Cu-Mediated Expeditious Annulation of Alkyl 3-Aminoacrylates with Aryldiazonium Salts: Access to Alkyl <i>N</i><sup>2</sup>-Aryl 1,2,3-Triazole-carboxylates for Druglike Molecular Synthesis
Hao-Nan Liu, Hao‐Qiang Cao, Chi Wai Cheung, Jun‐An Ma
Abstract
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 of alkyl 3-aminoacrylates with aryldiazonium salts, both of which are readily available substrates. Furthermore, alkyl 2-aminoacrylates are also viable substrates. Diverse alkyl N2-aryl 1,2,3-triazole-carboxylates and their analogues can be rapidly prepared under mild conditions. Especially, this protocol allows one to access several druglike variants of carbonic anhydrase inhibitors and celecoxib.
Topics & Concepts
AlkylChemistryArylAnnulation1,2,3-TriazoleTriazoleCombinatorial chemistryMoleculeMedicinal chemistryOrganic chemistryCatalysisClick Chemistry and ApplicationsSynthesis and Catalytic ReactionsCyclopropane Reaction Mechanisms