Article
Chemistry, Organic
Rulin Zhao, Zhenqiu Hong, Bei Wang, James Kempson, Lyndon Cornelius, Jianqing Li, Yi-Xin Li, Arvind Mathur
Summary: A simple and efficient method for the synthesis of N1-substituted-4-nitropyrazole-5-carboxylates has been developed, with excellent regioselectivity and good yields.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Martin Linden, Silja Hofmann, Antonia Herman, Nicole Ehler, Robin M. M. Baer, Siegfried R. R. Waldvogel
Summary: This study presents the first electrochemical approach for the direct synthesis of pyrazolines and pyrazoles from easily accessible hydrazones and dipolarophiles. The method allows for large-scale production and even conversion of highly sensitive alkenes. The use of a biphasic system with sodium iodide as a supporting electrolyte and mediator is cost-effective. Mechanistic insight is provided by the isolation of key intermediates, and the synthesis of a commercial herbicide safener further highlights the significance of this reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Ivan S. Odin, Anton Yu Chertov, Olga B. Grigor'eva, Alexander A. Golovanov
Summary: The interaction between 1,5-diaryl-3-X-pent-4-yn-1-ones and arylhydrazines resulted in the synthesis of 3-aryl-5-arylethynyl-1-phenyl-4,5-dihydro-1H-pyrazoles with good yields. These compounds exhibited significant fluorescent abilities, with emission maximum wavelengths ranging from 453-465 nm and 363-400 nm.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Dezhi Lin, Yunfang Liu, Hongyu Yang, Xiao Zhang, Huaming Sun, Yajun Jian, Weiqiang Zhang, Jianming Yang, Ziwei Gao
Summary: This research presents a highly selective C-O activation approach for the synthesis of cross-conjugated enynones using alpha, beta-unsaturated triazine esters as acyl electrophiles. Under base and phosphine ligand-free conditions, NHC-Pd(II)-Allyl precatalyst alone efficiently catalyzed the cross-coupling reaction of alpha, beta-unsaturated triazine esters with terminal alkynes, yielding 31 cross-conjugated enynones with diverse functional groups. This method showcases the potential of triazine-mediated C-O activation for the preparation of highly functionalized ketones.
Review
Chemistry, Multidisciplinary
Teymour Vahedpour, Maryam Hamzeh-Mivehroud, Salar Hemmati, Siavoush Dastmalchi
Summary: This review article classifies and presents different methods for the synthesis of 2-pyrazolines using hydrazine derivatives, including catalytic methods, multicomponent reactions, and two-component reactions. It discusses various aspects such as catalyst efficiency, green chemistry, cost-effectiveness, and also summarizes important applications of 2-pyrazolines.
Article
Chemistry, Organic
Radik N. Itakhunov, Ivan S. Odin, Dmitry M. Gusev, Stanislav A. Grabovskiy, Kareem Gordon, Anna V. Vologzhanina, Sergey A. Sokov, Ilya M. Sosnin, Alexander A. Golovanov
Summary: The condensation of 1,5-disubstituted pent-1-en-4-yn-1-ones with arylhydrazines in acidified alcohol leads to the formation of arylhydrazones with traces of pyrazoline impurities. The cyclization of arylhydrazones into 1,5-disubstituted 3-styrylpyrazoles occurs only in high-boiling polar solvents. The reactions between 2-hydrazinylpyridine and 1,5-disubstituted pent-1-en-4-yn-1-ones yield 2-(5-styryl-3-phenyl-1H-pyrazol-1-yl)pyridines. A gram-scale synthesis method has been developed for these compounds, and their fluorescence properties and complexation with Hg2+, Cd2+, and Pb2+ ions have been investigated.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Hui Huang, Yiru Pu, Dikai Zhu, Chaozheng Zhang, Jirui Yang, Changqun Liu, Xin Zhang, Feiyan Tao, Mei-Mei Li, Jun Lu
Summary: We presented a general approach for synthesizing isoxazole-containing pyrazolines and pyrazoles through a [3 + 2] cycloaddition reaction. The process involved the in situ generation of nitrile imines and their reaction with 3-methyl-4-nitro-5-alkenyl isoxazoles, resulting in a regioselective synthesis of trans-configured isoxazole-substituted pyrazolines. Aromatization of the cycloadducts with the catalysis of MnO2 or SnCl2 provided access to poly-substituted pyrazoles with excellent selectivity depending on the catalyst used. The method also allowed for the one-pot synthesis of isoxazole-substituted pyrazoles. (c) 2022 Elsevier Ltd. All rights reserved.
