Imidazodipyridines via DMAP Catalyzed Domino N−H Carbonylation and 6π‐Electrocyclization: Synthetic Scope and Application. Issue 15 (9th July 2020)

• Record Type: Journal Article
• Authors: Zhang, Kena; El Bouakher, Abderrahman; Lévaique, Hélène; Bignon, Jérome; Retailleau, Pascal; Alami, Mouad; Hamze, Abdallah
• Is Part Of: Advanced synthesis & catalysis. Volume 362:Issue 15(2020)
• Page Start: 3243
• Page End: 3256
• Publication Date: 2020-07-09
• Subjects: Imidazodipyridines -- Domino reaction -- 6π-electrocyclization -- DMAP -- antiproliferative activity; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202000553
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: In this work, we report a domino reaction for access to highly functionalized imidazo[1, 2‐ a :5, 4‐ b′ ]dipyridines simply by stirring Boc2 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 7 l exhibits good antiproliferative activity in the submicromolar range against the human colon cancer cell line. Abstract :