Article
Chemistry, Organic
Nikolay Shcherbakov, Dmitry Dar'in, Vadim Yu Kukushkin, Alexey Yu Dubovtsev
Summary: The reaction between benzofuroxans and N-allylynamides catalyzed by gold leads to the formation of 3-azabicyclo[3.1.0]hexan-2-imines under mild conditions with high functional group tolerance. The obtained cyclopropanated products serve as a useful synthetic platform with easily modulated substitution pattern through postmodifications. The intramolecular cyclopropanation of gold alpha-imino carbene intermediates is proposed as a key step in the catalytic cycle.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Ouidad Lahtigui, Dan Forster, Coralie Duchemin, Nicolai Cramer
Summary: In this study, a flexible two-step protocol for the efficient and selective synthesis of rigid saturated nitrogen-containing scaffolds was disclosed. The method involves alkenyl C-H functionalization and cyclization reactions mediated by C*Rh-III and Cp*Ir-III catalysts, respectively, leading to the synthesis of diverse substituted 3-azabicyclo[3.1.0]hexanes.
Article
Chemistry, Multidisciplinary
Qiuyu Li, Yunchu Zhang, Pengyun Liu, Jing Zhong, Baihui Gong, Hequan Yao, Aijun Lin
Summary: We present a mild and efficient method for synthesizing chiral 3-azabicyclo[3.1.0]hexanes via a Pd-catalyzed asymmetric 5-exo-trig cyclization/cyclopropanation/carbonylation of 1,6-enynes. This reaction shows excellent regio- and enantioselectivities, forming three C-C bonds, two rings, two adjacent quaternary carbon stereocenters, and one C-O/C-N bond.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Daisuke Sato, Akira Tsubouchi, Yuichiro Watanabe, Keiichi Noguchi, Kazunori Miyamoto, Masanobu Uchiyama, Akio Saito
Summary: The activation of alkyne pi-bonds by transition metal complexes is well studied for the cycloisomerization of enynes into bicyclo[3.1.0]hexanes, enabling the introduction of carbon and oxygen functional groups. However, the cycloisomerization of enynones through the activation of carbonyl groups into bicyclo[3.1.0]hexanes has not yet been achieved. In this study, we report the aluminum halide-mediated cycloisomerization of 7-en-2-ynones into halogenated bicyclo[3.1.0]hexanes.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Yuto Shimazaki, Ayumi Osawa, Yoshiaki Nakao
Summary: In this study, we report a novel iridium/aluminum cooperative catalysis for the direct bridge-head C(sp(3))-H borylation. The reaction gives good yields with moderate to complete site selectivities and allows for the synthesis of enantioenriched alkylboronate products. The synthetic utility of the reaction is further demonstrated by rapid diversifications without any loss of the stereochemical information.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Siqi Wang, Alexander S. Filatov, Stanislav Lozovskiy, Stanislav Shmakov, Olesya Khoroshilova, Anna G. Larina, Stanislav Selivanov, Vitali M. Boitsov, Alexander Stepakov
Summary: A multi-component reaction for synthesizing spirocyclic heterocycles has been developed, providing easy access to molecules with specific motifs under mild conditions. Theoretical studies have shown the mechanism of formation and transformations of azomethine ylide precursors in the reaction. The synthesized compounds were evaluated for their anti-tumor activity against cervical carcinoma cells in vitro.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Michail N. Elinson, Anatoly N. Vereshchagin, Yuliya E. Ryzhkova, Mikhail P. Egorov
Summary: Electrocatalytic cyclization of 6-hydroxy-5-[(2-hydroxy6-oxocyclohex-1-en-1-yl)(aryl)methyl]-1,3-dimethylpyrimidine-2,4-(1H,3H)-diones in alcohols in the presence of sodium halides results in selective formation of substituted spirobarbituric dihydrofurans in 82-93% yields. The crystal structure of 3-(3-bromophenyl)1',3',6,6-tetramethyl-3,5,6,7-tetrahydro-2',4-dihydrospiro [benzofuran-2,5'-pyrimidine]-2',4,4',6'(1'H,3'H)tetraone has been confirmed by X-ray diffraction data.
