Development and Mechanism Studies of New Synthetic Methodologies for the Synthesis of Bioactive Compounds.

• Grant number: 15/17141-1
• Support Opportunities: Regular Research Grants
• Start date: November 01, 2015
• End date: October 31, 2017
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Ricardo Samuel Schwab
• Grantee: Ricardo Samuel Schwab
• Host Institution: Centro de Ciências Exatas e de Tecnologia (CCET). Universidade Federal de São Carlos (UFSCAR). São Carlos , SP, Brazil

Abstract

Brazil has the basic chemical industry ranked among the world's largest and, at the moment, is choosing to develop its fine chemicals industry. The creation of a solid background for Fine Chemicals will require a change in behavior, once this sector is extremely competitive. In this context, the domain of organic synthesis is an indispensable condition since it allows the development of alternative processes in order to obtain substances with high added value, such as, active pharmaceutical compounds. In fact, the search for more economical technologies through the design and development of short synthetic routes, avoiding the use of anhydrous solvents, inert and reactive systems difficult to handle, and excessive purifications, is of huge importance nowadays. These questions have prompted the research of many scientists, especially in pharmaceutical industry, where is important to synthesize the active substances with a low price and a short time. The requirements listed above can be easily achieved through the use of catalysis and others convergent methodologies. These strategies are of huge interest for both segments of academia and industry. In this project, we wish to develop new methodologies by merging an organocatalyzed reaction with a multicomponent protocol as well as MCR with photochemistry for the synthesis of nitrogen containing heterocycles. The catalytic process will be deeply study by theoretical and practical experiments. Furthermore, all synthesized compounds should have the biological activity explored. (AU)

Scientific publications

(43)

(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)

ROGER GONÇALVES; ERNESTO C. PEREIRA. Chemometric Evaluation of Poly(3-hexylthiophene) Electrochemical Aging Path as a Function of Electrochemical Synthesis Variables. Journal of the Brazilian Chemical Society, v. 33, n. 7, p. 762-771, 2022-06-17. (17/06536-0, 17/11986-5, 11/10897-2, 14/50249-8, 15/17141-1)

KISUKURI, CAMILA M.; FERNANDES, VITOR A.; DELGADO, JOSE A. C.; HAERING, ANDREAS P.; PAIXAO, MARCIO W.; WALDVOGEL, SIEGFRIED R.. Electrochemical Installation of CFH2-, CF2H-, CF3-, and Perfluoroalkyl Groups into Small Organic Molecules. CHEMICAL RECORD, JUN 2021. (19/01973-9, 18/12986-1, 15/17141-1, 14/50249-8)

GONCALVES, ROGER; LIMA, THIAGO M.; PAIXAO, MARCIO W.; PEREIRA, ERNESTO C.. Pristine carbon nitride as active material for high-performance metal-free supercapacitors: simple, easy and cheap. RSC ADVANCES, v. 8, n. 61, p. 35327-35336, 2018. (14/50249-8, 17/06536-0, 15/17141-1, 13/07296-2, 11/10897-2)

SARAIVA, MAIARA T.; COSTA, GABRIEL P.; SEUS, NATALIA; SCHUMACHER, RICARDO F.; PERIN, GELSON; PAIXAO, MARCIO W.; LUQUE, RAFAEL; ALVES, DIEGO. Room-Temperature Organocatalytic Cycloaddition of Azides with beta-Keto Sulfones: Toward Sulfonyl-1,2,3-triazoles. ORGANIC LETTERS, v. 17, n. 24, p. 6206-6209, DEC 18 2015. (15/17141-1, 14/50249-8)

SAVEGNAGO, LUCIELLI; DO SACRAMENTO, MANOELA; BROD, LUCIMAR M. P.; FRONZA, MARIANA G.; SEUS, NATALIA; LENARDAO, EDER J.; PAIXAO, MARCIO W.; ALVES, DIEGO. Phenylselanyl-1H-1,2,3-triazole-4-carbonitriles: synthesis, antioxidant properties and use as precursors to highly functionalized tetrazoles. RSC ADVANCES, v. 6, n. 10, p. 8021-8031, 2016. (15/17141-1, 14/50249-8)

