Iron-Mediated One-Pot Synthesis of 3,5-Diarylpyridines from β-Nitrostyrenes

J Org Chem. 2016 Mar 4;81(5):2159-65. doi: 10.1021/acs.joc.5b02712. Epub 2016 Feb 12.

Abstract

An operationally simple and mild one-pot protocol for the synthesis of a variety of 3,5-diarylpyridines from β-nitrostyrenes was achieved by using elemental iron. This reaction proceeds via reduction of the nitro group, resulting in in situ imine formation followed by trimolecular condensation with concomitant debenzylative aromatization. By employing this method, a series of symmetrical and unsymmetrical 3,5-diarylpyridines were synthesized with good to excellent yields. In addition, this method was also utilized for the synthesis of Sch-21418, an anti-inflammatory agent on gram scale.

Publication types

  • Research Support, Non-U.S. Gov't