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

Cécile Enguehard-Gueiffier (1) , Pierre-Olivier Delaye (2) , Mélanie Pénichon (2) , Caroline Denevault-Sabourin (2) , Hassan Allouchi (2) , Alain Gueiffier (1)

1 N2C - Nutrition, croissance et cancer (U 1069)
2 UMR ISP - Infectiologie et Santé Publique

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.

Keywords: heterocycles; polycycles; cyclizations; Suzuki-Miyaura reactions; Sonogashira reactions

Keywords: cyanations

Domains: Chemical Sciences; Organic chemistry

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⟩