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A3-coupling reactions on the synthesis of bioactive nitrogen containing compounds

Grant number: 11/11613-8
Support type:Regular Research Grants
Duration: March 01, 2012 - April 30, 2014
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal researcher:Alcindo Aparecido dos Santos
Grantee:Alcindo Aparecido dos Santos
Home Institution: Instituto de Química (IQ). Universidade de São Paulo (USP). São Paulo , SP, Brazil


This project aims the development and application of tri-component coupling reactionof amines, aldehydes and alkynes (A3) on the synthesis of hidroxy-propargylamines, which will be employed in the synthesis of alkaloids and other nitrogen containingbioactive compounds. A3-coupling reaction is a power tool for the carbon-carbon andcarbon-heteroatom bond formation allowing the preparation of functionalized skeletons of great synthetic utility. The proposal is centered in the coupling of anorganometallic generated in situ from a terminal alkynol and a metal salt or complex, and a nitrogen containing electrophile (imine or iminium salt). In previous investigations we prepared some hydroxy-propargylpiperidones by the A3-couplingreaction of aldehydes, 4-piperidone and alkynols. These compounds were submittedto an enzymatic kinetic resolution study. In this way, here we intend to investigate inthis project the preparation of palladacycle derivatives to evaluate its catalyticactivities; the piperidonic A3-coupling products will be converted into propargylamine derivatives to evaluate their biological activities. The conversion of propargylpiperidones (tertiary amines) in the corresponding primary amines, resulting inhydroxy-propargylamines precursors of cyclic bioactive alkaloids, including doublebond unsaturated ones, which could be prepared by chemoselective triple bondreduction. Procedures involving alternative NH2 source reagents instead of piperidonehydrate and also the asymmetric version of the A3-coupling reaction will beinvestigated. Particularly, we intend to use optically active benzylamines and 2-methyl-2-propanesulfinamide as well catalytic asymmetric ligands. (AU)

Scientific publications (10)
(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)
ARAUJO, JOSE E.; LODEIRO, CARLOS; CAPELO, JOSE L.; RODRIGUEZ-GONZALEZ, BENITO; DOS SANTOS, ALCINDO A.; SANTOS, HUGO M.; FERNANDEZ-LODEIRO, JAVIER. Novel nanocomposites based on a strawberry-like gold- coated magnetite (Fe@Au) for protein separation in multiple myeloma serum samples. NANO RESEARCH, v. 8, n. 4, p. 1189-1198, APR 2015. Web of Science Citations: 17.
RAFAELA C. CARMONA; EDISON P. WENDLER; GEORGE H. SAKAE; JOÃO V. COMASSETO; ALCINDO A. DOS SANTOS. A3-Coupling Reaction as a Strategy Towards the Synthesis of Alkaloids. Journal of the Brazilian Chemical Society, v. 26, n. 1, p. -, Jan. 2015.
CARMONA, RAFAELA C.; WENDLER, EDISON P.; SAKAE, GEORGE H.; COMASSETO, JOAO V.; DOS SANTOS, ALCINDO A. A(3)- Coupling Reaction as a Strategy Towards the Synthesis of Alkaloids. Journal of the Brazilian Chemical Society, v. 26, n. 1, p. 117-123, JAN 2015. Web of Science Citations: 5.
FERNANDEZ-LODEIRO, JAVIER; PINATTO-BOTELHO, MARCOS FELIPE; SOARES-PAULINO, ANTONIO A.; GONCALVES, AUGUSTO CESAR; SOUSA, BRUNO A.; PRINCIVAL, CLEVERSON; DOS SANTOS, ALCINDO A. Synthesis and biological properties of selenium- and tellurium-containing dyes. DYES AND PIGMENTS, v. 110, n. SI, p. 28-48, NOV 2014. Web of Science Citations: 18.
REIS DE SA, LEANDRO FIGUEIRA; TOLEDO, FABIANO TRAVANCA; DE SOUSA, BRUNO ARTUR; GONCALVES, AUGUSTO CESAR; TESSIS, ANA CLAUDIA; WENDLER, EDISON P.; COMASSETO, JOAO V.; DOS SANTOS, ALCINDO A.; FERREIRA-PEREIRA, ANTONIO. Synthetic organotelluride compounds induce the reversal of Pdr5p mediated fluconazole resistance in Saccharomyces cerevisiae. BMC Microbiology, v. 14, JUL 26 2014. Web of Science Citations: 3.
DONATONI, MARIA C.; JUNIOR, GILMAR A. B.; DE OLIVEIRA, KLEBER T.; ANDO, ROMULO A.; BROCKSOM, TIMOTHY J.; DOS SANTOS, ALCINDO A. Solvent-free Diels-Alder reactions catalyzed by FeCl3 on Aerosil((R)) silica. Tetrahedron, v. 70, n. 20, p. 3231-3238, MAY 20 2014. Web of Science Citations: 8.
ZANIN, FABIO G.; MACEDO, ALEXANDRA; ARCHILHA, MARCOS VINICIOS L. R.; WENDLER, EDISON P.; DOS SANTOS, ALCINDO A. A one-pot glycerol-based additive-blended ethyl biodiesel production: A green process. Bioresource Technology, v. 143, p. 126-130, SEP 2013. Web of Science Citations: 12.
CARMONA, RAFAELA C.; SCHEVCIW, EVELYN P.; PETRARCA DE ALBUQUERQUE, JOAO L.; WENDLER, EDISON P.; DOS SANTOS, ALCINDO A. Joint use of microwave and glycerol-zinc (II) acetate catalytic system in the synthesis of 2-pyridyl-2-oxazolines. GREEN PROCESSING AND SYNTHESIS, v. 2, n. 1, SI, p. 35-42, FEB 2013. Web of Science Citations: 9.
EDISON P. WENDLER; ALCINDO A. DOS SANTOS. A general A³: coupling reaction based on functionalized alkynes. Química Nova, v. 36, n. 8, p. -, 2013.
WENDLER, EDISON P.; DOS SANTOS, ALCINDO A. A GENERAL A(3)-COUPLING REACTION BASED ON FUNCTIONALIZED ALKYNES. Química Nova, v. 36, n. 8, p. 1155+, 2013. Web of Science Citations: 2.

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