Synthesis of 3-indolyltriazoles via Sonogashira coupling and azide-alkyne cycloaddition promoted by supported copper nanoparticles
| Autor: | Stabile, S., Vitale, C. A., Rodríguez-Franco, María Isabel |
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| Přispěvatelé: | Comunidad de Madrid, European Commission, Ministerio de Economía y Competitividad (España), Universidad Nacional del Sur, Ministerio de Ciencia, Innovación y Universidades (España) |
| Rok vydání: | 2019 |
| Předmět: | |
| Zdroj: | Digital.CSIC. Repositorio Institucional del CSIC instname |
| Popis: | 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 N-protected 3-iodoindoles were subjected to a Sonogashira cross-coupling reaction with trimethylsilylacetylene 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 cycloaddition catalysed by copper nanoparticles (CuNPs) immobilized on activated carbon, which were prepared using the CuCl2-Li-4,4¿-Di-tert-butylbiphenyl (DTBB) reducing system previously reported by our group [2]. This work was performed in the Instituto de Química Médica (IQM-CSIC) with grants from the following agencies: Dirección General de Investigación e Innovación de la Comunidad de Madrid y Fondo Europeo de Desarrollo Regional (B2017/BMD-3827); Ministerio de Ciencia, Innovación y Universidades, Agencia Estatal de Investigación y FEDER (SAF2015-64948-C2-1-R and RTI2018-093955-B-C21); Universidad Nacional del Sur, programa de Pasantías en Centros de Investigación destinada a Jóvenes Docentes. |
| Databáze: | OpenAIRE |
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