SILVA, SANDRINA; MATSUO, BIANCA T.; DA SILVA, RODRIGO C.; POZZI, LUCAS V.; CORREA, ARLENE G.; ROLLIN, PATRICK; ZUKERMAN-SCHPECTOR, JULIO; FERREIRA, MARCO A. B.; PAIXAO, MARCIO W.. Organocatalyzed Asymmetric Vinylogous Addition of Oxazole-2(3H)-thiones to alpha,beta-Unsaturated Ketones: An Additive-Free Approach for Diversification of Heterocyclic Scaffold. Journal of Organic Chemistry, v. 83, n. 4, p. 1701-1716, FEB 16 2018. (14/50249-8, 12/04986-5, 15/08541-6, 15/17141-1)

JORGE, ERLEN Y. C.; LIMA, THIAGO DE M.; LIMA, CAROLINA G. S.; MARCHINI, LUCAS; CASTELBLANCO, WILLIAM N.; RIVERA, DANIEL G.; URQUIETA-GONZALEZ, ERNESTO A.; VARMA, RAJENDER S.; PAIXAO, MARCIO W.. Metal-exchanged magnetic beta-zeolites: valorization of lignocellulosic biomass-derived compounds to platform chemicals. GREEN CHEMISTRY, v. 19, n. 16, p. 3856-3868, AUG 21 2017. (15/17141-1, 14/50249-8)

XAVIER, DAIANE M.; GOLDANI, BRUNA S.; SEUS, NATALIA; JACOB, RAQUEL G.; BARCELLOS, THIAGO; PAIXAO, MARCIO W.; LUQUE, RAFAEL; ALVES, DIEGO. Sonochemistry in organocatalytic enamine-azide [3+2] cycloadditions: A rapid alternative for the synthesis of 1,2,3-triazoyl carboxamides. ULTRASONICS SONOCHEMISTRY, v. 34, p. 107-114, JAN 2017. (15/17141-1, 14/50249-8)

DE LA TORRE, ALEXANDER F.; RIVERA, DANIEL G.; CONCEPCION, ODETTE; ECHEMENDIA, RADELL; CORREA, ARLENE G.; PAIXAO, MARCIO W.. Multicomponent Synthesis of Cyclic Depsipeptide Mimics by Ugi Reaction Including Cyclic Hemiacetals Derived from Asymmetric Organocatalysis. Journal of Organic Chemistry, v. 81, n. 3, p. 803-809, FEB 5 2016. (15/17141-1, 14/50249-8)

ECHEMENDIA, RADELL; DA SILVA, GUSTAVO P.; KAWAMURA, MEIRE Y.; DE LA TORRE, ALEXANDER F.; CORREA, ARLENE G.; FERREIRA, MARCO A. B.; RIVERA, DANIEL G.; PAIXAO, MARCIO W.. A stereoselective sequential organocascade and multicomponent approach for the preparation of tetrahydropyridines and chimeric derivatives. CHEMICAL COMMUNICATIONS, v. 55, n. 3, p. 286-289, JAN 11 2019. (15/17141-1, 14/50249-8, 17/01754-0, 15/08541-6, 16/12622-4)

MONTEIRO, JULIA L.; MOREIRA, NATALIA M.; DOS SANTOS, DEBORAH A.; PAIXAO, MARCIO W.; CORREA, ARLENE G.. Step economy strategy for the synthesis of amphoteric aminoaldehydes, key intermediates for reduced hydantoins. Pure and Applied Chemistry, v. 90, n. 1, p. 121-132, JAN 2018. (12/07284-1, 15/17141-1, 14/50249-8, 13/07600-3)

