Synthesis of triazoles from epoxides

• Grant number: 12/22841-4
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• Start date: February 01, 2013
• End date: January 31, 2014
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Andre Luiz Meleiro Porto
• Grantee: Matheus Andrade Meirelles
• Host Institution: Instituto de Química de São Carlos (IQSC). Universidade de São Paulo (USP). São Carlos , SP, Brazil

Abstract

This project is aimed the synthesis of racemic and enantiopure triazoles from epoxides. The synthesis of beta-azido-alcohols is performed by conventional heating and / or microwave irradiation. The synthesis of beta-azido-alcohols and beta-azido-acetates by biocatalysis is obtained via hydrolysis reaction catalyzed by lipase from Candida antarctica (CALB). Initially, it is obtained the corresponding (±)-beta-azido- alcohol by opening the epoxide in aqueous medium in the presence of sodium azide. The (±)-beta-azido-alcohol is esterified with acetic anhydride and pyridine, yielding the (±)-beta-azido-acetate, which is subsequently subjected to enzymatic hydrolysis reaction by CALB. The enantiomerically pure and / or enriched products, after purification by column chromatography, will undergo cyclization to yield the triazoles.(AU)

Scientific publications

(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)

MEIRELLES, MATHEUS A.; JELLER, ALEX H.; FERREIRA, IRLON M.; RAMINELLI, CRISTIANO; FARIA, RAQUEL S.; SILVEIRA-LACERDA, ELISANGELA DE PAULA; PORTO, ANDRE L. M.. BiocatalyticProduction of Chiral Benzotriazoles Employing Conventional Heating and Microwave Radiation. CURRENT MICROWAVE CHEMISTRY, v. 4, n. 3, p. 191-198, 2017. (12/22841-4)