A facile synthesis of dibenzopyrroloazepinones as tetracyclic allocolchicinoids--an unusual 1,2-phenyl shift

Liang Wu; Abil E Aliev; Stephen Caddick; Richard J Fitzmaurice; Derek A Tocher; Frank D King

doi:10.1039/b919114c

A facile synthesis of dibenzopyrroloazepinones as tetracyclic allocolchicinoids--an unusual 1,2-phenyl shift

Chem Commun (Camb). 2010 Jan 14;46(2):318-20. doi: 10.1039/b919114c. Epub 2009 Nov 30.

Authors

Liang Wu¹, Abil E Aliev, Stephen Caddick, Richard J Fitzmaurice, Derek A Tocher, Frank D King

Affiliation

¹ Department of Chemistry, University College London, 20 Gordon Street, London, UK WC1H 0AJ.

PMID: 20024364
DOI: 10.1039/b919114c

Abstract

A facile synthesis of dibenzopyrroloazepinones via an electrophilic cyclisation of a biphenyl-acyliminium ion is described; an unusual 1,2-phenyl shift occurs when the C-1' carbon is the more nucleophilic than the C-2' carbon.

MeSH terms

Azepines / chemical synthesis
Azepines / chemistry*
Biphenyl Compounds / chemistry*
Carbazoles / chemical synthesis
Carbazoles / chemistry*
Colchicine / chemistry*
Crystallography, X-Ray
Cyclization
Molecular Conformation

Substances

Azepines
Biphenyl Compounds
Carbazoles
carbazole
diphenyl
Colchicine