Use of Imidazo[1,2‐a]pyridine as a Carbonyl Surrogate in a Mannich‐Like, Catalyst Free, One‐Pot Reaction

Abstract

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.

Antichagasic profile of a Series of Mannich Base‐Type Derivatives: Design, Synthesis, in vitro Evaluation, and Computational Studies Involving Iron Superoxide Dismutase

“…Mannich bases are versatile synthetic building blocks, which can be easily yielded into a range of potential derivatives to be employed in the field of medicinal chemistry . These derivatives have been synthesized through various methodologies described in the bibliography . A large number of Mannich base derivatives with potential antiparasitic activity have been reported .…”

“…[6][7] These derivatives have been synthesized through various methodologies described in the bibliography. [7][8][9][10][11] A large number of Mannich base derivatives with potential antiparasitic activity have been reported. [7,[12][13] In addition, our research group also reported the high potential trypanocidal activity of different Mannich bases.…”

Recent Developments in Transition‐Metal‐Catalyzed Regioselective Functionalization of Imidazo[1, 2‐a]pyridine

“…Functionalization of heterocyclic compounds is an important class of organic reactions due to their existence in a wide range of drugs, vitamins, natural products, biologically active molecules, etc [6] . Among the various heterocyclic compounds, imidazo[1, 2‐ a ]pyridine is the structural unit of a large number of natural and pharmaceutical products [7,8] . The methodology for the synthesis of this bio‐active scaffold includes cyclocondensations,oxidative couplings, rearrangements, C−H functionalizations,carbene‐transformations,multicomponent and tandem reactions among the different substrates [9–14] .…”