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One-pot synthesis of tetracyclic fused imidazo[1,2- a ]pyridines via a three-component reaction

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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.

No MeSH data available.


MCR to polycyclic fused imidazo[1,2-a]pyridine derivatives.
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C1: MCR to polycyclic fused imidazo[1,2-a]pyridine derivatives.

Mentions: In view of the significance of the GBB reaction and the imidazo[1,2-a]pyridine core structure, the further development of new GBB-based methods for the efficient synthesis of novel polycyclic fused imidazo[1,2-a]pyridines is highly desirable. In an earlier study, we have developed a GBB/lactamization MCR strategy, which provided the rapid access to isoquinolinone-fused imidazo[1,2-a]pyridines with potent and selective CDK2 inhibition properties [34–35]. As a continuing effort, we report herein our recent efforts in the development of a GBB-based MCR method for the one-pot synthesis of diverse quinazolin-2-one fused imidazo[1,2-a]pyridines (Scheme 1). Parts of the work have been disclosed in a previous patent [36].


One-pot synthesis of tetracyclic fused imidazo[1,2- a ]pyridines via a three-component reaction
MCR to polycyclic fused imidazo[1,2-a]pyridine derivatives.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC4979633&req=5

C1: MCR to polycyclic fused imidazo[1,2-a]pyridine derivatives.
Mentions: In view of the significance of the GBB reaction and the imidazo[1,2-a]pyridine core structure, the further development of new GBB-based methods for the efficient synthesis of novel polycyclic fused imidazo[1,2-a]pyridines is highly desirable. In an earlier study, we have developed a GBB/lactamization MCR strategy, which provided the rapid access to isoquinolinone-fused imidazo[1,2-a]pyridines with potent and selective CDK2 inhibition properties [34–35]. As a continuing effort, we report herein our recent efforts in the development of a GBB-based MCR method for the one-pot synthesis of diverse quinazolin-2-one fused imidazo[1,2-a]pyridines (Scheme 1). Parts of the work have been disclosed in a previous patent [36].

View Article: PubMed Central - HTML - PubMed

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.

No MeSH data available.