Cu-Mediated Expeditious Annulation of Alkyl 3-Aminoacrylates with Aryldiazonium Salts: Access to Alkyl N2-Aryl 1,2,3-Triazole-carboxylates for Druglike Molecular Synthesis

• DOI: 10.1021/acs.orglett.0c00006
• Publication Date: 2020-02-04T14:21:06Z
• Authors: Hao-Nan Liu; Hao-Qiang Cao; Chi Wai Cheung; Jun-An Ma
• Keywords: Annulation; 1,2,3-Triazole; Triazole

Alkyl N-aryl 1,2,3-triazole-carboxylates are important molecules or intermediates in medicinal chemistry, but the synthesis of N2-aryl counterparts remains elusive. Herein, we describe a Cu-mediated annulation reaction alkyl 3-aminoacrylates with aryldiazonium salts, both which readily available substrates. Furthermore, 2-aminoacrylates also viable Diverse and their analogues can be rapidly prepared under mild conditions. Especially, this protocol allows one to access several druglike variants carbonic anhydrase inhibitors celecoxib.