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 journalArticlepeer-review

10 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, de-carboxylation reaction involving imidazo[1,2-a]pyridine, a secondary amine, and glyoxylic acid. The developed protocol re-quires mild reaction conditions and furnishes diverse imid-azo[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)
Pages (from-to)770-777
Number of pages8
JournalEuropean Journal of Organic Chemistry
Volume2019
Issue number4
DOIs
StatePublished - Jan 31 2019

Keywords

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

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Use of imidazo[1,2-a]pyridine as a carbonyl surrogate in a mannich-like, catalyst free, one-pot reaction'. Together they form a unique fingerprint.

Cite this