Imidazodipyridines via DMAP Catalyzed Domino N-H Carbonylation and 6 pi-Electrocyclization: Synthetic Scope and Application

摘要

In this work, we report a domino reaction for access to highly functionalized imidazo[1,2-a:5,4-b']dipyridines simply by stirring Boc(2)O in the presence of DMAP as a catalyst with readily prepared 3-amino-2-(vinyl)imidazo[1,2-a]pyridine. This methodology enables the synthesis of highly functionalized imidazodipyridines. The process proved to be compatible with a wide variety of substrates. The synthetic potential of this method was illustrated by performing a Suzuki-Miyaura coupling on 4-phenylimidazo-dipyridin-2-ol derivatives. Screening of the biological activity of the newly generated compounds led to the identification of a new hit. Compound 71 exhibits good antiproliferative activity in the submicromolar range against the human colon cancer cell line.