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Imidazodipyridines via DMAP Catalyzed Domino N−H Carbonylation and 6π‐Electrocyclization: Synthetic Scope and Application
Author(s) -
Zhang Kena,
El Bouakher Abderrahman,
Lévaique Hélène,
Big Jérome,
Retailleau Pascal,
Alami Mouad,
Hamze Abdallah
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000553
Subject(s) - chemistry , domino , carbonylation , catalysis , pyridine , combinatorial chemistry , cascade reaction , organic chemistry , carbon monoxide
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 7 l exhibits good antiproliferative activity in the submicromolar range against the human colon cancer cell line.