Synthesis of new heterocycles exhibiting potential biological activities by exploring the Morita-Baylis-Hillman adducts as building blocks

• Grant number: 16/23005-6
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• Start date: March 01, 2017
• End date: January 31, 2020
• 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: Fábio de Souza Fernandes
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil

Abstract

This research project aims to further explore the synthetic potentiality of Morita-Baylis-Hillman adducts as versatile building blocks for the preparation of heterocycles with new structural patterns and potential biological activities. Reactions of N-alkylation and reductive amination in alpha-amino-esters, prepared in a three-step sequence from MBH adducts, will be used as strategy for the synthesis of new heterocycles derived from 2-piperazinones, 2-morpholinones and 2-quinolones. The biological profile of these new heterocycles will be evaluated. In a second subproject, we intend to explore the C-N coupling reactions on the same alpha-amino-esters to obtain substituted indolines with good stereoselectivity. (AU)

Scientific publications

(5)

(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)

FERNANDES, FABIO S.; RODRIGUES, JR., MANOEL T.; ZEOLY, LUCAS A.; CONTI, CAROLINE; ANGOLINI, CELIO F. F.; EBERLIN, MARCOS NOGUEIRA; COELHO, FERNANDO. Vinyl-1,2,4-oxadiazoles Behave as Nucleophilic Partners in Morita-Baylis-Hillman Reactions. Journal of Organic Chemistry, v. 83, n. 24, p. 15118-15127, DEC 21 2018. (18/02611-0, 13/07600-3, 16/23005-6)

SILVA, THIAGO S.; RODRIGUES, JR., MANOEL T.; SANTOS, HUGO; ZEOLY, LUCAS A.; ALMEIDA, WANDA P.; BARCELOS, ROSIMEIRE C.; GOMES, RALPH C.; FERNANDES, FABIO S.; COELHO, FERNANDO. Recent advances in indoline synthesis. Tetrahedron, v. 75, n. 14, p. 2063-2097, APR 5 2019. (15/09205-0, 18/02611-0, 13/07600-3, 16/23005-6)

CAPRETZ-AGY, ANDRE; FERNANDES, FABIO S.; RODRIGUES JR, MANOEL T.; CONTI, CAROLINE; COELHO, FERNANDO. Aza-Morita-Baylis-Hillman Reaction with Vinyl-oxadiazoles: An Expeditious Approach to Access New Heterocyclic Arrangements. Synlett, v. 31, n. 6, p. 622-626, APR 1 2020. (18/02611-0, 13/07600-3, 16/23005-6)

FERNANDES, FABIO S.; SANTOS, HUGO; LIMA, SAMIA R.; CONTI, CAROLINE; RODRIGUES JR, MANOEL T.; ZEOLY, LUCAS A.; FERREIRA, LEONARDO L. G.; KROGH, RENATA; ANDRICOPULO, ADRIANO D.; COELHO, FERNANDO. Discovery of highly potent and selective antiparasitic new oxadiazole and hydroxy-oxindole small molecule hybrids. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, v. 201, SEP 1 2020. (18/02611-0, 13/07600-3, 16/23005-6, 15/09205-0)

CAMILO, NILTON S.; SANTOS, HUGO; ZEOLY, LUCAS A.; FERNANDES, FABIO S.; RODRIGUES JR, MANOEL T.; SILVA, THIAGO S.; LIMA, SAMIA R.; SERAFIM, JOSE CLAUDIO; DE OLIVEIRA, ALINE S. B.; CARPANEZ, ARTHUR G.; et al. An Improved Protocol for the Morita-Baylis-Hillman Reaction Allows Unprecedented Broad Synthetic Scope. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. N/A, p. 9-pg., 2022-01-19. (18/00299-0, 18/02611-0, 16/23005-6, 13/07600-3, 15/09205-0)