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

Gunaganti Naresh, Naga Rajiv Lakkaniga, Anupreet Kharbanda, Wei Yan, Brendan Frett, Hong Yu Li

Research output: Contribution to journalArticle

6 Scopus citations

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.

Original languageEnglish (US)
JournalEuropean Journal of Organic Chemistry
DOIs
StateAccepted/In press - Jan 1 2019
Externally publishedYes

Keywords

  • Aminomethylation
  • Catalyst-free reaction
  • Heterocycles
  • Mannich bases
  • Multicomponent reactions

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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