Preparation and steric structure of condensed-skeleton saturated diphenyl-substituted isoindolones

G. Stájer, Angela E. Szabó, G. Bernáth, P. Sohár

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Abstract

The Friedel-Crafts reaction of benzene with cis-4-cyclohexene1,2-dicarboxylic anhydride (1) yields trans-5-phenyl-cis-2-benzoylcyclohexanecarboxylic acid (2), which gave cyclohexane-condensed pyridazinone (3) with hydrazine, and cis-4,5-tetramethylene-1,2-oxazin-8-one (4) with hydroxylamine. From 2 with ethylenediamine, the saturated imidazo[2,3-α]isoindolone (5) was prepared, while the reaction of 2 with 1,3-diaminopropane furnished a mixture of two isomeric pyrimido[2,3-α]isoindolones (6a,b) differing in the relative positions of the benzene ring and cyclohexane annelation hydrogens. From the reaction of 2 with 3-aminopropanol, the oxazino[2,3-α]isoindolone (7) was obtained. The reaction of 2 with cis2-hydroxymethylcyclohexylamine gave the tetracyclic (8), while 2 and diendo-3-hydroxymethylbicyclo[2.2.1]hept-5-enyl-2-amine yielded the isomers (9a,b), which differ in the mutual positions of the phenyl group on the quaternary carbon and cyclohexane annelation hydrogens. 1H- and 13C-nmr spectra and DNOE and 2D-HSC measurements proved that the 5-phenyl group is cis-equatorial to the two annelated hydrogens of the cyclohexane ring.

Original languageEnglish
Pages (from-to)1061-1070
Number of pages10
JournalHeterocycles
Volume38
Issue number5
Publication statusPublished - May 1 1994

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Skeleton
Hydrogen
ethylenediamine
hydrazine
Benzene
Propanolamines
Friedel-Crafts reaction
Hydroxylamine
Anhydrides
Isomers
Amines
Carbon
Acids
diphenyl
Cyclohexane
Isoindol-1-one

ASJC Scopus subject areas

  • Organic Chemistry

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Preparation and steric structure of condensed-skeleton saturated diphenyl-substituted isoindolones. / Stájer, G.; Szabó, Angela E.; Bernáth, G.; Sohár, P.

In: Heterocycles, Vol. 38, No. 5, 01.05.1994, p. 1061-1070.

Research output: Contribution to journalArticle

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AB - The Friedel-Crafts reaction of benzene with cis-4-cyclohexene1,2-dicarboxylic anhydride (1) yields trans-5-phenyl-cis-2-benzoylcyclohexanecarboxylic acid (2), which gave cyclohexane-condensed pyridazinone (3) with hydrazine, and cis-4,5-tetramethylene-1,2-oxazin-8-one (4) with hydroxylamine. From 2 with ethylenediamine, the saturated imidazo[2,3-α]isoindolone (5) was prepared, while the reaction of 2 with 1,3-diaminopropane furnished a mixture of two isomeric pyrimido[2,3-α]isoindolones (6a,b) differing in the relative positions of the benzene ring and cyclohexane annelation hydrogens. From the reaction of 2 with 3-aminopropanol, the oxazino[2,3-α]isoindolone (7) was obtained. The reaction of 2 with cis2-hydroxymethylcyclohexylamine gave the tetracyclic (8), while 2 and diendo-3-hydroxymethylbicyclo[2.2.1]hept-5-enyl-2-amine yielded the isomers (9a,b), which differ in the mutual positions of the phenyl group on the quaternary carbon and cyclohexane annelation hydrogens. 1H- and 13C-nmr spectra and DNOE and 2D-HSC measurements proved that the 5-phenyl group is cis-equatorial to the two annelated hydrogens of the cyclohexane ring.

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