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Domino 6-endo-dig Cyclization/Halogenation Reactions: Three-Component Synthesis of 1,3-Disubstituted 4-Haloimidazo[1,2-a:4,5-c′]dipyridines

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.
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https://hal-univ-tours.archives-ouvertes.fr/hal-02389894
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Submitted on : Monday, December 2, 2019 - 5:05:44 PM
Last modification on : Tuesday, September 13, 2022 - 4:59:32 PM

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Cécile Enguehard-Gueiffier, Pierre-Olivier Delaye, Mélanie Pénichon, Caroline Denevault-Sabourin, Hassan Allouchi, et al.. Domino 6-endo-dig Cyclization/Halogenation Reactions: Three-Component Synthesis of 1,3-Disubstituted 4-Haloimidazo[1,2-a:4,5-c′]dipyridines. Synthesis: Journal of Synthetic Organic Chemistry, 2015, 47 (24), pp.3983-3989. ⟨10.1055/s-0035-1560089⟩. ⟨hal-02389894⟩

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