Efficient Synthesis
of Tetrahydro-β-carbolin-1-one and Dihydroisoquinolin-1-one
Derivatives as Versatile Intermediates

Katie E. Judd; Mary F. Mahon; Lorenzo Caggiano

doi:10.1055/s-0029-1216904

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Synthesis 2009(16): 2809-2817
DOI: 10.1055/s-0029-1216904

FEATUREARTICLE

Efficient Synthesis of Tetrahydro-β-carbolin-1-one and Dihydroisoquinolin-1-one Derivatives as Versatile Intermediates

Katie E. Judd^a, Mary F. Mahon^b, Lorenzo Caggiano*^a
^a Wolfson Laboratory of Medicinal Chemistry, Department of Pharmacy and Pharmacology, University of Bath, Claverton Down, Bath, BA2 7AY, UK
Fax: +44(1225)386114; e-Mail: l.caggiano@bath.ac.uk;
^b X-ray Crystallography Unit, Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, UK

Further Information

Publication History

Received 27 April 2009
Publication Date:
14 July 2009 (online)

Abstract
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Abstract

An efficient one-pot procedure is described in which an isocyanate intermediate, generated from the corresponding carboxylic acid by a modified Curtius rearrangement, is captured by a tethered aromatic ring in the presence of BF₃˙OEt₂ to generate various lactams, including tetrahydro-β-carbolin-1-one and dihydroisoquinolin-1-one derivatives.

Key words

cyclizations - heterocycles - lactams - Lewis acids - rearrangements

References

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Prolonged exposure to DMSO results in decomplexation.

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Crystallographic data for compounds 1a and 2d have been deposited with the Cambridge Crystallographic Data Centre as supplementary publications CCDC 728651 and 728652, respectively. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK. Fax +44(1223)336033, e-mail: deposit@ccdc.cam.ac.uk.