KISUKURI, CAMILA M.; FERNANDES, VITOR A.; DELGADO, JOSE A. C.; HAERING, ANDREAS P.; PAIXAO, MARCIO W.; WALDVOGEL, SIEGFRIED R.. Electrochemical Installation of CFH2-, CF2H-, CF3-, and Perfluoroalkyl Groups into Small Organic Molecules. CHEMICAL RECORD, v. 21, n. 9, SI, p. 2502-2525, SEP 2021. (18/12986-1, 15/17141-1, 14/50249-8, 19/01973-9)

MATSUO, BIANCA T.; CORREIA, JOSE TIAGO M.; PAIXAO, MARCIO W.. Visible-Light-Mediated alpha-Amino Alkylation of Azomethine Imines: An Approach to N-(beta-Aminoalkyl)pyrazolidinones. ORGANIC LETTERS, v. 22, n. 20, p. 7891-7896, OCT 16 2020. (14/50249-8, 15/17141-1, 18/12986-1, 17/10015-6)

PADILLA, ROSA; JORGENSEN, MIKE S. B.; PAIXAO, MARCIO W.; NIELSEN, MARTIN. Efficient catalytic hydrogenation of alkyl levulinates to gamma-valerolactone. GREEN CHEMISTRY, v. 21, n. 19, p. 5195-5200, OCT 7 2019. (16/12622-4, 14/50249-8, 15/17141-1)

DA SILVA, VITOR A. F.; DA SILVA, GUSTAVO P.; MATSUO, BIANCA T.; ALI, AKBAR; DAVIS, REBECCA L.; ZUKERMAN-SCHPECTOR, JULIO; CORREA, ARLENE G.; PAIXAO, MARCIO W.. Synthesis of (Z)-beta-halo alpha,beta-unsaturated carbonyl systems via the combination of halotrimethylsilane and tetrafluoroboric acid. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 17, n. 3, p. 519-526, JAN 21 2019. (16/12622-4, 15/17141-1, 14/50249-8, 16/14560-6)

ALVES, DIEGO; GOLDANI, BRUNA; LENARDAO, EDER J.; PERIN, GELSON; SCHUMACHER, RICARDO F.; PAIXAO, MARCIO W.. Copper Catalysis and Organocatalysis Showing the Way: Synthesis of Selenium-Containing Highly Functionalized 1,2,3-Triazoles. CHEMICAL RECORD, v. 18, n. 5, p. 527-542, MAY 2018. (15/17141-1)

CORREIA, JOSE TIAGO M.; DA SILVA, GUSTAVO PIVA; KISUKURI, CAMILA M.; ANDRE, ELIAS; PIRES, BRUNO; CARNEIRO, PABLO S.; PAIXAO, MARCIO W.. Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor-Acceptor Complex. Journal of Organic Chemistry, v. 85, n. 15, p. 9820-9834, AUG 7 2020. (14/50249-8, 15/17141-1, 18/12986-1, 17/10015-6)

PAIXAO, MARCIO W.. Photoredox Catalysis toward 2-Sulfenylindole Synthesis through a Radical Cascade Process. ORGANIC LETTERS, v. 22, n. 11, p. 4266-4271, JUN 5 2020. (14/50249-8, 17/03120-8, 18/12986-1, 15/17141-1)

DE ALMEIDA RIBEIRO, RUAN STEVAN; MONTEIRO FERREIRA, LUANNE ESTER; ROSSA, VINICIUS; LIMA, CAROLINA G. S.; PAIXAO, MARCIO W.; VARMA, RAJENDER S.; DE MELO LIMA, THIAGO. Graphitic Carbon Nitride-Based Materials as Catalysts for the Upgrading of Lignocellulosic Biomass-Derived Molecules. CHEMSUSCHEM, v. 13, n. 16, JUL 2020. (14/50249-8, 15/17141-1)

