Application of t-2-benzoyl-t-5-phenylcyclohexane-r-1-carboxylic acid for the preparation of saturated isoindole-fused heterocycles

Géza Stájer, Angela E. Szabó, Ferenc Csende, Gyula Argay, Pál Sohár

Research output: Article

6 Citations (Scopus)

Abstract

t-2-Benzoyl-t-5-phenylcyclohexane-r-1-carboxylic acid 1 reacts with cis-2-aminocyclohexanemethanol to give the saturated cis-isoindolo[2,1-a][3,1]benzoxazine 2. Reaction of 1 with trans-2-aminocyclohex-4-enemethanol yields three diastereomeric isoindolo derivatives 3a-c. Cyclization of 1 with 1,3-diaminopropane results in a diastereomeric mixture of cis-pyrimido[1,2-a]isoindolones 4a,b. With di-endo-norbornane aminoalcohol, 1 reacts to yield a mixture of cis- and trans-annelated diastereomers 5 and 6. In its reactions with di-exo-norbornane and norbornene aminoalcohols, 1 isomerizes to give cis-condensed isoindolo derivatives 7-10. After isolation, the structures were established by 1H and 13C NMR spectroscopy, with up-to-date measuring techniques such as NOEDIF, DEPT, HMQC, 2D-NOESY, 2D-COSY and HMBC and, for 10, X-ray measurements. The results show that, with two exceptions, the trans acid 1 undergoes isomerization to give cis-condensed products.

Original languageEnglish
Pages (from-to)657-662
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number3
Publication statusPublished - 2002

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Norbornanes
Isoindoles
Carboxylic Acids
Benzoxazines
Derivatives
Cyclization
Isomerization
Nuclear magnetic resonance spectroscopy
X rays
Acids
phenylcyclohexane

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Application of t-2-benzoyl-t-5-phenylcyclohexane-r-1-carboxylic acid for the preparation of saturated isoindole-fused heterocycles",
abstract = "t-2-Benzoyl-t-5-phenylcyclohexane-r-1-carboxylic acid 1 reacts with cis-2-aminocyclohexanemethanol to give the saturated cis-isoindolo[2,1-a][3,1]benzoxazine 2. Reaction of 1 with trans-2-aminocyclohex-4-enemethanol yields three diastereomeric isoindolo derivatives 3a-c. Cyclization of 1 with 1,3-diaminopropane results in a diastereomeric mixture of cis-pyrimido[1,2-a]isoindolones 4a,b. With di-endo-norbornane aminoalcohol, 1 reacts to yield a mixture of cis- and trans-annelated diastereomers 5 and 6. In its reactions with di-exo-norbornane and norbornene aminoalcohols, 1 isomerizes to give cis-condensed isoindolo derivatives 7-10. After isolation, the structures were established by 1H and 13C NMR spectroscopy, with up-to-date measuring techniques such as NOEDIF, DEPT, HMQC, 2D-NOESY, 2D-COSY and HMBC and, for 10, X-ray measurements. The results show that, with two exceptions, the trans acid 1 undergoes isomerization to give cis-condensed products.",
author = "G{\'e}za St{\'a}jer and Szab{\'o}, {Angela E.} and Ferenc Csende and Gyula Argay and P{\'a}l Soh{\'a}r",
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T1 - Application of t-2-benzoyl-t-5-phenylcyclohexane-r-1-carboxylic acid for the preparation of saturated isoindole-fused heterocycles

AU - Stájer, Géza

AU - Szabó, Angela E.

AU - Csende, Ferenc

AU - Argay, Gyula

AU - Sohár, Pál

PY - 2002

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N2 - t-2-Benzoyl-t-5-phenylcyclohexane-r-1-carboxylic acid 1 reacts with cis-2-aminocyclohexanemethanol to give the saturated cis-isoindolo[2,1-a][3,1]benzoxazine 2. Reaction of 1 with trans-2-aminocyclohex-4-enemethanol yields three diastereomeric isoindolo derivatives 3a-c. Cyclization of 1 with 1,3-diaminopropane results in a diastereomeric mixture of cis-pyrimido[1,2-a]isoindolones 4a,b. With di-endo-norbornane aminoalcohol, 1 reacts to yield a mixture of cis- and trans-annelated diastereomers 5 and 6. In its reactions with di-exo-norbornane and norbornene aminoalcohols, 1 isomerizes to give cis-condensed isoindolo derivatives 7-10. After isolation, the structures were established by 1H and 13C NMR spectroscopy, with up-to-date measuring techniques such as NOEDIF, DEPT, HMQC, 2D-NOESY, 2D-COSY and HMBC and, for 10, X-ray measurements. The results show that, with two exceptions, the trans acid 1 undergoes isomerization to give cis-condensed products.

AB - t-2-Benzoyl-t-5-phenylcyclohexane-r-1-carboxylic acid 1 reacts with cis-2-aminocyclohexanemethanol to give the saturated cis-isoindolo[2,1-a][3,1]benzoxazine 2. Reaction of 1 with trans-2-aminocyclohex-4-enemethanol yields three diastereomeric isoindolo derivatives 3a-c. Cyclization of 1 with 1,3-diaminopropane results in a diastereomeric mixture of cis-pyrimido[1,2-a]isoindolones 4a,b. With di-endo-norbornane aminoalcohol, 1 reacts to yield a mixture of cis- and trans-annelated diastereomers 5 and 6. In its reactions with di-exo-norbornane and norbornene aminoalcohols, 1 isomerizes to give cis-condensed isoindolo derivatives 7-10. After isolation, the structures were established by 1H and 13C NMR spectroscopy, with up-to-date measuring techniques such as NOEDIF, DEPT, HMQC, 2D-NOESY, 2D-COSY and HMBC and, for 10, X-ray measurements. The results show that, with two exceptions, the trans acid 1 undergoes isomerization to give cis-condensed products.

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