Electrophilic cyclization of o-acetoxy- and o-benzyloxyalkynylpyridines: an easy entry into 2,3-disubstituted furopyridines

Antonio Arcadi; Sandro Cacchi; Sabrina Di Giuseppe; Giancarlo Fabrizi; Fabio Marinelli

doi:10.1021/ol0261581

Electrophilic cyclization of o-acetoxy- and o-benzyloxyalkynylpyridines: an easy entry into 2,3-disubstituted furopyridines

Org Lett. 2002 Jul 11;4(14):2409-12. doi: 10.1021/ol0261581.

Authors

Antonio Arcadi¹, Sandro Cacchi, Sabrina Di Giuseppe, Giancarlo Fabrizi, Fabio Marinelli

Affiliation

¹ Dipartimento di Chimica Ingegneria Chimica e Materiali della Facoltà di Scienze, Università di L'Aquila, Via Vetoio, Coppito Due, I-67100 L'Aquila, Italy. arcadi@univaq.it

PMID: 12098259
DOI: 10.1021/ol0261581

Abstract

[reaction: see text] 2,3-Disubstituted furo[3,2-b]pyridines, 2,3-disubstituted furo[2,3-b]pyridines, and 2,3-disubstituted furo[2,3-c]pyridines are readily prepared under mild conditions via the palladium-catalyzed cross-coupling of 1-alkynes with o-iodoacetoxy- or o-iodobenzyloxypyridines, followed by electrophilic cyclization by I(2) or by PdCl(2) under a balloon of carbon monoxide.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyclization
Furans / chemical synthesis*
HIV Protease Inhibitors / chemical synthesis*
Indicators and Reagents
Pyridines / chemical synthesis*

Substances

Furans
HIV Protease Inhibitors
Indicators and Reagents
Pyridines