Reaction of β-lactam carbenes with 2-pyridyl isonitriles: a one-pot synthesis of 2-carbonyl-3-(pyridylamino)imidazo[1,2-a]pyridines useful as fluorescent probes for mercury ion

J Org Chem. 2011 Sep 16;76(18):7458-65. doi: 10.1021/jo201273p. Epub 2011 Aug 24.

Abstract

The one-pot reaction of β-lactam carbenes with 2-pyridyl isonitriles followed by an acidic hydrolysis was reported, which produced 2-carbonyl-3-(pyridylamino)imidazo[1,2-a]pyridines in moderate to good yields. Among the resulting novel imidazo[1,2-a]pyridine derivatives, 1-(6-chloro-3-(5-chloropyridin-2-ylamino)imidazo[1,2-a]pyridin-2-yl)-2-ethylbutan-1-one was demonstrated to be an efficient fluorescent probe for mercury ion both in acetonitrile and in buffered aqueous solution.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Fluorescent Dyes / chemistry*
  • Mercury / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Nitriles / chemistry*
  • Pyridines / chemistry*
  • beta-Lactams / chemistry*

Substances

  • Fluorescent Dyes
  • Nitriles
  • Pyridines
  • beta-Lactams
  • carbene
  • Mercury
  • Methane