Review
Chemistry, Medicinal
Lizeth Arce-Ramos, Juan-Carlos Castillo, Diana Becerra
Summary: This review provides an overview of the synthesis and exhaustive biological studies conducted on benzo[b]furan derivatives, highlighting their potential as anticancer, antibacterial, and antifungal agents, as well as their applications in drug discovery and medicinal chemistry.
Article
Biochemistry & Molecular Biology
Balati Hasimujiang, Shengsheng Lin, Chengwei Zheng, Yong Zeng, Zhixiong Ruan
Summary: A mild, practical method for the synthesis of various C-3 selenylated benzo[b]furan derivatives was developed via electrooxidation-promoted intramolecular cyclization of alkynes. The method exhibited high selectivity, high yield, and could easily be scaled up, providing rapid access to a diverse range of selenylated benzo[b]furans.
Article
Chemistry, Multidisciplinary
Zhihui Wang, Lei Wang, Zhiming Wang, Pinhua Li, Yicheng Zhang
Summary: A practical synthesis method of alpha-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions has been developed, achieving high yields without additional photocatalysts under sunlight irradiation.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Organic
Allyn T. Londregan, John M. Curto, Emma Hastry, Colin R. Rose, Simon Berritt
Summary: In this study, a general and convenient procedure for the synthesis of azinones is presented. Cyclopropylmethanol is used as a protecting group and surrogate for hydroxyl in various azines. The corresponding azinones can be formed and isolated in excellent yields after acidic deprotection under mild reaction conditions. More than 20 examples, along with reaction optimization, scope, and mechanism, are discussed.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Biquan Xiong, Wenli Shang, Weifeng Xu, Yu Liu, Ke-Wen Tang, Wai-Yeung Wong
Summary: A facile and efficient method for the synthesis of alpha-diarylmethyl substituted phenols has been developed using phosphoric acid as the catalyst and water as the green solvent. Addition of TEMPO as an additive allows for the generation of diaryl-substituted para-quinone methides. These reactions exhibit high functional group tolerance, good to excellent yields, and unique selectivity, providing a new method for organic synthesis.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Chang Wen, Chuan Wu, Ruiqiang Luo, Qinghan Li, Feng Chen
Summary: A highly efficient and simple method for synthesizing 2-substituted benzo[b]furans has been developed using palladium-catalyzed cross-coupling reaction, with isolated yields ranging from 23% to 97%. Substrates with electron-donating or electron-withdrawing groups in 2-halobenzo[b]furans can also successfully produce products.
SYNTHESIS-STUTTGART
(2021)
Article
Geochemistry & Geophysics
Xin Wang, Meijun Li, Taotao Yang, Bang Zeng, Yang Shi, Xiaoqiang Liu, Youjun Tang
Summary: The distribution and geochemical significance of benzo[b]naphthofurans (BNFs) and benzo[b]naphthothiophenes (BNTs) in delta-lacustrine mudstone samples from the Bei-buwan Basin, South China Sea were studied. The relative content of BNF and BNT isomers increases with burial depth and maturity, indicating higher thermostability. The parameters BNFR and BNTR correlate well with vitrinite reflectance, suggesting their potential as indicators for assessing source rock maturity. BNFs and DBF show a similar origin in an oxic environment with higher plant input, while BNFs may be converted to other compounds at high thermal maturity. The absolute concentrations of BNTs increase with maturity, indicating a thermal origin, possibly generated from phenylnaphthalene isomers during catagenesis.
