Aerobic Copper-Mediated Domino Three-Component Approach to 2-Aminobenzothiazole Derivatives.

Org Lett

Laboratoire d'Innovation Thérapeutique (UMR 7200), Faculté de Pharmacie, Université de Strasbourg, CNRS , 74 Route du Rhin, 67401 Illkirch, France.

Published: June 2016

An unprecedented three-component reaction involving a 2,2'-diaminodiaryl disulfide, copper cyanide, and an electrophile is described. This transformation is based on an oxidative copper-mediated S-cyanation as a key step and involves a cyanation/cyclization/acylation domino sequence enabling a rapid and efficient synthesis of diversely substituted 2-aminobenzothiazole derivatives. Notably, this reaction proceeds via an original mechanism involving an intermolecular migration of the acyl group.

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http://dx.doi.org/10.1021/acs.orglett.6b00967DOI Listing

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