Directed functionalization of aromatic indolizines aiming to obtain bioactive substances

• Grant number: 15/03007-1
• Support Opportunities: Scholarships in Brazil - Doctorate (Direct)
• Effective date (Start): June 01, 2015
• Effective date (End): November 30, 2019
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Giuliano Cesar Clososki
• Grantee: Camila Rodrigues de Souza Bertallo
• Host Institution: Faculdade de Ciências Farmacêuticas de Ribeirão Preto (FCFRP). Universidade de São Paulo (USP). Ribeirão Preto , SP, Brazil
• Associated scholarship(s): 18/02855-7 - Iridium-catalyzed C-H activation/borylation of aromatic indolizines, BE.EP.DD

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, 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 objective of this project is to conduct a comprehensive study on the application of organometallic reagents in the regioselective metalation of functionalized indolizines. In this sense, it is intended to prepare substrates with different functional groups and at different positions of the indolizínic ring. The reaction of organometallic intermediates obtained from these substrates with different electrophiles could lead to synthesis of highly functionalized derivatives, with great potential for application in organic synthesis. In addition, by employing techniques of remote metalation aromatic directed ("DREM"), is also to synthesize complex structure of indolizines, that would not be easily accessed by conventional methods. Finally, to complement the synthetic study and aiming to demonstrate the feasibility of the developed methodologies, that present the best results will also be subjected to optimization protocols in continuous flow. (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)

BERTALLO, CAMILA R. S.; BERLIM, LEONARDO S.; OLIVIER, DANILO S.; ARROIO, THAIS R.; ITO, AMANDO S.; CLOSOSKI, GIULIANO C.. Synthesis and photophysical properties of 2-aryl-5-carbonyl indolizines. DYES AND PIGMENTS, v. 198, FEB 2022. (18/14150-8, 15/03007-1, 18/02855-7, 20/13962-9)

Academic Publications

(References retrieved automatically from State of São Paulo Research Institutions)

BERTALLO, Camila Rodrigues de Souza. Development of a comprehensive study on base-controlled regioselective functionalization and Iridium-Catalysed Borylation of indolizines. 2020. Doctoral Thesis - Universidade de São Paulo (USP). Faculdade de Ciências Farmacêuticas de Ribeirão Preto (PCARP/BC) Ribeirão Preto.