Applycation of new organometallic reagents in the functionalization of substances of synthetic interest

• Grant number: 13/04766-8
• Support Opportunities: Regular Research Grants
• Start date: July 01, 2013
• End date: June 30, 2015
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Giuliano Cesar Clososki
• Grantee: Giuliano Cesar Clososki
• Host Institution: Faculdade de Ciências Farmacêuticas de Ribeirão Preto (FCFRP). Universidade de São Paulo (USP). Ribeirão Preto , SP, Brazil

Abstract

Magnesium and zinc organometallic reagents complexed with lithium chloride were recently introduced in the literature and have show a great potential in the funcionalization of aromatic and heterocyclic substrates. However, until now, their reactivity with many important substrates was not properly studied. This is the case of aromatic indolizines, quinoxalines, isoquinolines and nitriles that, despite the large field of application in organic synthesis, have not received the necessary attention from the researchers that work in this field. Thus, the main objective of this project is to investigate the application of this modern organometallic reagents in the functionalization of substrates of great synthetic interest. Aiming to demonstrate the synthetic importance of the developed methodologies, we have also planned to apply them in the synthesis or structural modification of bioactive molecules, such as synthetic derivatives of chloroquin, a substance that has been used against malaria. Moreover, all new compounds to be synthesized in this project could be tested by the research groups of the Faculty of Pharmaceutical Sciences of Ribeirão Preto that work on the biological evaluation of natural and synthetic substances. (AU)

Scientific publications

(4)

(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)

VON ZUBEN, L. G.; SCHORKOPF, D. L. P.; ELIAS, L. G.; VAZ, A. L. L.; FAVARIS, A. P.; CLOSOSKI, G. C.; BENTO, J. M. S.; NUNES, T. M.. Interspecific chemical communication in raids of the robber bee Lestrimelitta limao. Insectes Sociaux, v. 63, n. 2, p. 339-347, MAY 2016. (10/10027-5, 13/04766-8, 13/01918-1, 10/04704-4, 11/22991-3)

FERREIRA, SAMUEL R. A.; FRANCO, MARCIA S. F.; DINIZ, EVELYN M. L. P.; EMERY, FLAVIO DA SILVA; CLOSOSKI, GIULIANO CESAR. Drug Likeness and Selective Functionalization of Quinoxalines. CURRENT ORGANIC SYNTHESIS, v. 12, n. 6, p. 714-729, 2015. (12/14362-9, 12/20990-2, 13/04766-8, 12/08589-0)

DOS SANTOS, FERNANDA M.; BATISTA, JOAO H. C.; VESSECCHI, RICARDO; CLOSOSKI, GIULIANO C.. Directed Functionalization of Cyano-Substituted Furans and Thiophenes with TMPMgCl center dot LiCl. Synlett, v. 26, n. 20, p. 2795-2800, DEC 2015. (13/04766-8, 12/13740-0, 14/23604-1)

AMARAL, MONICA F. Z. J.; BAUMGARTNER, AMANDA A.; VESSECCHI, RICARDO; CLOSOSKI, GIULIANO C.. Directed Metalation of 1-Ester-Substituted Indolizines: Base/Electrophile-Controlled Regioselective Functionalization. ORGANIC LETTERS, v. 17, n. 2, p. 238-241, JAN 16 2015. (13/04766-8, 11/20742-6)