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Flow modified Lehmstedt-Tanasescu reactions for the scaled production of medicinally important heterocyclic building blocks

Grant number: 19/05838-9
Support type:Scholarships abroad - Research Internship - Doctorate
Effective date (Start): May 31, 2019
Effective date (End): October 30, 2019
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal researcher:Giuliano Cesar Clososki
Grantee:Valter Eduardo Murie
Supervisor abroad: Ian Baxendale
Home Institution: Faculdade de Ciências Farmacêuticas de Ribeirão Preto (FCFRP). Universidade de São Paulo (USP). Ribeirão Preto , SP, Brazil
Research place: Durham University (DU), England  
Associated to the scholarship:15/21364-6 - Applicantion of Organometallic Reagents in the Directed Functionalization of Quinolines Aimming the Synthesis of Medicinal Interest Compounds, BP.DR


Flow chemistry has been employed as new synthetic tool in order to optimize reaction conditions, improve the atom economy, allow to handle hazardous reagents, promote safety process and to support scale-up. A number of classical reactions have been performed under flow conditions in good yields and some synthetic challenges have already been solved. However, the formation of solids and precipitates in flow reactors require specific processing solution and represent an area to be developed. In this context, Lehmstedt-Tanasescu reaction has not been explored under flow conditions and the formations of a slurry that makes stirring difficult under batch conditions is a challenging point. Therefore, this project envisages the investigation of Lehmestedt-Tanasescu reaction under continuous flow process in order to prepare 2,1-benzisoxazoles and acridones. (AU)

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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)
MURIE, VALTER E.; NICOLINO, V, PAULA; DOS SANTOS, THIAGO; GAMBACORTA, GUIDO; NISHIMURA, V, RODOLFO H.; PEROVANI, ICARO S.; FURTADO, LUCIANA C.; COSTA-LOTUFO, V, LETICIA; DE OLIVEIRA, ANDERSON MORAES; VESSECCHI, RICARDO; BAXENDALE, IAN R.; CLOSOSKI, GIULIANO C. Synthesis of 7-Chloroquinoline Derivatives Using Mixed Lithium-Magnesium Reagents. Journal of Organic Chemistry, v. 86, n. 19, p. 13402-13419, OCT 1 2021. Web of Science Citations: 0.
DARTAGNAN S. P. FERREIRA; VALTER E. MURIE; THIAGO DOS SANTOS; PAULO C. VIEIRA; GIULIANO C. CLOSOSKI. Recentes avanços na funcionalização seletiva de quinolinas. Química Nova, v. 44, n. 5, p. 599-615, 2021.

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