Sustainable Synthetic Approaches for 3‐Aminoimidazo‐fused Heterocycles via Groebke‐Blackburn‐Bienaymé Process

Two different sustainable and efficient synthetic methods have been developed for the synthesis of a variety of 3‐aminoimidazo fused heterocycles by one‐pot three component reaction of 2‐aminoazines, aldehydes and isocyanides. The methods adopted were (a) aqueous micellar mediated condition (method...

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Bibliographic Details
Published in:ChemistrySelect (Weinheim) 2020-09, Vol.5 (34), p.10637-10642
Main Authors: Mathavan, Sivagami, B. R. D. Yamajala, Rajesh
Format: Article
Language:English
Subjects:
3-Aminoimidazo fused heterocycle
Groebke-Blackburn-Bienaymé reaction
Multicomponent reaction
Surfactant
Thiamine hydrochloride
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Summary:Two different sustainable and efficient synthetic methods have been developed for the synthesis of a variety of 3‐aminoimidazo fused heterocycles by one‐pot three component reaction of 2‐aminoazines, aldehydes and isocyanides. The methods adopted were (a) aqueous micellar mediated condition (method A) (b) VB1 catalyzed reaction under solvent‐free condition (method B). Excellent yields were obtained for a broad range of biologically significant imidazopyridine core molecules under green conditions at room temperature. Synthesis in aqueous micellar medium, mild reaction conditions, organocatalyst, easy work‐up and isolation, and gram scale synthesis, are some of the advantages of these protocols. A diverse series of imidazo[1,2‐a]pyridine derivatives were synthesized from the isocyanide based three component reaction, the G−B‐B reaction, with a wide variety of 2‐aminopyridines, aromatic, aliphatic as well as heteroaromatic aldehydes and isocyanides using two mild, environmental‐friendly, and efficient protocols with excellent yields.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.202002894