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

Ferenc Csende, Zoltán Szabó, G. 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
Publication statusPublished - Aug 1 1993

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Hydrochloric Acid
Magnesium
Amines
Methanol
Zinc
Derivatives
Temperature
Acids
Isomers
Condensation
Isoindol-1-one

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis and structural study of new saturated isoindol-1-one derivatives. / Csende, Ferenc; Szabó, Zoltán; Stájer, G.

In: Heterocycles, Vol. 36, No. 8, 01.08.1993, p. 1809-1821.

Research output: Contribution to journalArticle

Csende, Ferenc ; Szabó, Zoltán ; Stájer, G. / Synthesis and structural study of new saturated isoindol-1-one derivatives. In: Heterocycles. 1993 ; Vol. 36, No. 8. pp. 1809-1821.
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