Book chapters

Application of Copper Chelators in Cancer Therapeutics

Luís M. T. Frija

In Science for Sustainability, Edited by A. J. L. Pombeiro et. al. (25 pages), World Scientific, 2025.

Multivolume book (5 volumes, 44 chapters) celebrating the 20th anniversary of the European Academy of Sciences (EurASc)

Selected as “A World Science Reference”.

(under production)

Synthesis of non-symmetrical 1,2,4,5-tetraoxanes: Past and current routes

Patrícia S. M. Amado, Luís M. T. Frija, Paul M. O’Neill and Maria L. S. Cristiano*

In Synthesis and Applications in Chemistry and Materials, Edited by A. J. L. Pombeiro. pp. 113-159, World Scientific, 2024.

https://doi.org/10.1142/9789811283215_0016 

1,2-Benzisothiazole 1,1-Dioxide (Saccharinate)-Based Compounds: Synthesis, Reactivity and Applications

Luís M. T. Frija*, André L. Fernandes, Bruno Guerreiro and M. Lurdes S. Cristiano

In More Synthetic Approaches to Nonaromatic Nitrogen Heterocycles, Vol. 3, ch. 19, Edited by Ana M. Phillips. United Kingdom, Wiley, 2022.  

https://doi.org/10.1002/9781119757153.ch19

Catalytic Alkane Amidation and Related Reactions

Dmytro S. Nesterov, Luís M. T. Frija, Armando J. L. Pombeiro and Maximilian N. Kopylovich

In Alkane Functionalization, 1st Edition, Chapter 19, 427-448. Eds. A. J. L. Pombeiro and M. F. C. Guedes da Silva, John Wiley & Sons Ltd., 2019.

https://doi.org/10.1002/9781119379256.ch19

Isolation and manipulation of a diterpene from the Portuguese Flora

Carlos A. M. Afonso* and Luís M. T. Frija*

In 100 Organic Chemistry Experiments, IST Press, 25-28, 2011. (ISBN: 978-989-8481-09-2)

istpress.tecnico.ulisboa.pt/produto/100-experiencias-de-quimica-organica/

Photochemistry of Tetrazole Derivatives in Cryogenic Rare Gas Matrices

A. Gómez-Zavaglia, I. D. Reva, Luís M. T. Frija, M. L. S. Cristiano and R. Fausto*

In Photochemistry Research Progress, Chapter 9, 295-324. Editors: Alejandro Sánchez and Sergio J. Gutierrez. Nova Science Publishers, Inc., NY, USA. 2008.

https://www.novapublishers.com/catalog/product_info.php?products_id=7189

Peer-reviewed journal articles

Unanticipated Reactivity Towards Nucleophilic Attack in the Synthesis of Saccharyl-1,3,4-Thiadiazolyl Conjugates: Structure and Mechanistic Insights

Bruno E. C. Guerreiro, Daniel Carvalho, Jaime A. S. Coelho, José A. Paixão,  Luís M. T. Frija* and Maria L. S. Cristiano*

J. Org. Chem., 2025 (Submitted).

Understanding synergistic bridging of MOFs in mechanical energy harvesting through triboelectric generation 

Brij Mohan, Bakhtiyar Najafov, Hongli Wen, Luís M. T. Frija, Alexander A. Solovev, Gurjaspreet Singh,* Armando J. L. Pombeiro, Rakesh K. Gupta,* and Wei Sun*

Journal of Energy Chemistry, 2025 (Accepted).

** HOT PAPER **

Synthesis and structure of novel pyrimidine-thioethers: structural effects on reactivity along with an unpredicted dimethylamination reaction

Inês C. C. Costa, Luís M. T. Frija, André F. Augusto, José A. Paixão* and Maria L. S. Cristiano* 

​ChemPhysChem, 2025, 26, e202500308.

https://doi.org/10.1002/cphc.202500308

A convenient TBHP/Cu(NO3)2∙2.5H2O-mediated oxidation of secundary and benzyl alcohols under microwave irradiation

Luís M. T. Frija*

J. Chem. Sci., 2025, 137, 60.

doi.org/10.1007/s12039-025-02370-1

Hybrid azole-based conjugates as upcoming anticancer and antimicrobial agents

Luís M. T. Frija*, Bruno E. C. Guerreiro, Inês C. C. Costa, Vera M. S. Isca, Lucília Saraiva, Beatriz G. Neves, Mariana Magalhães, Célia Cabral, Maria L. S. Cristiano and Patrícia Rijo* 

Exploration of Drug Science, 2023, 1, 420-434.

https://doi.org/10.37349/eds.2023.00028 

In an era where the Chemistry has to be green! Red Alert!