Review
Chemistry, Multidisciplinary
Aditi Tiwari, Anjaneyulu Bendi, Anirudh Singh Bhathiwal
Summary: Chalcones are a group of aromatic ketones with enone moiety that exhibit a wide range of biological activities, and when synthesized into pyrazolines, their biological activity can be enhanced. This study reviews the chemistry of various chalcone-based pyrazolines and their derivatives up to 2021.
Review
Biochemistry & Molecular Biology
Vera L. M. Silva, Artur M. S. Silva
Summary: This review describes the properties, synthetic approaches, and versatile applications of vinylpyrazoles as building blocks in organic chemistry. It covers their reactivity in various reactions, including cycloadditions, polymerizations, halogenation, hydrohalogenation, and transition-metal-catalyzed reactions. The review provides an overview of the current state of the art and future prospects in the chemistry of vinylpyrazoles.
Article
Biochemistry & Molecular Biology
Gita Matuleviciute, Egle Arbaciauskiene, Neringa Kleiziene, Vilija Kederiene, Greta Ragaite, Migle Dagiliene, Aurimas Bieliauskas, Vaida Milisiunaite, Frank A. Slok, Algirdas Sackus
Summary: A series of novel heterocyclic amino acid compounds were developed and regioselectively synthesized as N-Boc protected esters, serving as achiral and chiral building blocks. The structures of these compounds were confirmed through H-1, C-13, and N-15-NMR spectroscopy and HRMS investigation.
Article
Chemistry, Organic
Anna S. Zalivatskaya, Alexander A. Golovanov, Irina A. Boyarskaya, Mariya A. Kruykova, Olesya V. Khoroshilova, Aleksander V. Vasilyev
Summary: Linear-conjugated enynones were cyclized into alkylidene indanes in triflic acid TfOH. The reactions involved hydroarylation of the acetylene bond followed by further cyclization. Plausible reaction mechanisms were proposed based on DFT calculations.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yuanyuan Ren, Ransong Ma, Yang Feng, Ke-Hu Wang, Junjiao Wang, Danfeng Huang, Xiaobo Lv, Yulai Hu
Summary: Difluoroacetohydrazonoyl bromides are stable in air and can be used as good difluoromethyl building blocks for the construction of CF2H-substituted pyrazoline and pyrazole compounds through [3+2] cycloaddition with electron-deficient olefins under mild conditions. The method offers mild reaction conditions, good regioselectivity, broad substrate scopes, and easy operation.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Shuai Zhang, Xinhua Duan, Pengfei Li
Summary: The study presented a mild, rapid copper-catalyzed diborylation reaction for the synthesis of stereodefined multifunctionalized beta,gamma-unsaturated ketones. Fine control of chemo-, regio-, Z/E and diastereoselectivity was achieved, expanding the substrate scope and proposing a possible catalytic cycle to explain the selectivity.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Yifan Ping, Taiwei Chang, Jianbo Wang
Summary: The rhodium-catalyzed directed acyl C-H bonds carbene insertion reaction of 2-aminobenzaldehydes with conjugated enynones has been achieved, providing a series of α-furyl ketone derivatives with good functional group tolerance in moderate to good yields. Carbene migratory insertion is proposed as the key step in this transformation.
Article
Chemistry, Multidisciplinary
Valerie A. A. Kuehl, Alexander H. H. Cleveland, Christopher J. J. Snyder, David E. E. Chavez
Summary: Three novel energetic materials were synthesized, which are liquids at room temperature with melting points ranging from -60.2 to -38.6 degrees C. They were fully characterized and compared to the starting materials and nitroglycerin in terms of sensitivity to impact and thermal stability.
Article
Crystallography
Alexey A. Artemjev, Artyom A. Astafiev, Anna V. Vologzhanina, Alexey S. Kubasov, Gleb M. Burkin, Alexander S. Novikov, Andreii S. Kritchenkov, Anatoly A. Kirichuk, Alexander G. Tskhovrebov
Summary: Novel triarylazoimidazoles and their group 12 metal complexes, containing strong electron donors or acceptors, were synthesized and characterized. The complexes exhibited red photo-luminescence emission in solution, and showed antibacterial activity against Gram-positive microorganism S. aureus and Gram-negative microorganism E. coli.
Letter
Chemistry, Organic
Nadezhda M. Andriyashina, Stanislav A. Grabovskii, Rustam L. Safiullin
Summary: This study aimed to investigate the thermal stability of 1,1-dihydroperoxycyclohexane in different solvents. The rate constants and activation parameters were measured to determine the reaction rate and the peroxide's monomolecular decomposition rate in the presence of 2-naphthol. The use of DHPC as a radical initiator requires considering its reactions with solvents and/or monomers, as well as its monomolecular decomposition with the formation of free radicals.
