Synthesis, spectroscopic and structural properties of novel substituted 2-trichloromethyl-3-phenyl-1,3-thiazolidin-4-ones

Roy Issac, John Tierney, Linda M. Mascavage, Alfred Findeisen, James Kilburn

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The reaction of chloral with substituted anilines resulted in formation of the respective 2,2,2-trichloroethylidene anilines. Subsequent treatment of these imines in situ with thioglycolic acid produced a series of substituted 2-trichloromethyl-3-phenyl-1,3-thiazolidin-4-ones, This synthetic route was interesting in light of several other possible intermediates which can be formed on reaction of chloral with amines. High resolution (300 MHz) 1H and 13C magnetic resonance spectra and ab initio calculations gave insight into the conformation of the observed products.

Original languageEnglish (US)
Pages (from-to)227-232
Number of pages6
JournalHeterocyclic Communications
Volume2
Issue number3
DOIs
StatePublished - Jan 1 1996

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Aniline Compounds
Structural properties
Imines
Magnetic resonance
Amines
Conformations
trichloroacetaldehyde

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Issac, Roy ; Tierney, John ; Mascavage, Linda M. ; Findeisen, Alfred ; Kilburn, James. / Synthesis, spectroscopic and structural properties of novel substituted 2-trichloromethyl-3-phenyl-1,3-thiazolidin-4-ones. In: Heterocyclic Communications. 1996 ; Vol. 2, No. 3. pp. 227-232.
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Synthesis, spectroscopic and structural properties of novel substituted 2-trichloromethyl-3-phenyl-1,3-thiazolidin-4-ones. / Issac, Roy; Tierney, John; Mascavage, Linda M.; Findeisen, Alfred; Kilburn, James.

In: Heterocyclic Communications, Vol. 2, No. 3, 01.01.1996, p. 227-232.

Research output: Contribution to journalArticle

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T1 - Synthesis, spectroscopic and structural properties of novel substituted 2-trichloromethyl-3-phenyl-1,3-thiazolidin-4-ones

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AU - Kilburn, James

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AB - The reaction of chloral with substituted anilines resulted in formation of the respective 2,2,2-trichloroethylidene anilines. Subsequent treatment of these imines in situ with thioglycolic acid produced a series of substituted 2-trichloromethyl-3-phenyl-1,3-thiazolidin-4-ones, This synthetic route was interesting in light of several other possible intermediates which can be formed on reaction of chloral with amines. High resolution (300 MHz) 1H and 13C magnetic resonance spectra and ab initio calculations gave insight into the conformation of the observed products.

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