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J Org Chem. 2016 Dec 16;81(24):12472-12477. doi: 10.1021/acs.joc.6b02315. Epub 2016 Dec 06.

Exploring the Reactivity of 2-Trichloromethylbenzoxazoles for Access to Substituted Benzoxazoles.

The Journal of organic chemistry

Roy P Lester, Travis Bham, Thomas W Bousfield, William Lewis, Jason E Camp

Affiliations

  1. School of Chemistry, University of Nottingham , Nottingham NG7 2RD, United Kingdom.
  2. Department of Chemical Sciences, University of Huddersfield , Queensgate, Huddersfield, HD1 3DH, United Kingdom.

PMID: 27978741 DOI: 10.1021/acs.joc.6b02315

Abstract

The reactivity of 2-trichloromethylbenzoxazoles toward various nucleophiles, under metal-free or iron-catalyzed conditions, for the synthesis of substituted benzoxazoles is described. These methods allow for selective substitution at either the 2- or 2'-position of the benzoxazoles using the same starting materials/reagents. This approach allows for the controlled synthesis of a variety of key derivatives from a single 2-trichloromethylbenzoxazole starting material.

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