Saturated heterocycle-condensed diphenylisoindolones: Fused-skeleton tetrahydro-1,3-oxazines, oxazolidines and imidazolidines

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

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

The addition of benzene to cis-4-cyclohexene-1,2-dicarboxylic anhydride yielded c-2-benzoyl-t-5-phenyl-r-1-cyclohexanecarboxylic acid (72%), or in another reaction, the 4-phenyl isomer (67%). With bifunctional reagents, saturated tricyclic or partially saturated tetra- and pentacyclic hetero derivatives containing an isoindolone moiety were prepared. The cis → trans isomerization in the ring closures is promoted by enolization and by the two close-lying phenyl groups. The stereostructures of the products were determined via 1H and 13C NMR spectroscopy.

Original languageEnglish
Pages (from-to)187-195
Number of pages9
JournalJournal of Molecular Structure
Volume382
Issue number3
DOIs
Publication statusPublished - Nov 27 1996

Fingerprint

Imidazolidines
Oxazines
Cross-Linking Reagents
Anhydrides
anhydrides
Isomerization
Benzene
musculoskeletal system
Skeleton
Isomers
isomerization
Nuclear magnetic resonance spectroscopy
closures
reagents
Magnetic Resonance Spectroscopy
isomers
benzene
Derivatives
nuclear magnetic resonance
acids

Keywords

  • Configurational isomerism
  • Diphenyl isoindolone
  • NMR spectroscopy

ASJC Scopus subject areas

  • Structural Biology
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Atomic and Molecular Physics, and Optics

Cite this

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title = "Saturated heterocycle-condensed diphenylisoindolones: Fused-skeleton tetrahydro-1,3-oxazines, oxazolidines and imidazolidines",
abstract = "The addition of benzene to cis-4-cyclohexene-1,2-dicarboxylic anhydride yielded c-2-benzoyl-t-5-phenyl-r-1-cyclohexanecarboxylic acid (72{\%}), or in another reaction, the 4-phenyl isomer (67{\%}). With bifunctional reagents, saturated tricyclic or partially saturated tetra- and pentacyclic hetero derivatives containing an isoindolone moiety were prepared. The cis → trans isomerization in the ring closures is promoted by enolization and by the two close-lying phenyl groups. The stereostructures of the products were determined via 1H and 13C NMR spectroscopy.",
keywords = "Configurational isomerism, Diphenyl isoindolone, NMR spectroscopy",
author = "P. Soh{\'a}r and G. St{\'a}jer and Szab{\'o}, {Angela E.} and G. Bern{\'a}th",
year = "1996",
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doi = "10.1016/0022-2860(96)09311-8",
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T1 - Saturated heterocycle-condensed diphenylisoindolones

T2 - Fused-skeleton tetrahydro-1,3-oxazines, oxazolidines and imidazolidines

AU - Sohár, P.

AU - Stájer, G.

AU - Szabó, Angela E.

AU - Bernáth, G.

PY - 1996/11/27

Y1 - 1996/11/27

N2 - The addition of benzene to cis-4-cyclohexene-1,2-dicarboxylic anhydride yielded c-2-benzoyl-t-5-phenyl-r-1-cyclohexanecarboxylic acid (72%), or in another reaction, the 4-phenyl isomer (67%). With bifunctional reagents, saturated tricyclic or partially saturated tetra- and pentacyclic hetero derivatives containing an isoindolone moiety were prepared. The cis → trans isomerization in the ring closures is promoted by enolization and by the two close-lying phenyl groups. The stereostructures of the products were determined via 1H and 13C NMR spectroscopy.

AB - The addition of benzene to cis-4-cyclohexene-1,2-dicarboxylic anhydride yielded c-2-benzoyl-t-5-phenyl-r-1-cyclohexanecarboxylic acid (72%), or in another reaction, the 4-phenyl isomer (67%). With bifunctional reagents, saturated tricyclic or partially saturated tetra- and pentacyclic hetero derivatives containing an isoindolone moiety were prepared. The cis → trans isomerization in the ring closures is promoted by enolization and by the two close-lying phenyl groups. The stereostructures of the products were determined via 1H and 13C NMR spectroscopy.

KW - Configurational isomerism

KW - Diphenyl isoindolone

KW - NMR spectroscopy

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