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Application of Isoxazolones in Organic Synthesis

Grant number: 17/24017-0
Support type:Regular Research Grants
Duration: February 01, 2018 - January 31, 2020
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal Investigator:Igor Dias Jurberg
Grantee:Igor Dias Jurberg
Home Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil


This project aims to study a series of transformations involving isoxazol-5-ones within the context of organocatalysis, as well as metal catalysis. Specifically, the following transformations will be studied: organocatalyzed 1,2-additions to 4-substituted isoxazol-5-ones aiming at the preparationof beta-aminoacid derivatives, the use of dienamines derived from alkylidene isoxazolones and pyrazolones aiming at their functionalization and the development of cascade reactions, the decarboxylation of isoxazolones and their trapping with nucleophiles, the preparation of functionalized indoles, pyridines, isoxazoles and the generation of benzyne and their further transformations. All these projects have the goal of extending the chemistry of isoxazol-5-ones, in order to demonstrate their versatility in organic synthesis. As a consequence, we aim to establish this class of compounds as a powerful source for a variety of functional groups and reactivity patterns that can be accessed, thus contributing to the development of new catalytic technologies. (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)
OKADA JR, CELSO Y.; DOS SANTOS, CAIO Y.; JURBERG, IGOR D. Blue light-promoted N-H insertion of amides, isatins, sulfonamides and imides into aryldiazoacetates: Synthesis of unnatural alpha-aryl amino acid derivatives. Tetrahedron, v. 76, n. 51, SI DEC 18 2020. Web of Science Citations: 2.
DA SILVA, AMANDA F.; LEONARCZYK, IVES A.; FERREIRA, MARCO A. B.; JURBERG, IGOR D. Diastereodivergent aminocatalyzed spirocyclization strategies using 4-alkylideneisoxazol-5-ones and methyl vinyl ketones. ORGANIC CHEMISTRY FRONTIERS, v. 7, n. 22, p. 3599-3607, NOV 21 2020. Web of Science Citations: 0.
SIGRIST, RENATA; LUHAVAYA, HANNA; MCKINNIE, SHAUN M. K.; DA SILVA, AMANDA FERREIRA; JURBERG, IGOR D.; MOORE, BRADLEY S.; DE OLIVEIRA, LUCIANA GONZAGA. Nonlinear Biosynthetic Assembly of Alpiniamide by a Hybrid cis/trans-AT PKS-NRPS. ACS Chemical Biology, v. 15, n. 4, p. 1067-1077, APR 17 2020. Web of Science Citations: 0.
DA SILVA, AMANDA F.; AFONSO, MARCO A. S.; CORMANICH, RODRIGO A.; JURBERG, IGOR D. Room Temperature Coupling of Aryldiazoacetates with Boronic Acids Enhanced by Blue Light Irradiation. CHEMISTRY-A EUROPEAN JOURNAL, v. 26, n. 25 MAR 2020. Web of Science Citations: 0.
QUEVEDO-ACOSTA, YOVANNY; JURBERG, IGOR D.; GAMBA-SANCHEZ, DIEGO. Activating Imides with Triflic Acid: A General Intramolecular Aldol Condensation Strategy Toward Indolizidine, Quinolizidine, and Valmerin Alkaloids. ORGANIC LETTERS, v. 22, n. 1, p. 239-243, JAN 3 2020. Web of Science Citations: 5.
STIVANIN, MATEUS L.; FERNANDES, ALESSANDRA A. G.; DA SILVA, AMANDA F.; OKADA JR, CELSO Y.; JURBERG, IGOR D. Blue Light-Promoted N-H Insertion of Carbazoles, Pyrazoles and 1,2,3-Triazoles into Aryldiazoacetates. ADVANCED SYNTHESIS & CATALYSIS, v. 362, n. 5 JAN 2020. Web of Science Citations: 12.
THUROW, SAMUEL; FERNANDES, ALESSANDRA A. G.; QUEVEDO-ACOSTA, YOVANNY; DE OLIVEIRA, MATHEUS F.; DE OLIVEIRA, MARCELO G.; JURBERG, IGOR D. Preparation of Organic Nitrates from Aryldiazoacetates and Fe(NO3)(3)center dot 9H(2)O. ORGANIC LETTERS, v. 21, n. 17, p. 6909-6913, SEP 6 2019. Web of Science Citations: 1.
FERNANDES, ALESSANDRA A. G.; DA SILVA, AMANDA F.; OKADA, JR., CELSO Y.; SUZUKAWA, VITOR; CORMANICH, RODRIGO A.; JURBERG, IGOR D. General Platform for the Conversion of Isoxazol-5-ones to 3,5-Disubstituted Isoxazoles via Nucleophilic Substitutions and Palladium Catalyzed Cross-Coupling Strategies. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2019, n. 19, p. 3022-3034, MAY 26 2019. Web of Science Citations: 0.
FERNANDES, ALESSANDRA A. G.; STIVANIN, MATEUS L.; JURBERG, IGOR D. RuCl3/PPh3 - Catalyzed Direct Conversion of Isoxazol-5-ones to 2,3-Disubstituted Pyridines. CHEMISTRYSELECT, v. 4, n. 12, p. 3360-3365, MAR 29 2019. Web of Science Citations: 2.
BERTUZZI, DIEGO L.; BECHER, TIAGO B.; CAPRETI, NAYLIL M. R.; AMORIM, JULIO; JURBERG, IGOR D.; MEGIATTO, JR., JACKSON D.; ORNELAS, CATIA. General Protocol to Obtain D-Glucosamine from Biomass Residues: Shrimp Shells, Cicada Sloughs and Cockroaches. GLOBAL CHALLENGES, v. 2, n. 11 NOV 2018. Web of Science Citations: 0.
DA SILVA, AMANDA F.; FERNANDES, ALESSANDRA A. G.; THUROW, SAMUEL; STIVANIN, MATEUS L.; JURBERG, IGOR D. Isoxazol-5-ones as Strategic Building Blocks in Organic Synthesis. SYNTHESIS-STUTTGART, v. 50, n. 13, p. 2473-2489, JUL 2018. Web of Science Citations: 11.

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