MENDELEEV COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Michail N. Elinson, Yuliya E. Ryzhkova, Anatoly N. Vereshchagin, Fedor Ryzhkov, Varvara M. Kalashnikova, Viktor A. Korolev, Mikhail P. Egorov
Summary: In this study, a facile and efficient electrochemical method was used to synthesize functionalized unsymmetrical spiro(indole-3,4'-pyrano[3,2-b]pyranes) in an undivided cell using a multicomponent reaction in n-propanol solvent. Molecular docking analysis revealed that the synthesized compounds have the potential to be protein ligands with potential pharmacological activities.
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Alexander S. Goloveshkin, Natalia D. Lenenko, Mikhail I. Buzin, Vladimir I. Zaikovskii, Alexander V. Naumkin, Alexandre S. Golub
Summary: By combining MoS2 layered compounds with organic cations, the structure of 1T-MoS2 can be stabilized, resulting in improved catalytic performance for hydrogen evolution reaction (HER) from water. Certain organic cations tightly bound to sulfide sheets in a sulfuric acid electrolyte can increase the 1T/2H ratio and maintain catalyst activity in the long term. These findings offer a new approach for the rational design of efficient non-precious electrocatalysts based on 1T-MoS2 for hydrogen production.
INTERNATIONAL JOURNAL OF HYDROGEN ENERGY
(2023)
Article
Biochemistry & Molecular Biology
Dmitriy S. Yambulatov, Julia K. Voronina, Alexander S. Goloveshkin, Roman D. Svetogorov, Sergey L. Veber, Nikolay N. Efimov, Anna K. Matyukhina, Stanislav A. Nikolaevskii, Igor L. Eremenko, Mikhail A. Kiskin
Summary: A new 1D-coordination polymer with different phases at room temperature was obtained. The structural phase transition of the compound was observed as the temperature decreased, accompanied by an increase in crystal packing density. The compound exhibited slow magnetic relaxation in a magnetic field of 1000 Oe.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Review
Biochemistry & Molecular Biology
Nikita A. Frolov, Anatoly N. Vereshchagin
Summary: This article summarizes recent scientific literature on intra- and intermolecular reactions leading to the formation of various piperidine derivatives. It also covers the pharmaceutical applications of synthetic and natural piperidines, as well as the latest scientific advances in the discovery and biological evaluation of potential drugs containing piperidine moiety. The review aims to assist both novice researchers and experienced scientists in the synthesis of biologically active piperidines.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Physical
Makarii I. Kozlov, Kirill M. Kuznetsov, Alexander S. Goloveshkin, Andrei Burlakin, Maria Sandzhieva, Sergey V. Makarov, Elena Ilina, Valentina V. Utochnikova
Summary: An approach to increase the efficiency of europium-based OLEDs was proposed through the formation of a mixed-ligand complex. By designing a series of europium complexes and optimizing the solution deposition process, including host selection and variation of solvent and deposition parameters, the luminance of the OLEDs was significantly increased. The maximum luminance of the Eu-based OLED reached up to 700 cd/m(2), which is one of the highest values for a solution-processed Eu-based OLED. Finally, the stability of the OLED was investigated.
Article
Chemistry, Organic
Yuliya E. Ryzhkova, Fedor V. Ryzhkov, Oleg I. Maslov, Michail N. Elinson
Summary: In this paper, the multicomponent reaction of salicylaldehyde, malononitrile dimer, and 2-phenyl-5-(trifluoromethyl)-2,4-dihydro-3H-pyrazol-3-one in dimethyl sulfoxide was studied. The reaction yielded 2,4-diamino-5-(5-hydroxy-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile with good yield. The previously unknown chromeno[2,3-b]pyridine derivative was characterized using various spectroscopy techniques.
Article
Biochemistry & Molecular Biology
Yuliya E. Ryzhkova, Fedor V. Ryzhkov, Michail N. Elinson, Anatoly N. Vereshchagin, Roman A. Novikov, Artem N. Fakhrutdinov
Summary: Some of the most important transformations in organic chemistry are rearrangement reactions, which increase synthetic efficiency and molecular complexity. The development of synthetic strategies involving rearrangement reactions has been a hot topic in the chemistry community. In this work, the thermal rearrangement of 7,9-dihalogen-substituted 5-(2-hydroxy-6-oxocyclohexyl)-5H-chromeno[2,3-b]pyridines in DMSO was proposed. Previously unknown compounds were synthesized with high yields (90-99%) and their structures were confirmed using 2D-NMR spectroscopy.
