Synthesis of 4-Arylselanyl-1 H-1,2,3-triazoles from Selenium-Containing Carbinols

Francesca Begini; Renata A Balaguez; Allya Larroza; Eric F Lopes; Eder João Lenardão; Claudio Santi; Diego Alves

doi:10.3390/molecules26082224

Synthesis of 4-Arylselanyl-1 H-1,2,3-triazoles from Selenium-Containing Carbinols

Molecules. 2021 Apr 12;26(8):2224. doi: 10.3390/molecules26082224.

Authors

Francesca Begini¹, Renata A Balaguez², Allya Larroza², Eric F Lopes², Eder João Lenardão², Claudio Santi¹, Diego Alves²

Affiliations

¹ Group of Catalysis, Synthesis and Organic Green Chemistry, Department of Pharmaceutical Sciences University of Perugia Via del Liceo 1, 06123 Perugia, Italy.
² LASOL-CCQFA, Universidade Federal de Pelotas-UFPel, P.O. Box 354, 96010-900 Pelotas, Brazil.

Abstract

In this work, we present a simple way to achieve 4-arylselanyl-1H-1,2,3-triazoles from selenium-containing carbinols in a one-pot strategy. The selenium-containing carbinols were used as starting materials to produce a range of selanyl-triazoles in moderate to good yields, including a quinoline and Zidovudine derivatives. One-pot protocols are crucial to the current concerns about waste production and solvent consumption, avoiding the isolation and purification steps of the reactive terminal selanylalkynes. We could also isolate an interesting and unprecedented by-product with one alkynylselenium moiety connected to the triazole.

Keywords: 1,2,3-triazoles; carbinols; click chemistry; cycloaddition; heterocycles; selenium.