Article
Chemistry, Organic
Xia Lin, Chengtao Fang, Xiaolei Huang, Xiaohui Xiao
Summary: A novel method for synthesizing 1,1,2-tribromoethyl arenes was developed in this work, with the additional discovery that under strong acidic conditions, a selectivity switch can lead to the formation of alpha-bromoketones.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Marco Ballarotto, Mario Solinas, Andrea Temperini
Summary: A new metal-free synthesis approach for substituted 6H-benzo[c]chromenes has been developed, using a highly regioselective intermolecular Diels-Alder cycloaddition as the key step. The three-step synthetic sequence showed good yields up to 94% over two steps. The mechanism, investigated through DFT calculations, confirmed the experimental results in terms of regioselectivity and reactivity tendencies.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Caria Evans, William J. Berkey, Christopher W. Jones, Stefan France
Summary: A Zr-catalyzed synthesis of tetrasubstituted 1,3-diacylpyrroles has been reported using N-acyl alpha-aminoaldehydes and 1,3-dicarbonyl compounds. The reaction showed high yields (up to 88%) and the products were found to be hydrolytically and configurationally stable. The N-acyl alpha-aminoaldehydes were easily prepared from corresponding alpha-amino acids. The reaction could accommodate various substrate types and a range of 1,3-dicarbonyls, including aldehyde derived from a l,l-dipeptide, an in situ generated aldehyde, and an N-acylated glucosamine.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Min Liu, Kelu Yan, Jiangwei Wen, Ning Zhang, Xinyu Chen, Xue Li, Xiu Wang
Summary: This study presents a simple and efficient method for the C-H chalcogenylation of benzo[d]imidazo[5,1-b]thiazoles with disulfides or diselenides using phenyliodine(III) bis(trifluoroacetate) (PIFA) as a catalyst under mild and easy to operate conditions. The protocol provides a rapid and straightforward pathway for the construction of diverse organochalcogen derivatives.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Vasiliy M. Muzalevskiy, Zoia A. Sizova, Vasiliy V. Panyushkin, Vyacheslav A. Chertkov, Victor N. Khrustalev, Valentine G. Nenajdenko
Summary: A novel class of trifluoromethyl building blocks was efficiently synthesized and a possible reaction mechanism was proposed. This strategy allows for the synthesis of trifluoromethylated pyrazolines and pyrazoles, enabling the synthesis of derivatives of known drugs.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Claudia Feberero, Cintia Virumbrales, Carlos Sedano, Lorena Renedo, Samuel Suarez-Pantiga, Roberto Sanz
Summary: A straightforward and transition metal-free one-pot protocol for synthesizing halobenzo[b]furans has been developed using easily available starting materials. The researchers fine-tuned the different steps involved to achieve a successful one-pot procedure and synthesized a wide variety of new halobenzo[b]furans.
Article
Chemistry, Multidisciplinary
Xing Liu, Dali Yang, Zhao Liu, Yunkun Wang, Yichang Liu, Shengchun Wang, Pengjie Wang, Hengjiang Cong, Yi-Hung Chen, Lijun Lu, Xiaotian Qi, Hong Yi, Aiwen Lei
Summary: Oxidation-induced strategy using highly active radical cation intermediates has shown unique reactivity for activating inert chemical bonds. Understanding the structure and reactivity patterns of radical cation intermediates is crucial for mechanistic studies and the development of new reactions. In this study, the structure and properties of indole radical cations were investigated using time-resolved transient absorption spectroscopy, in situ electrochemical UV-vis, and in situ Density functional theory (DFT) calculations. The insights gained from the properties of indole radical cations were used to successfully develop regioselective annulations of indoles under electrochemical oxidation conditions, leading to the synthesis of furo[2,3-b]indolines and furo[3,2-b]indolines with high yields and regioselectivities. These mechanistic insights will further advance oxidation-induced indole functionalizations.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Beibei Zhang, Xiaoxian Li, Xuemin Li, Fengxia Sun, Yunfei Du
Summary: The study demonstrates that the reaction of 2-alkynylanisoles/sulfides with SOCl2 and DMSO can conveniently synthesize biologically active 3-(methylthio)-benzo[b]furans/thiophenes, with DMSO acting as a solvent and sulfur source that can be replaced with DMSO-d(6) to incorporate the SCD3 moiety into the 3-position of the heterocyclic frameworks.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Editorial Material
Chemistry, Multidisciplinary
Jose I. Santos, Ivan Rivilla, Fernando P. Cossio, F. Javier Garcia-Garcia, Jon M. Matxain, Marek Grzeliczak, Shobeir K. S. Mazinani, Jesus M. Ugalde, Vladimir Mujica
Article
Chemistry, Multidisciplinary
Albert Granados, Ivan Rivilla, Fernando P. Cossio, Adelina Vallribera
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Organic
Albert Granados, Alexandr Shafir, Ana Arrieta, Fernando P. Cossio, Adelina Vallribera
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Ivan Rivilla, Mikel Odriozola-Gimeno, Antonio Aires, Ana Gimeno, Jesus Jimenez-Barbero, Miguel Torrent-Sucarrat, Aitziber L. Cortajarena, Fernando P. Cossio
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Review
Biochemistry & Molecular Biology
Fernando P. Cossio, Manel Esteller, Maria Berdasco
CURRENT OPINION IN CHEMICAL BIOLOGY
(2020)
Article
Chemistry, Multidisciplinary
Maria de Gracia Retamosa, Andrea Ruiz-Olalla, Maddalen Agirre, Abel de Cozar, Tamara Bello, Fernando P. Cossio
Summary: This study investigates the emergent catalytic properties of dimeric unnatural prolines compared to their monomeric analogues, showing that the dimers exhibit additive stereocontrol relative to their monomeric components and possess the ability to promote Michael reactions, a catalytic property not present in the constituent monomers.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Fernando P. Cossio, Abel de Cozar, Miguel A. Sierra, Luis Casarrubios, Jaime G. Muntaner, Bimal K. Banik, Debasish Bandyopadhyay
Summary: Computational-experimental analysis has determined that the stereochemistry of the Staudinger reaction is closely associated with the nature of the imine, affecting the nucleophilic attack and electrocyclization steps. The impact of energetically accessible in situ isomerization patterns and substituents of the imine on the reaction's stereochemistry has been analyzed kinetically, with results supporting experimental findings.
