Synthesis and stereostructure of saturated isoindolone-fused hetero tri-, tetra-, and pentacyclic compounds

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Abstract

t-2-Benzoyl-t-4-phenylcyclohexane-r-1-carboxylic acid reacts with hydrazine to give the saturated 1,7-diphenyl-trans-phthalazin-4(3H)-one. The reaction of the acid with ethylenediamine yields diastereomeric trans-imidazo[2,3-a] isoindoles, which differ in their C-1 configuration. The cyclizations of the acid with cis-2-aminocyclohexane- or 4-cyclohexenemethanol result in trans-isoindolo[2,1-a][3,1]benzoxazines, while in its reactions with the analogous di-endo- and di-exo-norbornane- and -norborneneamino alcohols, the acid gives methylene-bridged isomeric di-endo-norbornanes or a norbornene derivative; the corresponding diastereomeric di-exo derivatives have also been prepared. After isolation, the structures were established by means of 1H and 13C NMR spectroscopy, with application of DIFFNOE, DEPT, HMQC, HMBC, and 2D-COSY techniques.

Original languageEnglish
Pages (from-to)1519-1527
Number of pages9
JournalMonatshefte fur Chemie
Volume135
Issue number12
DOIs
Publication statusPublished - dec. 2004

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Norbornanes
ethylenediamine
hydrazine
Acids
Isoindoles
Benzoxazines
Derivatives
Cyclization
Carboxylic Acids
Nuclear magnetic resonance spectroscopy
Alcohols
Isoindol-1-one

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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abstract = "t-2-Benzoyl-t-4-phenylcyclohexane-r-1-carboxylic acid reacts with hydrazine to give the saturated 1,7-diphenyl-trans-phthalazin-4(3H)-one. The reaction of the acid with ethylenediamine yields diastereomeric trans-imidazo[2,3-a] isoindoles, which differ in their C-1 configuration. The cyclizations of the acid with cis-2-aminocyclohexane- or 4-cyclohexenemethanol result in trans-isoindolo[2,1-a][3,1]benzoxazines, while in its reactions with the analogous di-endo- and di-exo-norbornane- and -norborneneamino alcohols, the acid gives methylene-bridged isomeric di-endo-norbornanes or a norbornene derivative; the corresponding diastereomeric di-exo derivatives have also been prepared. After isolation, the structures were established by means of 1H and 13C NMR spectroscopy, with application of DIFFNOE, DEPT, HMQC, HMBC, and 2D-COSY techniques.",
keywords = "Diastereomers, DIFFNOE, Isoindolones, Methanobenzoxazinones, NMR",
author = "P. Soh{\'a}r and A. Cs{\'a}mpai and G. Magyarfalvi and Szab{\'o}, {Angela E.} and G. St{\'a}jer",
year = "2004",
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T1 - Synthesis and stereostructure of saturated isoindolone-fused hetero tri-, tetra-, and pentacyclic compounds

AU - Sohár, P.

AU - Csámpai, A.

AU - Magyarfalvi, G.

AU - Szabó, Angela E.

AU - Stájer, G.

PY - 2004/12

Y1 - 2004/12

N2 - t-2-Benzoyl-t-4-phenylcyclohexane-r-1-carboxylic acid reacts with hydrazine to give the saturated 1,7-diphenyl-trans-phthalazin-4(3H)-one. The reaction of the acid with ethylenediamine yields diastereomeric trans-imidazo[2,3-a] isoindoles, which differ in their C-1 configuration. The cyclizations of the acid with cis-2-aminocyclohexane- or 4-cyclohexenemethanol result in trans-isoindolo[2,1-a][3,1]benzoxazines, while in its reactions with the analogous di-endo- and di-exo-norbornane- and -norborneneamino alcohols, the acid gives methylene-bridged isomeric di-endo-norbornanes or a norbornene derivative; the corresponding diastereomeric di-exo derivatives have also been prepared. After isolation, the structures were established by means of 1H and 13C NMR spectroscopy, with application of DIFFNOE, DEPT, HMQC, HMBC, and 2D-COSY techniques.

AB - t-2-Benzoyl-t-4-phenylcyclohexane-r-1-carboxylic acid reacts with hydrazine to give the saturated 1,7-diphenyl-trans-phthalazin-4(3H)-one. The reaction of the acid with ethylenediamine yields diastereomeric trans-imidazo[2,3-a] isoindoles, which differ in their C-1 configuration. The cyclizations of the acid with cis-2-aminocyclohexane- or 4-cyclohexenemethanol result in trans-isoindolo[2,1-a][3,1]benzoxazines, while in its reactions with the analogous di-endo- and di-exo-norbornane- and -norborneneamino alcohols, the acid gives methylene-bridged isomeric di-endo-norbornanes or a norbornene derivative; the corresponding diastereomeric di-exo derivatives have also been prepared. After isolation, the structures were established by means of 1H and 13C NMR spectroscopy, with application of DIFFNOE, DEPT, HMQC, HMBC, and 2D-COSY techniques.

KW - Diastereomers

KW - DIFFNOE

KW - Isoindolones

KW - Methanobenzoxazinones

KW - NMR

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