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A Base Promoted Cyclization of N-Propargylaminopyridines. Synthesis of Imidazo[1,2-a]pyridine Derivatives

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Suren Husinec^†, Rade Markovic^‡, Milos Petkovic^§, Veselin Nasufovic^§, and Vladimir Savic ^§

Institute of Chemistry, Technology and Metallurgy, Centre for Chemistry, P.O. Box 815, Njegoseva 12, 11000 Belgrade, Serbia, University of Belgrade, Faculty of Chemistry, Studentski Trg 12-16, 11000 Belgrade, Serbia, and University of Belgrade, Faculty of Pharmacy, Vojvode Stepe 450, 11221 Belgrade, Serbia

Org. Lett., 2011, 13 (9), pp 2286–2289

DOI: 10.1021/ol200508x

Publication Date (Web): March 29, 2011

vladimir.savic@pharmacy.bg.ac.rs, †

Institute of Chemistry, Technology and Metallurgy.

, ‡

University of Belgrade, Faculty of Chemistry.

, §

University of Belgrade, Faculty of Pharmacy.

Section:

Heterocyclic Compounds (More than One Hetero Atom)

Abstract

A base promoted cyclization of the protected N-propargylaminopyridines was shown to be an efficient method for the preparation of imidazo[1,2-a]pyridine derivatives. The reactions were carried out with a small excess of base, at room temperature or slightly above producing the heterocyclic products in moderate to good yields. The stereoelectronic properties of substituents on the pyridine ring were shown to influence the cyclization process.

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