Article
Biochemistry & Molecular Biology
Jekaterina Ivanova, Morteza Abdoli, Alessio Nocentini, Raivis Zalubovskis, Claudiu T. Supuran
Summary: A series of 1,2,3-benzoxathiazine-2,2-dioxides with various substituents were synthesized and their inhibitory activity on carbonic anhydrase isoforms was investigated. Some of the derivatives showed promising selectivity towards specific isoforms.
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Wang Feng, Huang Danfeng, Zhao Pengfei, Yang Ming, Han Tongyu, Wang Kehu, Wang Junjiao, Su Yingpeng, Hu Yulai
Summary: The allylation of benzol[e][1,2,3]oxathiazine-2,2-dioxides with allyl bromides promoted by tin powder was investigated. The reaction proceeded smoothly with high yields for various substrates. The resulting allylated products underwent N-allylation reaction and then ring closing metathesis reaction, leading to the formation of diallylated products and cyclic derivatives of benzol[e][1,2,3]oxathiazine-2,2-dioxides, respectively.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Gongyi Liu, Kui Tian, Chenzong Li, Cai You, Xuefeng Tan, Heng Zhang, Xumu Zhang, Xiu-Qin Dong
Summary: A highly efficient catalytic system based on inexpensive transition metal nickel was developed for the asymmetric hydrogenation of challenging cyclic alkenyl sulfones. The study provided a reasonable catalytic mechanism for the nickel-catalyzed asymmetric hydrogenation, showing that the hydrogenation products could originate from H-2 through the insertion of Ni-H and subsequent hydrogenolysis.
Article
Chemistry, Organic
Nieves P. Ramirez, Guillaume Pisella, Jerome Waser
Summary: The gem-aminoalkynylation of fluorinated diazo compounds catalyzed by Cu(I) salt allows the synthesis of propargylic amines with broad functional group tolerance. Both electron-rich and electron-poor anilines can be used as nucleophiles, while alkyl-, aryl-, and silyl-substituted EthynylBenziodoXoles (EBX) can serve as electrophiles in this three-component reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Oleksandr Shalimov, Eduard Rusanov, Petro Onys'ko
Summary: A new method utilizing N-chlorosulfonyltrichloroacetimidoyl chloride has been developed for the synthesis of 1,4,2-benzodithiazine and 1,2,3-benzoxathiazine scaffolds. Nucleophilic substitution and intramolecular sulfonylation reactions were employed for selective functionalization of thiophenols and phenols. The synthesized 1,4,2-benzodithiazine-1,1-dioxides exhibited growth-stimulating activity in both monocotyledonous and dicotyledonous plants.
Article
Chemistry, Multidisciplinary
S. Banuprakash Goud, Raju Lal Dhakar, Sampak Samanta
Summary: A novel method for the aziridination reaction of cyclic N-sulfonyl imines with alpha-aryl-substituted vinyl azides using an in situ generated photoactive copper(I)-complex as catalyst under blue-LEDs light irradiation is reported. This method is mild, sustainable, and practical, providing the desired sulfamidate-fused aziridines with good yields and excellent diastereoselectivities. The newly developed metal-free ring-expansion techniques allow the synthesis of pharmacologically attractive compounds.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Fu-Xiaomin Liu, Weijie Chen, Lei Ma, Kui Cheng, Zhi Zhou, Wei Yi
Summary: Here, an efficient and solvent-tunable Rh(iii)-catalyzed [5+2] annulation of N-benzo[d]imidazole indolines with 2,2-difluorovinyl tosylate has been achieved, showing an unusual 1,2-regioselectivity for the construction of monofluorinated and gem-difluorinated benzodiazepines, which exhibit potent anti-tumor activity against different cancer cell lines. Overall, this work provides a powerful complement to both C-H activation chemistry and anti-tumor lead discovery.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Debasmita Mondal, Gargi Pal, Chinmay Chowdhury
Summary: The cyclisation reactions between tert-butyl propargyl carbonates and 2-aminotosyl benzamides or sulphonamides catalysed by Pd(0) deliver key components of biologically active compounds, 1,4-benzodiazepin-5-ones or sultam derivatives. However, propargyl carbonates substituted at acetylenic carbon are required for the stereoselective formation of the products with 2-amino benzamides/sulphonamides.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Amparo Sanz-Marco, Daniel Esperilla, Marc Montesinos-Magraner, Carlos Vila, M. Carmen Munoz, Jose R. Pedro, Gonzalo Blay
Summary: A Cu(ii)/BOX complex catalyst was used for the enantioselective addition of difluorinated silyl enol ethers to acylpyridine N-oxides. The reaction produced difluorinated chiral tertiary alcohols, which are of great interest in medicinal chemistry. The reaction had good to excellent yields and high enantioselectivities. The stereochemical outcome of the reaction was explained by DFT calculations.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Materials Science, Multidisciplinary
Miguel Gavara-Edo, Francisco Javier Valverde-Munoz, Rosa Cordoba, M. Carmen Munoz, Javier Herrero-Martin, Jose Antonio Real, Eugenio Coronado
Summary: In this study, three new neutral Fe(II) SCO molecules belonging to the {Fe[H2B(pz)(2)](2)(L)} family were synthesized, and their crystallographic structure and magnetic properties were investigated. These compounds exhibited thermal- and light-induced SCO transitions with different degrees of cooperativity and effectiveness. Furthermore, two of the compounds were demonstrated to be sublimable, forming homogeneous thin films that retained the chemical integrity of the original molecules. SCO/2D horizontal hybrid devices based on CVD-graphene were successfully produced using these films, enabling the detection of the thermal SCO transition through the electric properties of CVD-graphene.
