Synthesis of bioactive compounds and studies of relative stereochemistry by hydrogen nuclear magnetic resonance (1H NMR)

• Grant number: 15/00975-7
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• Start date: July 01, 2015
• End date: February 28, 2017
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Agreement: Coordination of Improvement of Higher Education Personnel (CAPES)
• Principal Investigator: Fernando Antonio Santos Coelho
• Grantee: Rodrigo Antonio Cormanich
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil

Abstract

In this research project we propose the study of highly functionalized 5,6,7,8-tetrahydroindolizines and fluorinated thymol and carvacrol derivatives. The tetrahydroindolizines will be synthesized using Morita-Hillman adducts as substrates for heterogeneous hydrogenation reactions. The stereoselectivity of the hydrogenation reactions will be determined using 1H NMR parameters, such as, indirect coupling constants H-H to three bonds (3JHH) and nuclear overhauser effect (NOE). The fluorinated derivatives of thymol and carvacrol will be synthesized through a direct fluorination in different positions of the aromatic ring. The formation of diazonium salts followed by the treament with a fluorination agent will be the method of choice. Studies of the physico-chemical properties of these fluorinated derivatives will be carry out. These studies could reveal new properties for these compounds which could interest medicinal chemistry and agrochemical areas. NMR (1H and 19F) as well as theoretical calculations (DFT and/or ab initio) will be used as tools for the comprehension of these properties. (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)

CORR, MICHAEL J.; CORMANICH, RODRIGO A.; VON HAHMANN, CORTNEY N.; BUEHL, MICHAEL; CORDES, DAVID B.; SLAWIN, ALEXANDRA M. Z.; O'HAGAN, DAVID. Fluorine in fragrances: exploring the difluoromethylene (CF2) group as a conformational constraint in macrocyclic musk lactones. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 14, n. 1, p. 211-219, 2016. (15/00975-7)

ZEOLY, LUCAS A.; ACCONCIA, LAIS V.; RODRIGUES JR, MANOEL T.; SANTOS, HUGO; CORMANICH, RODRIGO A.; PANIAGUA, JUAN C.; MOYANO, ALBERT; COELHO, FERNANDO. One-pot organocatalyzed synthesis of tricyclic indolizines. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 21, n. 17, p. 15-pg., 2023-04-14. (13/07600-3, 14/26027-5, 13/24386-5, 18/02611-0, 15/00975-7, 15/09205-0)