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Use of Imidazo[1,2‐ a ]pyridine as a Carbonyl Surrogate in a Mannich‐Like, Catalyst Free, One‐Pot Reaction
Author(s) -
Naresh Gunaganti,
Lakkaniga Naga Rajiv,
Kharbanda Anupreet,
Yan Wei,
Frett Brendan,
Li Hongyu
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801430
Subject(s) - chemistry , pyridine , imidazopyridine , catalysis , combinatorial chemistry , amine gas treating , organic chemistry , reagent , mannich reaction , decarboxylation , derivatization , high performance liquid chromatography
Derivatization of imidazo[1,2‐ a ]pyridine scaffolds have gained considerable attention due to the biological significance of therapeutics based on the imidazopyridine core. By utilizing a catalyst‐free, “Mannich type” reaction, we developed a simple and efficient protocol to aminomethylate the C‐3 position of imidazo[1,2‐ a ]pyridine through a multicomponent, decarboxylation reaction involving imidazo[1,2‐ a ]pyridine, a secondary amine, and glyoxylic acid. The developed protocol requires mild reaction conditions and furnishes diverse imidazo[1,2‐ a ]pyridine analogues from commercially available starting materials. Additionally, the current protocol improves prior methods, which were limited by the amine substrate scope. Taken together, this current methodology permits rapid diversification of imidazo[1,2‐ a ]pyridines to enhance combinatorial efficiency in the drug discovery processes.