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

• Grant number: 15/17141-1
• Support Opportunities: Regular Research Grants
• Duration: November 01, 2015 - 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)

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)

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.; 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)

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)

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)

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)

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)

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, 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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)