines rapidly react with thioglycolic acid to generate S‐α'‐aminomercaptoacetic acid derivatives. The latter subsequently cyclize to the corresponding 2,3‐diarylthiazolidin‐4‐ones. Kinetics for the first order cyclization reaction in the solvents toluene, carbon tetrachloride and nitrobenzene have been obtained over the temperature range 333 K to 383 K and are in accord with a neutral, but geometrically complex transition state.

Original languageEnglish (US)
Pages (from-to)997-1001
Number of pages5
JournalJournal of Heterocyclic Chemistry
Volume26
Issue number4
DOIs
StatePublished - Jan 1 1989

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Carbon Tetrachloride
Cyclization
Toluene
Derivatives
Kinetics
Acids
Temperature
2-mercaptoacetate
nitrobenzene

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

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abstract = "Variously substituted N‐benzylidineanilines rapidly react with thioglycolic acid to generate S‐α'‐aminomercaptoacetic acid derivatives. The latter subsequently cyclize to the corresponding 2,3‐diarylthiazolidin‐4‐ones. Kinetics for the first order cyclization reaction in the solvents toluene, carbon tetrachloride and nitrobenzene have been obtained over the temperature range 333 K to 383 K and are in accord with a neutral, but geometrically complex transition state.",
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The formation of 2,3‐disubstituted thiazolidin‐4‐ones from s‐α'‐aminomercaptoacetic acid derivatives. / Tierney, John.

In: Journal of Heterocyclic Chemistry, Vol. 26, No. 4, 01.01.1989, p. 997-1001.

Research output: Contribution to journalArticle

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N2 - Variously substituted N‐benzylidineanilines rapidly react with thioglycolic acid to generate S‐α'‐aminomercaptoacetic acid derivatives. The latter subsequently cyclize to the corresponding 2,3‐diarylthiazolidin‐4‐ones. Kinetics for the first order cyclization reaction in the solvents toluene, carbon tetrachloride and nitrobenzene have been obtained over the temperature range 333 K to 383 K and are in accord with a neutral, but geometrically complex transition state.

AB - Variously substituted N‐benzylidineanilines rapidly react with thioglycolic acid to generate S‐α'‐aminomercaptoacetic acid derivatives. The latter subsequently cyclize to the corresponding 2,3‐diarylthiazolidin‐4‐ones. Kinetics for the first order cyclization reaction in the solvents toluene, carbon tetrachloride and nitrobenzene have been obtained over the temperature range 333 K to 383 K and are in accord with a neutral, but geometrically complex transition state.

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