SYNTHESIS OF 3-INDOLYLTRIAZOLES VIA SONOGASHIRA COUPLING AND AZIDE-ALKYNE CYCLOADDITION PROMOTED BY SUPPORTED COPPER NANOPARTICLES

VITALE, CRISTIAN ALEJANDRO; RODRÍGUEZ-FRANCO, MA. ISABEL; STABILE, SANTIAGO ARMANDO

Madrid

Simposio; 6TH YOUNG RESEARCHERS SYMPOSIUM; 2019

Sociedad Española de Quimica Terapeutica

In this work we present the synthesis of a novel series of 3-indolyl-1,4-disubstituted 1,2,3-triazoles. The key steps in the synthetic route are shown in Scheme 1. A series of Nprotected3-iodoindoles were subjected to a Sonogashira cross-coupling reaction withtrimethylsilylacetylene in presence of PdCl2(PPh)3 and CuI as catalysts and TEA as base,following the procedures described by Boger [1]. After deprotection of the silyl group, 1,2,3-triazoles were obtained through the azide-alkyne Huisgen 1,3-dipolar cycloadditioncatalysed by copper nanoparticles (CuNPs) immobilized on activated carbon, which wereprepared using the CuCl2-Li-4,4ʹ-Di-tert-butylbiphenyl (DTBB) reducing system previouslyreported by our group.