Combination of organocatalytic and multicomponent reactions in the assymetric synthesis of substituted tetrahydroquinolines

• Grant number: 16/14560-6
• Support type: Scholarships in Brazil - Master
• Effective date (Start): March 01, 2017
• Effective date (End): February 28, 2018
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Cooperation agreement: Coordination of Improvement of Higher Education Personnel (CAPES)
• Principal researcher: Márcio Weber Paixão
• Grantee: Vitor Alcantara Fernandes da Silva
• Home Institution: Centro de Ciências Exatas e de Tecnologia (CCET). Universidade Federal de São Carlos (UFSCAR). São Carlos , SP, Brazil

Abstract

The tetrahydroquinolines are structural components commonly found in natural products. These structures have great importance in the area of medicinal chemistry, because several compounds of this class have some type of biological activity. Due to this importance, there is great interest in the study of new methodologies for synthesis of tetrahydroquinolines to obtain new derivatives whose properties are more efficient for their applications as pharmaceuticals.Having this background in mind, this work has as main objective the development of an innovative and efficient method for the synthesis of 1,2,3,4-tetrahydroquinolines with high structural diversity and potential use as biological systems inhibitors.At first, the research project proposes the synthesis of 1,2,3,4-tetrahydroquinolines by combining, sequentially and one-pot, a organocatalytic Michael reaction and a multicomponent reaction (Ugi-Smiles-3 type components-4-centers). In this way, we can get a wide variety of compounds with a high degree of structural diversity in one-pot fashion. The organocatalytic step is an innovative proposal, not described in the literature, so it should be used to search for optimization of optimal reaction conditions.In order to understand better the mechanism of the reaction, kinetic and computational studies will be conducted to the refinement of the properties of the methodology. Still, it is intended, after synthesis of a wide variety of compounds to test the biological activity of these derivatives. (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)

DA SILVA, VITOR A. F.; DA SILVA, GUSTAVO P.; MATSUO, BIANCA T.; ALI, AKBAR; DAVIS, REBECCA L.; ZUKERMAN-SCHPECTOR, JULIO; CORREA, ARLENE G.; PAIXAO, MARCIO W. Synthesis of (Z)-beta-halo alpha,beta-unsaturated carbonyl systems via the combination of halotrimethylsilane and tetrafluoroboric acid. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 17, n. 3, p. 519-526, JAN 21 2019. Web of Science Citations: 4.