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Carbonylative coupling and intramolecular cycloaddition [2 + 2] reactions employing D-Glucal

Grant number: 17/24821-4
Support type:Regular Research Grants
Duration: March 01, 2018 - February 29, 2020
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal Investigator:Helio Alexandre Stefani
Grantee:Helio Alexandre Stefani
Home Institution: Faculdade de Ciências Farmacêuticas (FCF). Universidade de São Paulo (USP). São Paulo , SP, Brazil

Abstract

The main focus of the project is the use of 3,4,6-tri-O-acetyl-D-glucal for use in transformations involving carbonyl coupling reactions (Sonogashira, Suzuki-Miyaura and Stille), selenosugars, and intermolecular [2+2] cycloaddition. It is also intended to evaluate the biological activity of the compounds prepared (e.g. antifungal, anticancer and anti-inflammatory activity). (AU)

Scientific publications (12)
(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)
COSTA, CLAUDIA A.; LOPES, RAYSSA M.; FERRAZ, LETICIA S.; ESTEVES, GABRIELA N. N.; DI IORIO, JULIANA F.; SOUZA, ALINE A.; DE OLIVEIRA, ISADORA M.; MANARIN, FLAVIA; JUDICE, WAGNER A. S.; STEFANI, HELIO A.; RODRIGUES, TIAGO. Cytotoxicity of 4-substituted quinoline derivatives: Anticancer and antileishmanial potential. Bioorganic & Medicinal Chemistry, v. 28, n. 11 JUN 1 2020. Web of Science Citations: 0.
SOARES-PAULINO, ANTONIO AUGUSTO; STEFANI, HELIO A. . EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, JUN 2020. Web of Science Citations: 0.
DE OLIVEIRA, ISADORA M.; ESTEVES, HENRIQUE A.; DARBEM, MARIANA P.; SARTORELLI, ARTHUR; CORRERA, THIAGO C.; RODRIGUES-OLIVEIRA, ANDRE F.; PIMENTA, DANIEL C.; ZUKERMAN-SCHPECTOR, JULIO; MANARIN, FLAVIA; STEFANI, HELIO A. Stereo- and Regioselective Cu-Catalyzed Hydroboration of Alkynyl Chalcogenoethers. CHEMCATCHEM, MAY 2020. Web of Science Citations: 0.
ESTEVES, HENRIQUE A.; DARBEM, MARIANA P.; PIMENTA, DANIEL C.; STEFANI, HELIO A. Carbonylative Negishi-Type Coupling of 2-Iodoglycals with Alkyl and Aryl Halides. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2019, n. 44, p. 7384-7388, NOV 30 2019. Web of Science Citations: 1.
DARBEM, MARIANA P.; ESTEVES, HENRIQUE A.; DE OLIVEIRA, ISADORA M.; PIMENTA, DANIEL C.; STEFANI, HELIO A. Palladium-Catalyzed Thio- and Selenocarbonylation of 2-Iodoglycals. CHEMCATCHEM, v. 12, n. 2 NOV 2019. Web of Science Citations: 0.
DE OLIVEIRA, ISADORA M.; ESTEVES, C. HENRIQUE A.; DARBEM, MARIANA P.; PIMENTA, DANIEL C.; ZUKERMAN-SCHPECTOR, JULIO; FERREIRA, ANTONIO G.; STEFANI, HELIO A.; MANARIN, FLAVIA. Iron (III)-Promoted Synthesis of Substituted 4H-Chalcogenochromenes and Chemoselective Functionalization. ADVANCED SYNTHESIS & CATALYSIS, v. 361, n. 13, p. 3163-3172, JUL 2 2019. Web of Science Citations: 1.
SANTOS, FABIANO S.; ZANOTTO, GABRIEL M.; ARGOMEDO, LUIS M. Z.; DARBEM, MARIANA P.; GONCALVES, PAULO F. B.; STEFANI, HELIO A.; RODEMBUSCH, FABIANO S. Synthesis, experimental and theoretical photophysical study of proton transfer based oxazoline fluorophores. Potential tailor made optical sensors for enantiomeric detection in solution. DYES AND PIGMENTS, v. 165, p. 372-382, JUN 2019. Web of Science Citations: 0.
VASCONCELOS, STANLEY N. S.; REIS, JOEL S.; DE OLIVEIRA, ISADORA M.; BALFOUR, MICHAEL N.; STEFANI, HELIO A. Synthesis of symmetrical biaryl compounds by homocoupling reaction. Tetrahedron, v. 75, n. 13, p. 1865-1959, MAR 29 2019. Web of Science Citations: 5.
BALFOUR, MICHAEL N.; ZUKERMAN-SCHPECTOR, JULIO; DAVILA RODRIGUEZ, MARIA JOSE; REIS, JOEL SAVI; ESTEVES, CARLOS HENRIQUE A.; STEFANI, HELIO A. Combination of Sonogashira coupling and 5-endo-dig cyclization for the synthesis of 2,6-disubstituted-5-azaindoles. Synthetic Communications, v. 49, n. 3, p. 351-358, FEB 1 2019. Web of Science Citations: 0.
DARBEM, MARIANA P.; KANNO, KARINA S.; DE OLIVEIRA, ISADORA M.; ESTEVES, C. HENRIQUE A.; PIMENTA, DANIEL C.; STEFANI, HELIO A. Synthesis of amidoglucals and glucal esters via carbonylative coupling reactions of 2-iodoglucal using Mo(CO)(6) as a CO source. NEW JOURNAL OF CHEMISTRY, v. 43, n. 2, p. 696-699, JAN 14 2019. Web of Science Citations: 6.
DARBEM, MARIANA P.; ESTEVES, C. HENRIQUE A.; DE OLIVEIRA, ISADORA M.; REIS, JOEL S.; PIMENTA, DANIEL C.; STEFANI, HELIO A. Synthesis of d-glyco-alkynone derivatives via carbonylative Sonogashira reaction. RSC ADVANCES, v. 9, n. 17, p. 9468-9474, 2019. Web of Science Citations: 2.
REIS, JOEL S.; FERNANDES, ARTHUR B.; FREITAS-DORR, BARBARA C.; BASTOS, ERICK L.; STEFANI, HELIO A. Oxazoline as acceptor moiety for excited-state intramolecular proton transfer. Tetrahedron, v. 74, n. 48, p. 6866-6872, NOV 29 2018. Web of Science Citations: 2.

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