Luís M. T. Frija*

Insights in Chemistry & Biochemistry, 2023, 2(4), 1.

http://dx.doi.org/10.33552/ICBC.2023.02.000542 

​Synthesis of non-symmetrical dispiro 1,2,4,5-tetraoxanes and 1,2,4-trioxanes catalyzed by Silica Sulfuric Acid 

Patrícia S. M. Amado, Luís M. T. Frija, Jaime A. S. Coelho, Paul M. O’Neill* and Maria L. S. Cristiano* 

J. Org. Chem., 2021, 86, 10608-10620.

https://doi.org/10.1021/acs.joc.1c01258

Solvent-free Oxidation of Benzyl Alcohols Catalysed by a Tetrazole-saccharinate Zn(II) Complex under Microwave Radiation: the role of the Ligand and the Reaction Mechanism

Luís M. T. Frija*, André L. Fernandes, M. Lurdes S. Cristiano and Armando J. L. Pombeiro 

J. Mol. Struct., 2020, 1222, 128831.

https://doi.org/10.1016/j.molstruc.2020.128831

Well-defined Nickel(II) Tetrazole-saccharinate Complex as Homogeneous Catalyst on the Reduction of Aldehydes: Scope and Reaction Mechanism

Luís M. T. Frija*, Bruno G. M. Rocha, Maxim L. Kuznetsov, Lília I. L. Cabral, M. Lurdes S. Cristiano and Armando J. L. Pombeiro

Pure & Applied  Chemistry, 2020, 92, 151-166.

https://doi.org/10.1515/pac-2019-0220

​In vitro Assessment of Antimicrobial, Antioxidant and Cytotoxic Properties of Saccharin‑Tetrazolyl and ‑Thiadiazolyl Derivatives; The Simple Dependence of the pH Value on Antimicrobial Activity

Luís M. T. Frija*, Epole Ntungwe, Przemysław Sitarek, Joana M. Andrade, Monika Toma, Tomasz Śliwiński, Lília Cabral, M. Lurdes S. Cristiano, Patrícia Rijo* and Armando J. L. Pombeiro 

Pharmaceuticals, 2019, 12, 167.

http://dx.doi.org/10.3390/ph12040167 

** HOT PAPER **

Synthesis, Structure and Cytotoxicity of a Novel Sulphanyl-Bridged Thiadiazolyl-Saccharinate Conjugate: The Relevance of S...N Interaction

L. Cabral, E. Brás, M. Henriques, C. Marques, Luís M. T. Frija, L. Barreira, J. A. Paixão, R. Fausto*, M. L. S. Cristiano* 

Chem. Eur. J., 2018, 24, 3251-3262. 

​https://doi.org/10.1002/chem.201705319

Organocatalyzed oxidation of benzyl alcohols by a tetrazole-amino-saccharin: A combined experimental and theoretical (DFT) study 

Luís M. T. Frija*, Maxim L. Kuznetsov, Bruno G.M. Rocha, Lília Cabral, M. Lurdes S. Cristiano, Maximilian N. Kopylovich, Armando J. L. Pombeiro

Molecular Catalysis, 2017, 442, 57-65.

http://dx.doi.org/10.1016/j.mcat.2017.09.003 

Proteomic insights on the metabolism of Penicillium janczewskii during the biotransformation of the plant terpenoid labdanolic acid

Isabel Martins, Adélia Varela, Luís M. T. Frija, Mónica A. S. Estevão, Sébastien Planchon, Jenny Renaut, Carlos A. M. Afonso and Cristina S. Pereira*

Front. Bioeng. Biotechnol., 2017, 5:45, 1-12.

https://doi.org/10.3389/fbioe.2017.00045

Building 1,2,4-Thiadiazole: Ten Years of Progress

Luís M. T. Frija*, Armando J. L. Pombeiro, Maximilian N. Kopylovich*

Eur. J. Org. Chem., 2017, 2670-2682.

https://doi.org/10.1002/ejoc.201601642

Copper(II) and cobalt(II) tetrazole-saccharinate complexes as effective catalysts for oxidation of secondary alcohols 

Luís M. T. Frija*, E. C. B. A. Alegria, M. Sutradhar, M. Lurdes S. Cristiano, Amin Ismael, Maximilian N. Kopylovich, Armando J. L. Pombeiro*

J. Mol. Catal. A: Chem., 2016, 425, 283-290.

http://dx.doi.org/10.1016/j.molcata.2016.10.023

Coordination Chemistry of Thiazoles, Isothiazoles and Thiadiazoles

Luís M. T. Frija*, Armando J. L. Pombeiro, Maximilian N. Kopylovich*

Coord. Chem. Rev., 2016, 308, 32-55.

