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Synthesis 2010(22): 3927-3933  
DOI: 10.1055/s-0030-1258247
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Arylation of 2-Furyl 4-Fluorophenyl Ketone: An Extension of Heck Chemistry towards Novel Integrase Inhibitors

Luigi Franchia, Marta Rinaldia, Giulia Vignarolia, Anna Innitzera, Marco Radia, Maurizio Botta*a,b
a Dipartimento Farmaco Chimico Tecnologico, University of Siena, Via Alcide de Gasperi 2, 53100 Siena, Italy
b Sbarro Institute for Cancer Research and Molecular Medicine, Center for Biotechnology, College of Science and Technology, Temple University, BioLife Science Bldg., Suite 333, 1900 N 12th Street, Philadelphia, PA 19122, USA
Fax: +39(577)234306; e-Mail: botta.maurizio@gmail.com;
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Publikationsverlauf

Received 28 July 2010
Publikationsdatum:
07. September 2010 (online)

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Abstract

An optimized procedure for the direct and regioselective arylation of 2-acylfurans has been developed. The versatility of this protocol has been evaluated on a series of aryl and heteroaryl halides, thus obtaining a small collection of 2,5-disubstituted furans in moderate to good yields. Finally, the optimized protocol has been successfully applied to the synthesis of the HIV-1 integrase inhibitor 3 and could be further exploited for the generation of novel substituted furans as potential integrase inhibitors.

Key words

Heck reaction - direct arylation - 2-acylfurans - catalysis - integrase inhibitors

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