Síntese e caracterização de 1,2,3-triazol derivado da cumarina

• Autor(a) principal: Araújo, Guilherme
• Data de Publicação: 2023
• Idioma: por
• Título da fonte: Manancial - Repositório Digital da UFSM
• dARK ID: ark:/26339/0013000018g4q
• Texto Completo: http://repositorio.ufsm.br/handle/1/30054
• topic: Síntese orgânica; Triazóis; Cicloadição; Cobre; Catálise; CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA

In this work, a methodology was developed for the synthesis of a compound derived from coumarin containing the heterocycle 1,2,3-triazole functionalized with an organoselenium moiety. The method is based on the 1,3-dipolar cycloaddition reaction between 4-(prop-2-yn-1-yloxy)-2H-chromen-2-one 1 and (azidomethyl)(phenyl)selenide 2 to form 4-((1-((phenylselenyl)methyl)-1H-1,2,3- triazol-4-yl)methoxy)-2H-chromen-2-one 3. For this, copper sulfate was used as a catalyst in the presence of sodium ascorbate as reducing agent in a mixture of DMSO and water as solvents. After analyzing the experimental results, it was verified that the ideal reaction conditions to promote the 1,3-dipolar cycloaddition consist in the use of 1 (0.25 mmol), 2 (1 equiv) in the presence of 10 mol% of CuSO4. 5H2O together with 20 mol% sodium ascorbate in 4 mL of the 1:1 mixture of H2O and DMSO. The reaction is performed at room temperature over a period of 16 hours and gives the desired product in a 76% yield. The obtained compound was structurally characterized by 1H and 13C nuclear magnetic resonance (NMR) techniques.