Communications

Synthesis of a library of 2-aryl-2H-tetrazole-5-carboxamides for photoaffinity labeling of aminergic G-protein coupled receptors

D. Zhukovsky^a, E. V. Kanov^a, R. R. Gainetdinov^a, M. Yu. Krasavin<sup>ab

a</sup> Institute of Chemistry, St. Petersburg State University, St. Petersburg, Russian Federation
^b Immanuel Kant Baltic Federal University, Kaliningrad, Russian Federation

Abstract: A four-step approach to 2-aryl-2H-tetrazole-5-carboxamides bearing GPCR-focused N-substituted piperazine residues involves ‘SAFE’ diazotransfer onto 1-(piperazin-1-yl)butane-1,3-diones followed by [3+2] cycloaddition of arenediazonium cations at the intermediate ααα-diazo acetamides. The compounds prepared are intended for photoaffinity labeling of aminergic G-protein coupled receptors.

Keywords: α-diazo acetamides, [3+2] cycloaddition, silver(t) catalysis, tetrazoles, GPCR privileged ligands, photoaffinity labeling.

Language: English

DOI: 10.1016/j.mencom.2022.09.011

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