FERNANDES, VITOR A.; LIMA, RAFAELY N.; BROTERSON, YOISEL B.; KAWAMURA, MEIRE Y.; ECHEMENDIA, RADELL; DE LA TORRE, ALEXANDER F.; FERREIRA, MARCO A. B.; RIVERA, DANIEL G.; PAIXAO, MARCIO W.. Direct access to tetrasubstituted cyclopentenyl scaffolds through a diastereoselective isocyanide-based multicomponent reaction. CHEMICAL SCIENCE, v. 12, n. 48, SEP 2021. (15/17141-1, 17/01754-0, 14/50249-8, 20/01255-6, 20/10246-0, 19/01973-9)

MENEZES CORREIA, JOSE TIAGO; DA SILVA, GUSTAVO PIVA; ANDRE, ELIAS; PAIXAO, MARCIO WEBER. Photoredox Decarboxylative Alkylation/(2+2+1) Cycloaddition of 1,7-Enynes: A Cascade Approach Towards Polycyclic Heterocycles Using N-(Acyloxy)phthalimides as Radical Source. ADVANCED SYNTHESIS & CATALYSIS, v. 361, n. 24, p. 7-pg., 2019-08-26. (15/17141-1, 17/10015-6, 14/50249-8)

LI, JIANBIN; CAIUBY, CLARICE A. D.; PAIXAO, MARCIO W.; LI, CHAO-JUN. Synthesis of 6-Trifluoromethylphenanthridines through Radical Trifluoromethylation of Isocyanides with Sodium Triflinate under Visible Light. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2018, n. 20-21, SI, p. 2498-2503, JUN 7 2018. (15/17141-1, 14/50249-8)

PIRES, CLAUDIA T. A.; SCODRO, REGIANE B. L.; CORTEZ, DIOGENES A. G.; BRENZAN, MISLAINE A.; SIQUEIRA, VERA L. D.; CALEFFI-FERRACIOLI, KATIANY R.; VIEIRA, LUCAS C. C.; MONTEIRO, JULIA L.; CORREA, ARLENE G.; CARDOSO, ROSILENE F.. Structure-activity relationship of natural and synthetic coumarin derivatives againstMycobacterium tuberculosis. Future Medicinal Chemistry, AUG 2020. (14/50249-8, 13/07600-3, 15/17141-1)

MENEZES CORREIA, JOSE TIAGO; DA SILVA, GUSTAVO PIVA; ANDRE, ELIAS; PAIXAO, MARCIO WEBER. Photoredox Decarboxylative Alkylation/(2+2+1) Cycloaddition of 1,7-Enynes: A Cascade Approach Towards Polycyclic Heterocycles Using N-(Acyloxy)phthalimides as Radical Source. ADVANCED SYNTHESIS & CATALYSIS, AUG 2019. (15/17141-1, 14/50249-8, 17/10015-6)

LIMA, CAROLINA G. S.; MOREIRA, NATALIA M.; PAIXAO, MARCIO W.; CORREA, ARLENE G.. Heterogenous green catalysis: Application of zeolites on multicomponent reactions. CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY, v. 15, n. SI, p. 7-12, FEB 2019. (15/17141-1, 14/50249-8, 17/19940-4, 13/07600-3)

LIMA, CAROLINA G. S.; JORGE, ERLEN Y. C.; BATINGA, LEYLIANE G. S.; LIMA, THIAGO DE M.; PAIXAO, MARCIO W.. ZSM-5 zeolite as a promising catalyst for the preparation and upgrading of lignocellulosic biomass-derived chemicals. CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY, v. 15, n. SI, p. 13-19, FEB 2019. (15/17141-1, 14/50249-8)

CAIUBY, CLARICE A. D.; ALI, AKBAR; SANTANA, VINICIUS T.; LUCAS, FRANCISCO W. DE S.; SANTOS, MARILIA S.; CORREA, ARLENE G.; NASCIMENTO, OTACIRO R.; JIANG, HAO; PAIXAO, MARCIO W.. Intramolecular radical cyclization approach to access highly substituted indolines and 2,3-dihydrobenzofurans under visible-light. RSC ADVANCES, v. 8, n. 23, p. 12879-12886, 2018. (14/50249-8, 15/17141-1, 13/07600-3)