LETTERS IN ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
P. A. Buikin, A. V. Vologzhanina, D. E. Arkhipov, A. A. Korlyukov
Summary: The anionic complexes LSi(Cat(R))(2) were studied using quantum chemistry methods, and it was found that the substituents in the catecholate phenyl ring and the L group have weak influence on the geometry of the coordination environment of the silicon atom. The electron-withdrawing effect and the number of substituents in the catecholate ligands determine the ionization potentials. The formation of oxidized forms of the complexes is characterized by weakening of certain Si-O bonds and shortening of others. The analysis shows that one of the catecholate ligands is less sensitive to interaction with free radicals.
RUSSIAN CHEMICAL BULLETIN
(2022)
Article
Chemistry, Inorganic & Nuclear
Alexander S. Belov, Valentin V. Novikov, Anna V. Vologzhanina, Alexander A. Pavlov, Artem S. Bogomyakov, Yan V. Zubavichus, Roman D. Svetogorov, Genrikh E. Zelinskii, Yan Z. Voloshin
Summary: This study investigates the fast crystallization and structural transformation of a cobalt (II) complex. The complex undergoes a temperature-induced spin crossover and its behavior is influenced by solvent and crystal polymorphism. The findings provide insights into the synthesis and properties of cobalt complexes.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Organic
Stanislav A. Grabovskii, Nadezhda M. Andrijashina, Alexandr N. Lobov, Arkadiy V. Antipin, Rustam L. Safiullin
Summary: A facile and efficient method for the oxidation of sulfides to sulfoxides without using any catalysts is reported. The method achieved high yields (> 95%) of sulfoxides under mild conditions. The low cost and ready accessibility of gem-dihydroperoxides make them attractive oxidants for chemical synthesis.
Article
Chemistry, Organic
Eugene P. P. Kramarova, Pavel V. V. Dorovatovskii, Anna V. V. Vologzhanina, Alexander A. A. Korlyukov
Summary: An X-ray diffraction study was conducted on the transesterification product of N-methyl-N-(trimethoxysilylmethyl)acetamide with 4,5-dibromobenzene-1,2-diol. It was found that the coordination polyhedron of the silicon atom in the anionic complex was a distorted octahedron disordered by the superposition of Delta and Λ optical isomers. Various hydrogen donor groups in the bis(cyclohexyl)ammonium cations, solvent ethanol molecules, and non-coordinated 4,5-dibromobenzene-1,2-diol led to the formation of H-bonded chains, while dibromobenzenediol also participated in stacking interactions.
Article
Pharmacology & Pharmacy
Artem O. Surov, Ksenia V. Drozd, Anna G. Ramazanova, Andrei V. Churakov, Anna V. Vologzhanina, Elizaveta S. Kulikova, German L. Perlovich
Summary: Polymorphism is a common phenomenon in molecular crystals and has a significant impact on drug development. This study obtained and characterized a new polymorphic form of the drug carbamazepine (CBZ) cocrystal with methylparaben (MePRB), as well as a channel-like cocrystal with highly disordered coformer molecules, using various analytical methods. The structural analysis revealed a close resemblance between the novel form II and previously reported form I of the [CBZ + MePRB] cocrystal. The discovered form II showed superior thermodynamic stability and dissolution performance, making it a more promising solid form for pharmaceutical development.
Article
Biochemistry & Molecular Biology
Alexander A. Korlyukov, Adam. I. Stash, Alexander R. Romanenko, Damian Trzybinski, Krzysztof Wozniak, Anna V. Vologzhanina
Summary: The nature and strength of interactions in Lamivudine were studied using crystallography and calculations. The crystal structure and charge density distribution were determined for the drug. The effects of intramolecular and intermolecular interactions were compared, and the energy contributions to crystal and ligand-receptor binding were evaluated.
Article
Chemistry, Multidisciplinary
T. V. Baulina, I. Yu. Kudryavtsev, M. P. Pasechnik, A. G. Matveeva, S. V. Matveev, A. V. Vologzhanina, A. N. Turanov, V. K. Karandashev, V. K. Brel
Summary: New tetraphosphoryl tripodal ligands with different linker lengths (n = 3, 4) were synthesized on the triphenylphosphine oxide platform [2-Ph2P(O)(CH2)(n)OC6H4](3)PO. Their composition and structure were determined using elemental analysis, IR and multinuclear (H-1, C-13, and P-31) NMR spectroscopy, and X-ray diffraction analysis. The extraction properties of the ligands were studied by extracting microamounts of f-elements from an aqueous phase into 1,2-dichloroethane.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Alexander A. Korlyukov, Petr A. Buikin, Pavel V. Dorovatovskii, Anna V. Vologzhanina
Summary: This study investigates the crystal structures of various solid forms of Abiraterone, an active metabolite used to treat prostate cancer. The structures include pure Abiraterone, Abiraterone acetate, cocrystals of Abiraterone acetate with carboxylic acids, and a pyridinium-containing salt. The crystal structure of (HAbirOH)Br & BULL; H2O is determined through X-ray diffraction, and the charge density distribution of Abiraterone is analyzed using NoSpherA2 refinement. Noncovalent interactions in this salt are discussed using molecular Voronoi and Hirshfeld surfaces. Crystal packing similarities of AbirOH in this salt and previously reported solids are also analyzed.
