Regiocontrolled Microwave Assisted Bifunctionalization of 7,8-Dihalogenated Imidazo1,2-apyridines: A One Pot Double-Coupling ApproachReportar como inadecuado




Regiocontrolled Microwave Assisted Bifunctionalization of 7,8-Dihalogenated Imidazo1,2-apyridines: A One Pot Double-Coupling Approach - Descarga este documento en PDF. Documentación en PDF para descargar gratis. Disponible también para leer online.

Recherche et Innovation en Chimie Médicinale, UMR INRA 1282 Infectiologie et Santé Publique, Université F. Rabelais, 31 avenue Monge, F-37200 Tours, France





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Abstract The reactivity of the 7-chloro-8-iodo- and 8-chloro-7-iodoimidazo1,2-apyridines 1a–e diversely substituted on the 2 position, towards Suzuki-Miyaura, Sonogashira, and Buchwald-Hartwig cross-coupling reactions as well as cyanation was evaluated. Various methodologies are proposed to introduce aryl, heteroaryl, alkyne, amine or cyano groups in the two positions depending on the nature of the substituent present in position 2. In both series, the substitution of the iodine atom was totally regioselective and the difficulty was to substitute the chlorine atom in a second step. Until now, only heteroaryl groups could be introduced though Suzuki-Miyaura cross-coupling. We overcame this problem evaluating both regioisomers in parallel. The double coupling approach was also studied allowing the one pot Suzuki-Suzuki, cyanation-Sonogashira and cyanation-Buchwald reactions leading to polyfunctionnalized imidazo1,2-apyridines.

Keywords: imidazo1,2-apyridine; metallo-catalyzed cross-coupling reaction; microwave irradiation; Suzuki-Miyaura cross-coupling; Sonogashira cross-coupling; cyanation; Buchwald-Hartwig cross-coupling imidazo1,2-apyridine; metallo-catalyzed cross-coupling reaction; microwave irradiation; Suzuki-Miyaura cross-coupling; Sonogashira cross-coupling; cyanation; Buchwald-Hartwig cross-coupling





Autor: Emilie Marie, Sébastien Bouclé, Cécile Enguehard-Gueiffier * and Alain Gueiffier

Fuente: http://mdpi.com/



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