LIMA, CAROLINA G. S.; MONTEIRO, JULIA L.; LIMA, THIAGO DE MELO; PAIXAO, MARCIO WEBER; CORREA, ARLENE G.. Angelica Lactones: From Biomass-Derived Platform Chemicals to Value-Added Products. CHEMSUSCHEM, v. 11, n. 1, p. 25-47, JAN 10 2018. (15/17141-1, 14/50249-8, 13/07600-3)

VIEIRA, LUCAS C. C.; MATSUO, BIANCA T.; MARTELLI, LORENA S. R.; GALL, MAYARA; PAIXAO, MARCIO W.; CORREA, ARLENE G.. Asymmetric synthesis of new gamma-butenolides via organocatalyzed epoxidation of chalcones. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 15, n. 29, p. 6098-6103, AUG 7 2017. (15/17141-1, 14/50249-8, 13/07600-3)

LIMA, THIAGO M.; LIMA, CAROLINA G. S.; RATHI, ANUJ K.; GAWANDE, MANOJ B.; TUCEK, JIRI; URQUIETA-GONZALEZ, ERNESTO A.; ZBORIL, RADEK; PAIXAO, MARCIO W.; VARMA, RAJENDER S.. Magnetic ZSM-5 zeolite: a selective catalyst for the valorization of furfuryl alcohol to gamma-valerolactone, alkyl levulinates or levulinic acid. GREEN CHEMISTRY, v. 18, n. 20, p. 5586-5593, 2016. (15/17141-1)

DE LA TORRE, ALEXANDER F.; ALI, AKBAR; GALETTO, FABIO Z.; BRAGA, ANTONIO L.; DELGADO, JOSE A. C.; PAIXAO, MARCIO W.. One-pot organocatalytic/multicomponent approach for the preparation of novel enantioenriched non-natural selenium-based peptoids and peptide-peptoid conjugates. MOLECULAR DIVERSITY, v. 24, n. 1, p. 1-10, FEB 2020. (15/17141-1, 14/50249-8)

GONCALVES, R.; PAIVA, R. S.; LIMA, T. M.; PAIXAO, M. W.; PEREIRA, E. C.. Carbon nitride/polypyrrole composite supercapacitor: Boosting performance and stability. Electrochimica Acta, v. 368, FEB 1 2021. (15/17141-1, 14/50249-8, 17/11986-5, 17/06536-0, 13/07296-2, 11/10897-2)

DE SOUZA, WANDERSON C.; MATSUO, BIANCA T.; MATOS, PRISCILLA M.; CORREIA, JOSE TIAGO M.; SANTOS, MARILIA S.; KOENIG, BURKHARD; PAIXAO, MARCIO W.. Photocatalyzed Intramolecular [2+2] Cycloaddition of N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides. CHEMISTRY-A EUROPEAN JOURNAL, v. 27, n. 11, JAN 2021. (14/50249-8, 15/17141-1, 20/00556-2, 17/10015-6)

LI, JIANBIN; CAIUBY, CLARICE A. D.; PAIXAO, MARCIO W.; LI, CHAO-JUN. Synthesis of 6-Trifluoromethylphenanthridines through Radical Trifluoromethylation of Isocyanides with Sodium Triflinate under Visible Light. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2018, n. 20-21, p. 6-pg., 2018-06-07. (15/17141-1, 14/50249-8)

LIMA, CAROLINA G. S.; JORGE, ERLEN Y. C.; BATINGA, LEYLIANE G. S.; LIMA, THIAGO DE M.; PAIXAO, MARCIO W.. ZSM-5 zeolite as a promising catalyst for the preparation and upgrading of lignocellulosic biomass-derived chemicals. CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY, v. 15, p. 7-pg., 2019-02-01. (14/50249-8, 15/17141-1)