https://doi.org/10.1016/j.ccr.2015.10.003

Supported Acid-catalyzed Flash Vacuum Thermolysis on the Valorisation of Labdanum Resin

Luís M. T. Frija* and Carlos A. M. Afonso* 

Biomass & Bioenergy, 2014, 71, 363-369.

https://doi.org/10.1016/j.biombioe.2014.09.020 

Isolation, analytical quantification and seasonal variation of labdanolic acid from the Portuguese-grown Cistus ladaniferus

André N. C. Martins, Svilen P. Simeonov, Luis M. T. Frija*, Raquel Viveiros, Anita Lourenço, Mara S. da Silva, Teresa Casimiro, Carlos A. M. Afonso*

Ind. Crop. Prod., 2014, 60, 226-232.

https://doi.org/10.1016/j.indcrop.2014.06.012

Genesis of rare molecules using light-induced reactions of matrix-isolated tetrazoles

Luís M. T. Frija*, M. L. S. Cristiano, A. Gómez-Zavaglia, I. D. Reva, R. Fausto 

J. Photochem. Photobiol. C: Photochem Rev., 2014, 18, 71-90.

https://doi.org/10.1016/j.jphotochemrev.2013.09.001

Short Synthesis of the Natural Product 3beta-Hydroxy-labd-8 (17)-en-15-oic Acid via Microbial Transformation of Labdanolic Acid

Luís M. T. Frija*, Helga Garcia, Cátia Rodrigues, Isabel Martins, Nuno R. Candeias, Vânia André, M. Teresa Duarte, Cristina Silva Pereira* and Carlos A. M. Afonso*

Phytochem. Lett., 2013, 6, 165-169.

https://doi.org/10.1016/j.phytol.2012.12.005 

Amberlyst®-15: a Reusable Heterogeneous Catalyst for the Dehydration of Tertiary Alcohols 

Luís M. T. Frija* and Carlos A. M. Afonso*

Tetrahedron, 2012, 68, 7414-7421.

https://doi.org/10.1016/j.tet.2012.06.083 

Sigmatropic Rearrangements in 5-Allyloxytetrazoles

Luís M. T. Frija, I. Reva, D. V. Coelho, A. Ismael, R. Fausto and M. L. S. Cristiano*

Org. Biomol. Chem., 2011, 9, 6040-6054.

https://doi.org/10.1039/C1OB05460K

Isolation, Chemical and Bio-transformation Routes of Labdane-type Diterpenes

Luís M. T. Frija*, Raquel F. M. Frade* and Carlos A. M. Afonso*

Chemical Reviews, 2011, 111, 4418-4452. 

https://doi.org/10.1021/cr100258k

Photochemical Transformations of Tetrazole Derivatives: Applications in Organic Synthesis

Luís M. T. Frija, Amin Ismael and M. L. S. Cristiano*

Molecules, 2010, 15, 3757-3774.

https://doi.org/10.3390/molecules15053757

Synthesis and Structure of Novel Benzisothiazole-tetrazolyl Derivatives for Potential Application as Nitrogen Ligands

Luís M. T. Frija, R. Fausto, Rui M. S. Loureiro and M. L. S. Cristiano*

J. Mol. Catal. A: Chem., 2009, 305, 142-146.

https://doi.org/10.1016/j.molcata.2008.12.007

Photochemistry of Tetrazole Derivatives in Cryogenic Rare Gas Matrices

A. Gómez-Zavaglia, I. D. Reva, Luís M. T. Frija, M. L. S. Cristiano and R. Fausto*

Chemical Physics Research Journal, 2009, Vol. 1, Issue 4, 221-250.

http://www.novapublishers.org/catalog/product_info.php?products_id=7195

Photochemistry of 5-Allyloxy-tetrazoles: Steady-state and Laser Flash-Photolysis Study

Luís M. T. Frija, I. V. Khmelinskii, I. D. Reva, C. Serpa, R. Fausto and M. L. S. Cristiano*

Org. Biomol. Chem., 2008, 6, 1046-1055.

https://doi.org/10.1039/B718104C

UV-Induced Photochemistry of Matrix-Isolated 1-Phenyl-4-Allyl-Tetrazolone

Luís M. T. Frija, I. D. Reva, A. Gómez-Zavaglia, M. L. S. Cristiano and R. Fausto*

Photochem. Photobiol. Sci., 2007, 6, 1170-1176.

https://doi.org/10.1039/B703961A

Photochemistry and Vibrational Spectra of Matrix-Isolated 5-Ethoxy-1-Phenyl-1H-Tetrazole

Luís M. T. Frija, I. D. Reva, A. Gómez-Zavaglia, M. L. S. Cristiano and R. Fausto

