Stereoselectivity of cyclisations via N-acyliminium ions to form pyrido[2′,3′:3,4]pyrrolo[2,1-a]isoindole, -isoquinoline and -benz[c]azepine ring systems

Abood A. Bahajaj; John M. Vernon; Giles D. Wilson

doi:10.1039/B009316P

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Stereoselectivity of cyclisations via N-acyliminium ions to form pyrido[2′,3′:3,4]pyrrolo[2,1-a]isoindole, -isoquinoline and -benz[c]azepine ring systems

Abood A. Bahajaj,^a John M. Vernon*^a and Giles D. Wilson^a

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^a Department of Chemistry, University of York, Heslington, York, UK

Abstract

Pyrido[2′,3′:3,4]pyrrolo[2,1-a]isoindole, -isoquinoline and -benz[c]azepine derivatives are obtained by heating in polyphosphoric acid (PPA) appropriate hydroxy lactam precursors derived from pyridine-2,3-dicarboximides. The stereoselectivity of ring closure is rationalised by considering the development of A(1,3) strain in the cyclisation step from N-acyliminium ion intermediates.

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DOI: https://doi.org/10.1039/B009316P
Article type: Paper
Submitted: 20 Nov 2000
Accepted: 03 May 2001
First published: 30 May 2001

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J. Chem. Soc., Perkin Trans. 1, 2001, 1446-1451

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Stereoselectivity of cyclisations via N-acyliminium ions to form pyrido[2′,3′:3,4]pyrrolo[2,1-a]isoindole, -isoquinoline and -benz[c]azepine ring systems

A. A. Bahajaj, J. M. Vernon and G. D. Wilson, J. Chem. Soc., Perkin Trans. 1, 2001, 1446 DOI: 10.1039/B009316P

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Journal of the Chemical Society, Perkin Transactions 1

Stereoselectivity of cyclisations via N-acyliminium ions to form pyrido[2′,3′:3,4]pyrrolo[2,1-a]isoindole, -isoquinoline and -benz[c]azepine ring systems

Abstract

Article information

Download Citation

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Stereoselectivity of cyclisations via N-acyliminium ions to form pyrido[2′,3′:3,4]pyrrolo[2,1-a]isoindole, -isoquinoline and -benz[c]azepine ring systems

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