LIMA, CAROLINA G. S.; MOREIRA, NATALIA M.; PAIXAO, MARCIO W.; CORREA, ARLENE G.. Heterogenous green catalysis: Application of zeolites on multicomponent reactions. CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY, v. 15, p. 6-pg., 2019-02-01. (17/19940-4, 14/50249-8, 13/07600-3, 15/17141-1)

PIRES, CLAUDIA T. A.; SCODRO, REGIANE B. L.; CORTEZ, DIOGENES A. G.; BRENZAN, MISLAINE A.; SIQUEIRA, VERA L. D.; CALEFFI-FERRACIOLI, KATIANY R.; VIEIRA, LUCAS C. C.; MONTEIRO, JULIA L.; CORREA, ARLENE G.; CARDOSO, ROSILENE F.. Structure-activity relationship of natural and synthetic coumarin derivatives againstMycobacterium tuberculosis. Future Medicinal Chemistry, v. 12, n. 17, p. 14-pg., 2020-08-21. (14/50249-8, 13/07600-3, 15/17141-1)

RIVERA, DANIEL G.; PAIXAO, MARCIO W.; CHENG, HN; MARYANOFF, CA; MILLER, BD; SCHMIDT, DG. Interplay between Organocatalysis and Multicomponent Reactions in Stereoselective Synthesis. STEREOCHEMISTRY AND GLOBAL CONNECTIVITY: THE LEGACY OF ERNEST L ELIEL, VOL 2, v. 1258, p. 12-pg., 2017-01-01. (15/17141-1, 14/50249-8)

GONCALVESA, ROGER; PEREIRA, ERNESTO C.. Chemometric Evaluation of Poly(3-hexylthiophene) Electrochemical Aging Path as a Function of Electrochemical Synthesis Variables. Journal of the Brazilian Chemical Society, v. 33, n. 8, p. 10-pg., 2022-08-01. (15/17141-1, 17/06536-0, 11/10897-2, 13/07296-2, 14/50249-8, 17/11986-5)

JORGE, ERLEN Y. C.; LIMA, CAROLINA G. S.; LIMA, THIAGO M.; MARCHINI, LUCAS; GAWANDE, MANOJ B.; TOMANEC, ONDREJ; VARMA, RAJENDER S.; PAIXAO, MARCIO W.. Sulfonated dendritic mesoporous silica nanospheres: a metal-free Lewis acid catalyst for the upgrading of carbohydrates. GREEN CHEMISTRY, v. 22, n. 5, p. 1754-1762, MAR 7 2020. (16/12622-4, 15/17141-1)

LIMA, CAROLINA G. S.; LIMA, THIAGO DE M.; DUARTE, MARCELO; JURBERG, IGOR D.; PAIXAO, MARCIO W.. Organic Synthesis Enabled by Light-Irradiation of EDA Complexes: Theoretical Background and Synthetic Applications. ACS CATALYSIS, v. 6, n. 3, p. 1389-1407, MAR 2016. (13/09680-4, 15/17141-1, 14/50249-8)

CORREIA, JOSE TIAGO M.; FERNANDES, VITOR A.; MATSUO, BIANCA T.; DELGADO, JOSE A. C.; DE SOUZA, WANDERSON C.; PAIXAO, MARCIO WEBER. Photoinduced deaminative strategies: Katritzky salts as alkyl radical precursors. CHEMICAL COMMUNICATIONS, v. 56, n. 4, p. 503-514, JAN 14 2020. (14/50249-8, 19/01973-9, 15/17141-1, 17/10015-6)

DE LA TORRE, ALEXANDER F.; SCATENA, GABRIEL S.; VALDES, OSCAR; RIVERA, DANIEL G.; PAIXAO, MARCIA W.. Ugi reaction-derived prolyl peptide catalysts grafted on the renewable polymer polyfurfuryl alcohol for applications in heterogeneous enamine catalysis. Beilstein Journal of Organic Chemistry, v. 15, p. 1210-1216, JUN 4 2019. (15/17141-1, 14/50249-8)