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Synthesis 2015; 47(24): 3983-3989
DOI: 10.1055/s-0035-1560089
DOI: 10.1055/s-0035-1560089
paper
Domino 6-endo-dig Cyclization/Halogenation Reactions: Three-Component Synthesis of 1,3-Disubstituted 4-Haloimidazo[1,2-a:4,5-c′]dipyridines
Further Information
Publication History
Received: 22 May 2015
Accepted after revision: 11 July 2015
Publication Date:
11 September 2015 (online)
Abstract
A regiocontrolled 6-endo-dig cyclization of 3-ethynylimidazo[1,2-a]pyridine-2-carbonitriles promoted by Grignard reagent in the presence of iodine has been developed. We optimized the reaction conditions to allow the straightforward synthesis of 1,3-disubstituted 4-iodoimidazo[1,2-a:4,5-c′]dipyridines. Finally, the reactivity of the 4-iodo position toward various metal-catalyzed coupling reactions (Suzuki–Miyaura, Sonogashira, etc.) or cyanation was successfully evaluated.
Key words
heterocycles - polycycles - cyclizations - Suzuki–Miyaura reactions - Sonogashira reactions - cyanationsSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560089.
- Supporting Information
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