Journal
TETRAHEDRON LETTERS
Volume 54, Issue 39, Pages 5378-5382Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.07.113
Keywords
Imidazo[1,2-a]pyridines; 2-Chloro-3-nitroimidazo[1,2-a]pyridine; Suzuki-Miyaura reaction; Buchwald-Hartwig amination; Ullmann amination
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Funding
- Region des Pays de la Loire
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Alternative strategies for functionalizing 2-chloro-3-nitroimidazo[1,2-a]pyridine have been developed. Suzuki-Miyaura cross-coupling reaction provided easily the corresponding 2-arylated compounds, and herefrom the nitro group was reduced into amine which afforded amides, anilines, and ureas in the 3-position. The amination of the key compound using a metal-catalyzed reaction was reported. This study highlighted the importance of the nitro group to facilitate the chlorine displacement. Other nucleophilic aromatic substitutions open a route to various products derived from imidazo[1,2-a]pyridine. (c) 2013 Elsevier Ltd. All rights reserved.
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