Article
Biochemistry & Molecular Biology
Alexander S. Goloveshkin, Natalia D. Lenenko, Alexander V. Naumkin, Alexandre S. Golub
Summary: This study presents a simple method for immobilizing the antiseptic drug miramistin (MR) between molybdenum disulfide sheets. Two hybrid layered compounds (LCs) with different thicknesses of organic layers were prepared and analyzed. The obtained structural models revealed the noncovalent interaction network of MR molecules confined in the two-dimensional spacing surrounded by sulfide sheets. The results provide a comprehensive understanding of the assembly of MR and MoS2 and may contribute to the development of novel photothermal therapeutic agents.
Article
Chemistry, Multidisciplinary
Michail N. Elinson, Yuliya E. Ryzhkova, Fedor V. Ryzhkov, Varvara M. Kalashnikova, Oleg I. Maslov
Summary: A new type of chemical one-pot Knoevenagel-Michael reaction was discovered, leading to the synthesis of substituted bispyrazolone cyclopropanes with excellent yields and stereoselectivity. This efficient and convenient process utilizes aldehydes and pyrazolin-5-one as starting materials and has potential applications in the biomedical field. The mild conditions and simple isolation procedure further enhance the attractiveness of this one-pot reaction.
MONATSHEFTE FUR CHEMIE
(2023)
Review
Chemistry, Multidisciplinary
F. V. Ryzhkov, Y. E. Ryzhkova, M. N. Elinson, M. P. Egorov
Summary: This review provides an overview of the methods for synthesizing cognitive enhancers used as drugs to improve cognitive abilities or restore mental health in patients with pathological conditions. It summarizes information about trials and effectiveness of cognitive enhancers. The review specifically focuses on synthetic routes to compounds acting on cholinergic receptors, particularly muscarinic and nicotinic receptor ligands.
RUSSIAN CHEMICAL BULLETIN
(2023)
Review
Chemistry, Medicinal
Evgeniya A. Saverina, Nikita A. Frolov, Olga A. Kamanina, Vyacheslav A. Arlyapov, Anatoly N. Vereshchagin, Valentine P. Ananikov
Summary: In the past, the focus was mainly on individual antibacterial activity, but now there is a shift towards affecting more complex cellular frameworks and using multiple strategies to combat biofilms at different stages. Quaternary ammonium compounds (QACs) play a key role in these treatments. This review summarizes the literature data on the effectiveness of using commercially available and newly synthesized QACs, as well as synergistic treatment techniques based on them. It also discusses the development and application of antimicrobial coatings to prevent biofilm formation on various surfaces.
ACS INFECTIOUS DISEASES
(2023)
Article
Chemistry, Organic
Yuliya E. E. Ryzhkova, Fedor V. V. Ryzhkov, Michail N. N. Elinson
Summary: In recent years, the application of privileged structures has become a powerful approach in the discovery of new biologically active molecules. Ion pairing is a strategy used to enhance the permeation of ionized topical drugs. A convenient and efficient method for the synthesis of triethylammonium 2-(3-hydroxy-2-oxoindolin-3-yl)-5,5-dimethyl-3-oxocyclohex-1-en-1-olate has been developed. The presented protocol includes an aldol reaction and the formation of an ammonium salt. Triethylamine is both a reactant and a catalyst in the process. The structure of the synthesized title compound has been established by H-1, C-13-NMR and IR spectroscopy, mass spectrometry, and elemental analysis.
Article
Chemistry, Multidisciplinary
Dmitry Tsyganov, Dmitry Demchuk, Olga I. Adaeva, Leonid D. Konyushkin, Mikhail E. Minyaev, Victor N. Khrustalev, Victor V. Semenov
Summary: A general synthetic method for obtaining methoxy analogues of coenzymes Q with various chain lengths at the quinone ring was developed using natural (polymethoxy)(methylenedioxy)allylbenzenes. The key step in the synthesis of the target 1,4- and 1,2-poly-alkoxyquinones was identified as the Baeyer-Villiger rearrangement of (methylenedioxy)benzaldehydes into phenols, followed by facile oxidation to quinones with the methylenedioxy moiety opening.
MENDELEEV COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Victor E. Kalugin, Olga I. Adaeva, Dmitry V. Demchuk, Victor V. Semenov
Summary: Efficient preparative procedures for the synthesis of 2,3-disubstituted 5,6,7,8-tetraalkoxyquinolines starting from tetraalkoxybenzaldehydes are described. The tetraalkoxybenzaldehydes can be obtained from plant (polyalkoxy)(allyl)benzenes, which are secondary metabolites of parsley and dill seeds.
MENDELEEV COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
