Abstract
A novel three-component reaction has been developed to assemble biologically and pharmaceutically important tetracyclic fused imidazo[1,2-a]pyridines in a one-pot fashion utilizing readily available 2-aminopyridines, isatins and isocyanides. The three-component coupling proceeds through the Groebke–Blackburn–Bienaymé reaction followed by a retro-aza-ene reaction and subsequent nucleophilic reaction of the in-situ generated imidazo[1,2-a]pyridines bearing an isocyanate functional group.
Highlights
Multicomponent reactions (MCRs) have attracted considerable attention in organic and medicinal chemistry due to their high efficiency, simple operability, atom economy and unmatched versatility [1,2,3,4,5,6]
The imidazo[1,2-a]pyridine scaffolds can be constructed in great diversity by a multicomponent reaction of amidines, aldehydes and isocyanides
We have developed a GBB/lactamization MCR strategy, which provided the rapid access to isoquinolinonefused imidazo[1,2-a]pyridines with potent and selective CDK2 inhibition properties [34,35]
Summary
Multicomponent reactions (MCRs) have attracted considerable attention in organic and medicinal chemistry due to their high efficiency, simple operability, atom economy and unmatched versatility [1,2,3,4,5,6] These reactions serve as an ideal synthetic tool for the assembly of structurally diverse and biologically relevant heterocycles, and have been extensively investigated by organic and medicinal chemists to explore lead compounds in drug discovery efforts [7,8,9,10]. The imidazo[1,2-a]pyridine scaffolds can be constructed in great diversity by a multicomponent reaction of amidines, aldehydes and isocyanides. Scheme 1: MCR to polycyclic fused imidazo[1,2-a]pyridine derivatives
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