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Castanheiro T, Suffert J, Gulea M, et al. Aerobic Copper-Mediated Domino Three-Component Approach to 2-Aminobenzothiazole Derivatives. Org Lett. 2016;18(11):2588-91doi: 10.1021/acs.orglett.6b00967.
Castanheiro, T., Suffert, J., Gulea, M., & Donnard, M. (2016). Aerobic Copper-Mediated Domino Three-Component Approach to 2-Aminobenzothiazole Derivatives. Organic letters, 18(11), 2588-91. https://doi.org/10.1021/acs.orglett.6b00967
Castanheiro, Thomas, et al. "Aerobic Copper-Mediated Domino Three-Component Approach to 2-Aminobenzothiazole Derivatives." Organic letters vol. 18,11 (2016): 2588-91. doi: https://doi.org/10.1021/acs.orglett.6b00967
Castanheiro T, Suffert J, Gulea M, Donnard M. Aerobic Copper-Mediated Domino Three-Component Approach to 2-Aminobenzothiazole Derivatives. Org Lett. 2016 Jun 03;18(11):2588-91. doi: 10.1021/acs.orglett.6b00967. Epub 2016 May 18. PMID: 27192105.
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Org Lett. 2016 Jun 03;18(11):2588-91. doi: 10.1021/acs.orglett.6b00967. Epub 2016 May 18.

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

Organic letters

Thomas Castanheiro, Jean Suffert, Mihaela Gulea, Morgan Donnard

Affiliations

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

PMID: 27192105 DOI: 10.1021/acs.orglett.6b00967

Abstract

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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