J. Phys. Chem. A., 2007, 111, 2879-2888.

https://doi.org/10.1021/jp068556h

Photochemical Ring-opening and Intramolecular Hydrogen Shift Reactions in Sulfur Analogues of α-Pyrone 

S. Breda, I. Reva, L. Lapinski, M. L. Cristiano, L. Frija and R. Fausto*

J. Phys. Chem. A., 2006, 110, 6415-6425.

https://doi.org/10.1021/jp061139k

Infrared Spectrum and UV-Induced Photochemistry of 5-Methoxy-1-Phenyl-Tetrazole Isolated in Solid Argon

A. Gómez-Zavaglia, I. D. Reva, L. Frija, M. L. Cristiano and R. Fausto* 

J. Photochem. Photobiol. A: Chem., 2006, 180, 175-183.

https://doi.org/10.1016/j.jphotochem.2005.10.012

Molecular Structure, Vibrational Spectra and Photochemistry of 5-Mercapto-1-Methyltetrazole in Solid Argon

A. Gómez-Zavaglia, I. D. Reva, L. Frija, M. L. Cristiano and R. Fausto*

J. Mol. Struct., 2006, 786, 182-192.

https://doi.org/10.1016/j.molstruc.2005.08.019

Mechanistic Investigations into the Photochemistry of 4-Allyl-tetrazolones in Solution; A New Approach to the Synthesis of 3,4-Dihydro-pyrimidinones

Luís M. T. Frija, Igor V. Khmelinskii and M. Lurdes S. Cristiano*

J. Org. Chem., 2006, 71, 3583-3591.

https://doi.org/10.1021/jo060164j

Photochemistry of 1-Phenyl-Tetrazolone Isolated in Solid Argon

A. Gómez-Zavaglia, I. D. Reva, L. Frija, M. L. Cristiano and R. Fausto*

J. Photochem. Photobiol. A: Chem., 2006, 179, 243-255.

https://doi.org/10.1016/j.jphotochem.2005.08.021

Palladium-catalysed Reduction of Heteroaromatic Naphthyl Ethers: Structural Effects on Reactivity

Luís M. T. Frija, M. Lurdes S. Cristiano*, Emanuel M. O. Guimarães, Nélson C. Martins and Jamie F. Bickley

J. Mol. Catal. A: Chem., 2005, 242, 241-250.

https://doi.org/10.1016/j.molcata.2005.08.022

Novel Efficient Synthesis of 3,4-Dihydro-6-substituted-3-phenylpyrimidin-2(1H)-ones

Luís M. T. Frija, Igor V. Khmelinskii and M. Lurdes S. Cristiano* 

Tetrahedron Lett., 2005, 46, 6757-6760.

https://doi.org/10.1016/j.tetlet.2005.07.101

Molecular Structure, Vibrational Spectra and Photochemistry of 2-Methyl-2H-Tetrazol-5-Amine in Solid Argon

A. Gómez-Zavaglia, I. D. Reva, L. Frija, M. L. Cristiano and R. Fausto*

J. Phys. Chem. A., 2005, 109, 7967-7976.

https://doi.org/10.1021/jp0517706

Heteroaromatic Benzyl Ethers as Intermediates for Heterogeneous Catalytic Transfer Hydrogenolysis of Benzyl Alcohols

Nuna C. P. Araújo, Amadeu F. Brigas*, M. Lurdes S. Cristiano*, Luís M. T. Frija, Emanuel M. O. Guimarães and Rui M. S. Loureiro 

J. Mol. Catal. A: Chem., 2004, 215, 113-120.

https://doi.org/10.1016/j.molcata.2003.12.033

Vibrational Spectra and Structure of 1-Phenyltetrazole and 5-Chloro-1-Phenyltetrazole. A Combined Study by Low Temperature Matrix Isolation and Solid State FTIR Spectroscopy and DFT Calculations

Susana C. S. Bugalho, Leszek Lapinski, M. Lurdes S. Cristiano, Luís M. T. Frija and Rui Fausto*

Vib. Spectrosc., 2002, 30, 213-225.

https://doi.org/10.1016/S0924-2031(02)00028-0

Theses 

​Luís Miguel Teodoro Frija, Title: Investigation of Structural Effects on the Reactivity of Heterocyclic Bioactive Compounds

Ph.D. Thesis, Chemistry – Organic Chemistry,  University of Algarve, 2008.

http://hdl.handle.net/10400.1/856

Luís Miguel Teodoro Frija, Title: Design and Synthesis of Compounds with Potential Biological Activity

Scientific Final Project Thesis, Degree in Chemistry (Tese de projecto final da Licenciatura em Química),  University of Algarve, 2001.