Issue 3, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

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

Géza Stájer,‡*a   Angela E. Szabó,a   Ferenc Csende,a   Gyula Argayb  and  Pál Sohár*c  

* Corresponding authors

a Institute of Pharmaceutical Chemistry, University of Szeged, P.O. Box 121, H-6701 Szeged, Hungary
E-mail: Stajer@pharma.szote.u-szeged.hu
Fax: (62)545-705

b Central Research Institute for Chemistry, Hungarian Academy of Sciences, P.O. Box 17, H-1525 Budapest-114, Hungary

c Research Group for Structural Chemistry and Spectroscopy, Hungarian Academy of Sciences—Eötvös Loránd University and Department of General and Inorganic Chemistry, Eötvös Loránd University, P.O. Box 32, H-1518 Budapest-112, Hungary

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.

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

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Article information

DOI
https://doi.org/10.1039/B107293P
Article type
Paper
Submitted
10 Aug 2001
Accepted
07 Jan 2002
First published
04 Feb 2002

J. Chem. Soc., Perkin Trans. 2, 2002, 657-662

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

G. Stájer, A. E. Szabó, F. Csende, G. Argay and P. Sohár, J. Chem. Soc., Perkin Trans. 2, 2002, 657 DOI: 10.1039/B107293P

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