Article
Chemistry, Multidisciplinary
Jacopo Dosso, Beatrice Bartolomei, Nicola Demitri, Fernando P. Cossio, Maurizio Prato
Summary: The synthesis and isolation of a rare pi-extended diamagnetic phenazine dication have been achieved by oxidizing a phenanthrene-based dihydrophenazine precursor. The resulting dication showed an aromatic distorted structure and electrochromic change in the UV-vis spectrum. The dication was proven to be aromatic theoretically and exhibited dual reactivity, contracting to a p-extended triarylimidazolinium or reducing to the dihydrophenazine precursor, providing insights into the reactivity and properties of extended dicationic PAHs. The reversible conformational change of the molecule opens potential applications as molecular switches and actuators.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Abel de Cozar, Ana Arrieta, Fernando P. Cossio
Summary: Computational studies have shown that the regiochemistry of electrophilic cyclization reactions depends on the position of the triple bond in alkynes. Terminal alkynyl groups lead to six-membered rings, while internal alkynes yield five-membered rings through different electrophilic cyclization mechanisms. The regiochemistry is determined by the minimization of Pauli repulsion, rather than two-electron interactions. This pattern is also observed in biomimetic reactions leading to steroid scaffolds.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Applied
Raquel Hidalgo-Leon, Nerea Alberro, Fernando P. Cossio, Jose Miguel Sansano, Maria de Gracia Retamosa
Summary: The highly enantioselective organocatalytic synthesis of spirocyclic compounds by Diels-Alder reactions using cyclic 2,5-dienones as precursors and different nitroalkenes as dienophiles is described. Cinchonidine-based primary amine catalyst and benzoic acid co-catalyst enable the construction of spiro compounds containing three stereogenic centres with good yields and excellent diastereo- and enantioselectivities. Computational methods have been used to investigate the plausible reaction mechanism.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Multidisciplinary
Abel de Cozar, Ana Arrieta, Iosune Arrastia, Fernando P. Cossio
Summary: This review focuses on the relationship between higher-order electrocyclizations and Woodward-Hoffmann rules. It analyzes the applications of 10π-18π electrocyclizations in synthesis and discusses the importance of computational tools in understanding experimental selectivity.
Review
Cell Biology
Giorgio Frega, Fernando P. Cossio, Jesus M. Banales, Vincenzo Cardinale, Rocio I. R. Macias, Chiara Braconi, Angela Lamarca
Summary: This study conducted a systematic literature review and meta-analysis to investigate the expression levels of PD-1, PD-L1, and other immune-related biomarkers in biliary tract cancer patients. The results showed that approximately 26% of BTC patients expressed PD-L1, with TMB-H and MSI molecular phenotypes being less common. However, further research is needed to identify reliable biomarkers, especially for patients with proficient mismatch repair tumors.
Article
Chemistry, Multidisciplinary
Gabriel Merino, Miquel Sola, Israel Fernandez, Cina Foroutan-Nejad, Paolo Lazzeretti, Gernot Frenking, Harry L. Anderson, Dage Sundholm, Fernando P. Cossio, Marina A. Petrukhina, Jishan Wu, Judy I. Wu, Albeiro Restrepo
Summary: Aromaticity is a deeply rooted concept in chemistry, but there is no consensus on its definition due to the many attributes associated with it. This perspective aims to reflect the current state and future direction of the aromaticity research community.
Article
Chemistry, Physical
Zoraida Freixa, Ivan Rivilla, Francesc Monrabal, Juan J. Gomez-Cadenas, Fernando P. Cossio
Summary: This article introduces the basic design criteria of bicolour fluorescent molecular sensors and discusses the chemical behavior and electronic features of different fluorescent responses, including intramolecular charge transfer, excimer/exciplex complex formation, and Förster resonance energy transfer. Moreover, changes in the electronic properties of the fluorophore upon metal binding and the possibility of generating fluorescent bicolour indicators that can capture metal cations in the gas phase and at solid-gas interfaces are also discussed.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2021)
Article
Chemistry, Organic
Julio Lopez, Ivan Velazco-Cabral, Eloy Rodriguez-deLeon, Clarisa Villegas Gomez, Francisco Delgado, Joaquin Tamariz, Ana Arrieta, Fernando P. Cossio, Miguel A. Vazquez
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
