Synthesis and steric structure determination of 9b-p-tolyl-perhydrothiazolo[2,3-a]isoindolone isomers

Géza Stájer, Angela E. Szabó, Ferenc Csende, Gábor Bernáth, Pál Sohár

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6 Citations (Scopus)

Abstract

The reaction of cis-2-(p-methylbenzoyl)-1-cyclohexanecarboxylic acid (1) and 2-aminoethanethiol furnished three 9b-p-tolylperhydrothiazolo[2,3-a]isoindolone isomers (2-4). The steric structures of the saturated cis (3, 4) and trans (2) isoindolones were determined by 1H and 13C NMR spectroscopy, including DNOE, DEPT and HSC measurements. In the two cis isomers, the steric positions of the tolyl group are different. The cis → trans isomerization can be rationalized by enolization of the starting oxoacid 1.

Original languageEnglish
Pages (from-to)101-104
Number of pages4
JournalJournal of Molecular Structure
Volume377
Issue number2
Publication statusPublished - Jan 1 1996

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Keywords

  • Cis → transisomerization
  • NMR spectroscopy
  • Saturated heterocycles
  • Synthesis

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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