Silver-catalyzed cyclization of N-(prop-2-yn-1-yl)pyridin-2-amines

Mourad Chioua, Elena Soriano, Lourdes Infantes, M. Luisa Jimeno, José Marco-Contelles, Abdelouahid Samadi

Research output: Contribution to journalArticlepeer-review

47 Citations (Scopus)

Abstract

We report herein the silver-catalyzed cycloisomerization of readily available N-(prop-2-yn-1-yl)pyridine-2-amines as a new and practical method for the synthesis of differently substituted 3-methylimidazo[1,2-a]pyridines. The isomerization reactions proceeded under mild reactions conditions to give good yields and excellent regioselectivity. A DFT-based mechanistic analysis is also reported. The silver-catalyzed cycloisomerization of readily available N-(prop-2-yn-1-ylamino)pyridines is a new and practical method for the synthesis of differently substituted 3-methylimidazo[1,2-a]pyridines, suitable intermediates for further synthetic transformations and modulation, that proceeds under mild reaction conditions to give good-to-high yields and excellent regioselectivity.

Original languageEnglish
Pages (from-to)35-39
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number1
DOIs
Publication statusPublished - Jan 2013
Externally publishedYes

Keywords

  • Amines
  • Cyclization
  • Nitrogen heterocycles
  • Reaction mechanisms
  • Silver

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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