Synthesis and structural study of new saturated isoindol-1-one derivatives

Ferenc Csende, Zoltán Szabó, Géza Stájer

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Condensation of 2-p-toluoylcyclohexanecarboxylic acid (1a,b) with primary amines gave the corresponding hexahydroisoindol-1-ones (2a-g) in good yield. The octahydro derivatives (4a-g) were prepared from cis- and trans-hexahydro-1(2H)-phthalazinone (3a,b) by reduction with zinc-hydrochloric acid via ring contraction. Stereoselective synthesis of cis-N-phenyloctahydroisoindol-1-one (4h) was performed starting from 2b by reduction with magnesium-methanol at room temperature. Configurational assignments of cis and trans isomers were based on 1H-and 13C-nmr spectroscopic studies.

Original languageEnglish
Pages (from-to)1809-1821
Number of pages13
JournalHeterocycles
Volume36
Issue number8
DOIs
Publication statusPublished - Aug 1 1993

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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