Cascade carbopalladation-annulation approach toward polycylic derivatives of indole and indolizine.

Authors:
Natalia Chernyak
Natalia Chernyak
University of Illinois at Chicago
United States
David Tilly
David Tilly
Griffith University
Australia
Zhou Li
Zhou Li
Institute of Otolaryngology
China
Vladimir Gevorgyan
Vladimir Gevorgyan
Tohoku University
Japan

ARKIVOC 2010 Dec;2011(5):76-91

A convenient method for construction of polycyclic fused nitrogen-containing heterocycles has been developed. The methodology involves palladium-catalyzed intermolecular carbopalladation-annulation cascade reaction of haloaryl heterocyclic derivatives with different alkynes under relatively mild reaction conditions. Thus, the palladium-catalyzed cascade cyclization of bromophenyl derivatives of indolizine and indole with alkynes afforded tetracycles, possessing a newly formed fused six-membered ring. The reaction of 3-(2-iodobenzyl)-indoles with a variety of alkynes afforded polycyclic compounds with fused seven-membered rings. Annulation with unsymmetrical alkynes exhibited varied regioselectivity. Overall, this approach allows for quick and efficient assembly of polycyclic derivatives of indole and indolizine from easily available precursors.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3909657PMC
December 2010
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