STRUCTURAL CHEMISTRY
(2023)
Article
Pharmacology & Pharmacy
Petr Buikin, Anna Vologzhanina, Roman Novikov, Pavel Dorovatovskii, Alexander Korlyukov
Summary: Abiraterone acetate is a commonly used therapeutic agent for prostate cancer, but its poor solubility limits its effectiveness. In this study, d-metal complexes with Abiraterone acetate were obtained to improve its solubility and investigate its interaction with heme. The results showed that Abiraterone acetate can form stable complexes with dications and act as a bridge ligand in reactions with silver(I) nitrate. The bonding energies between Abiraterone acetate and these cations were found to be higher than those between metal atoms and water molecules.
Article
Chemistry, Inorganic & Nuclear
Alexander S. Chuprin, Alexander A. Pavlov, Anna V. Vologzhanina, Pavel V. Dorovatovskii, Anton V. Makarenkov, Valentina A. Ol'shevskaya, Semyon V. Dudkin, Yan Z. Voloshin
Summary: A multistep synthetic strategy for polytopic carboranyl-containing (semi)clathrochelate metal complexes involving template synthesis, transmetallation, amide condensation, and 1,3-dipolar cycloaddition reactions is developed. Various precursors were obtained through transmetallation and macrobicyclization, and further condensation reactions led to the formation of carboranosemiclathrochelates and phthalocyaninatoclathrochelates. The resulting complexes were characterized by various techniques and exhibited interesting coordination geometries.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Organic
Radik N. Itakhunov, Ivan S. Odin, Dmitry M. Gusev, Stanislav A. Grabovskiy, Kareem Gordon, Anna V. Vologzhanina, Sergey A. Sokov, Ilya M. Sosnin, Alexander A. Golovanov
Summary: The condensation of 1,5-disubstituted pent-1-en-4-yn-1-ones with arylhydrazines in acidified alcohol leads to the formation of arylhydrazones with traces of pyrazoline impurities. The cyclization of arylhydrazones into 1,5-disubstituted 3-styrylpyrazoles occurs only in high-boiling polar solvents. The reactions between 2-hydrazinylpyridine and 1,5-disubstituted pent-1-en-4-yn-1-ones yield 2-(5-styryl-3-phenyl-1H-pyrazol-1-yl)pyridines. A gram-scale synthesis method has been developed for these compounds, and their fluorescence properties and complexation with Hg2+, Cd2+, and Pb2+ ions have been investigated.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ekaterina N. Zorina-Tikhonova, Anna K. Matyukhina, Aleksandr S. Chistyakov, Anna V. Vologzhanina, Alexander A. Korlyukov, Natalia Gogoleva, Veronika A. Novikova, Ekaterina Belova, Elena A. Ugolkova, Alyona A. Starikova, Denis Korchagin, Konstantin A. Babeshkin, Nikolay N. Efimov, Mikhail A. Kiskin, Igor L. Eremenko
Summary: A series of Ba-M-II complexes with allylmalonic acid anions were synthesized and characterized, revealing their different structures and magnetic properties. The complexes also undergo polymerization of the allyl fragment.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Inorganic & Nuclear
Varvara V. Avdeeva, Anna V. Vologzhanina, Alexey S. Kubasov, Nailya S. Akhmadullina, Oleg N. Shishilov, Elena A. Malinina, Nikolay T. Kuznetsov
Summary: Gold(III) complexation with the octadecahydrido-eicosaborate anion [B20H18](2-) was investigated for the first time. The reaction of gold(III) complexes [Au(L)Cl-2]BF4 (L = bipy, phen) with [B20H18](2-) resulted in the formation of complexes [Au(L)Cl-2](2)[B20H18]. X-ray diffraction studies revealed weak B-H...Au interactions between the compounds. It is worth noting that more reactive anions [BnHn](2-) (n = 10, 12) in similar reactions with gold(III) complexes led to gold mirror reactions.