JOURNAL OF MATERIALS CHEMISTRY C
(2023)
Article
Chemistry, Inorganic & Nuclear
Alejandro Orellana-Silla, Ruben Turo-Cortes, Victor Rubio-Gimenez, Carlos Bartual-Murgui, Rob Ameloot, Carlos Marti-Gastaldo, M. Carmen Munoz, Jose Antonio Real
Summary: This study investigates the influence of chemical functionalization on the magnetic and adsorption properties of porous Fe-II coordination polymers. The results show that the chemical functionalization leads to significant changes in the magnetic transition temperature and curve shape, as well as higher adsorption capacities. The structural reasons behind these variations are determined through single crystal-to-single crystal transformations.
INORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Applied
Laura Carceller-Ferrer, Gonzalo Blay, M. Carmen Munoz, Jose R. Pedro, Carlos Vila
Summary: A diastereo- and enantioselective synthesis of spirocyclopropylpyrazolones was achieved through a Michael/alkylation cascade reaction of 4-arylidenepyrazol-5-ones with diethyl 2-bromomalonate catalyzed by (DHQ)(2)AQN. The corresponding spirocyclic compounds were obtained selectively with yields of 30-83%, diastereoselectivities ranging from 60:40 to >95:5, and enantiomeric excess of 26-93% under mild reaction conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Jaume Rostoll-Berenguer, Gonzalo Blay, Jose R. Pedro, Carlos Vila
Summary: Financial support is acknowledged from grant PID2020-116944GB funded by MCIN/AEI/10.13039/501100011033, and by ERDF A way of making Europe and CIAICO/2021/147 funded by Conselleria d'Innovacio, Universitat, Ciencia i Societat Digital. J.R.-B. thanks the Ministerio de Ciencia, Innovacion y Universidades for a FPU predoctoral contract (FPU17/00688). C.V. thanks the RyC contract (RYC-2016-20187) funded by MCIN/AEI/10.13039/501100011033 and by European Union NextGeneration EU/PRTR. Access to NMR, MS, and X-ray facilities from the Servei Central de Suport a la Investigacio Experimental (SCSIE)-UV is also acknowledged.
Article
Chemistry, Inorganic & Nuclear
Maksym Seredyuk, Kateryna Znovjyak, Francisco Javier Valverde-Munoz, M. Carmen Munoz, Volodymyr M. Amirkhanov, Igor O. Fritsky, Jose Antonio Real
Summary: This paper reports a series of neutral trans-thiocyanate mononuclear spin crossover complexes based on tetradentate ligands L. These complexes exhibit thermal-induced spin crossover behavior and the formation of photo-generated metastable high-spin phases.
INORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Ramon Jimenez-Robles, Marta Izquierdo, Vicente Martinez-Soria, Laura Marti, Alicia Monleon, Jose David Badia
Summary: Superhydrophobic PVDF membranes with high water contact angles (WCA) were achieved through oxygen plasma activation and functionalization. The surface modifications led to morphological changes and a pillar-like structure with higher surface porosity. The plasma-treated membranes maintained their superhydrophobic performance even after long-term operations.
Article
Chemistry, Multidisciplinary
Jaume Rostoll-Berenguer, Victor Garcia-Garcia, Gonzalo Blay, Jose R. Pedro, Carlos Vila
Summary: This study describes an organophotoredox 1,6-radical addition of 3,4-dihidroquinoxalin-2-ones to para-quinone methides catalyzed by Fukuzumi's photocatalyst under the irradiation of a HP Single LED (455 nm). The corresponding 1,1-diaryl compounds bearing a dihydroquinoxalin-2-one moiety (20 examples) were obtained with good to excellent yields under mild reaction conditions. Several experiments were carried out to propose a reaction mechanism.
ACS ORGANIC & INORGANIC AU
(2023)
Article
Chemistry, Multidisciplinary
Borja Ortin-Rubio, Jaume Rostoll-Berenguer, Carlos Vila, Davide M. Proserpio, Vincent Guillerm, Judith Juanhuix, Inhar Imaz, Daniel Maspoch
Summary: In this study, a generalized net-clipping approach is proposed for predicting the topology of metal-organic frameworks (MOFs) constructed from less-symmetric ligands. The approach generates less-symmetric nets with less-connected linkers through the deconstruction of more-symmetric and more-connected linkers in edge-transitive nets. The researchers successfully applied this approach to different types of linkers, resulting in several new derived and clipped nets. The feasibility of using net-clipping to predict clipped nets is supported by literature examples and new experimental additions, demonstrating the significance of this method in the rational design of new reticular materials.
Article
Chemistry, Organic
Ricardo Toran, Eduardo Portillo, Amparo Sanz-Marco, Carlos Vila, Gonzalo Blay
Summary: We report the enantioselective arylation of isoxazolin-5-ones using a bifunctional squaramide derived from Cinchona alkaloid as a catalyst. The reaction proceeds with high yields and excellent enantioselectivities, resulting in isoxazolin-5-ones featuring an arylated quaternary stereocenter. This study represents the first application of o-QDIs as arylating reagents in asymmetric catalysis.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Materials Science, Multidisciplinary
Alejandro Orellana-Silla, Manuel Meneses-Sanchez, Ruben Turo-Cortes, Victor Rubio-Gimenez, Giel Arnauts, M. Carmen Munoz, Rob Ameloot, Carlos Bartual-Murgui, Jose Antonio Real
Summary: Functionalization of spin crossover porous coordination polymers (PCPs) with hydrogen-bonding active groups is an efficient strategy for the study of multifunctional materials. The interaction of guests with the host framework can improve the cooperativity of the spin crossover (SCO) and further enhance its properties. Comprehensive magneto-structural studies are still needed to understand the role of guests in the enhancement of the SCO properties.
JOURNAL OF MATERIALS CHEMISTRY C
(2023)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
