Base-Promoted Domino Reaction of 5-Substituted 2-Nitrosophenols with Bromomethyl Aryl Ketones: A Transition-Metal-Free Approach to 2-Aroylbenzoxazoles

Publication Type: Journal contribution (peer reviewed)
Authors: Aljaar, N.; Malakar, C. C.; Conrad, J.; Beifuss U.
Year of publication: 2015
Published in: J. Org. Chem.
Band/Volume: 80/
DOI: 10.1021/acs.joc.5b02000
Page (from - to): 10829-10837

Abstract

The reaction of 5-substituted 2-nitrosophenols with bromomethyl aryl ketones and related compounds employing K₂CO₃ as a base in refluxing THF and DMF at 80 °C, respectively, delivers 2-aroylbenzoxazoles in a single step with yields up to 85%. The new method involves an intermolecular nucleophilic substitution followed by intramolecular 1,2-addition and elimination. It allows an efficient and practical access to 2-aroylbenzoxazoles under transition-metal-free conditions.

Involved persons

Dr. rer. nat. Jürgen Conrad
Prof. Dr. rer. nat. Uwe Beifuß

Involved institutions

Bioorganic Chemistry
Institute of Chemistry