Article
Chemistry, Organic
Enrique Gil de Montes, Matteo A. Tallarida, Ana T. Carmona, Claudio D. Navo, Inmaculada Robina, Pilar Elias-Rodriguez, Gonzalo Jimenez-Oses, Antonio J. Moreno-Vargas
Summary: This study highlights the regioselective rearrangement of aminyl radicals, leading to the formation of novel bicyclic diazabicyclic compounds. The research explores the impact of different bridgehead atoms and substituents on the rearrangement reaction, while providing a detailed mechanistic proposal supported by computational studies.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Daniel Matuszczyk, Yu Jin Lee, Seongsoo Kang, Piotr J. Chmielewski, Joanna Cybinska, Dongho Kim, Marcin Stepien
Summary: A series of propeller-shaped donor-acceptor compounds were successfully synthesized via nucleophilic substitution reactions, showing efficient charge transfer especially between ortho-positioned donors and acceptors. This study is of significance for understanding the process of electron transfer.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Jacob P. Norman, Nathaniel G. Larson, Emily D. Entz, Sharon R. Neufeldt
Summary: A highly selective method for cross-coupling reactions at the C4 position of 2,4-dichloropyridines was developed using a sterically hindered N-heterocyclic carbene ligand. The reaction showed high selectivity and broad scope, allowing for the formation of C4-C(sp2) and C4-C(sp3) bonds using organoboron, -zinc, and -magnesium reagents. Ligand-free conditions were also found to enhance the selectivity of the Suzuki coupling reaction by an order of magnitude, enabling the first C5-selective cross-couplings of 2,5-dichloropyridine and 2,5-dichloropyrimidine.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Pham Duy Quang Dao, Chan Sik Cho
Summary: A class of trinuclear N-fused hybrid scaffolds, benzo[4,5]imidazo[1,2-a]benzo[4,5]imidazo[1,2-c]quinazolines and -pyrimidines, were successfully synthesized in good yields using a microwave-assisted coupling and cyclization process with 2-(2-Bromoaryl)- and 2-(2-bromovinyl)benzimidazoles as building blocks. The reaction is believed to proceed through an initial C(sp(2))-N coupling followed by a nucleophilic aromatic substitution (SNAr) and cyclization, resulting in the extrusion of alcohols.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Anna E. Vartanova, Andrey Yu Plodukhin, Nina K. Ratmanova, Ivan A. Andreev, Mikhail N. Anisimov, Nikita B. Gudimchuk, Victor B. Rybakov, Irina I. Levina, Olga A. Ivanova, Igor Trushkov, Igor Alabugin
Summary: This study expands the limits of endo-tet cyclizations by showing that donor-acceptor cyclopropanes can form a seven-membered ring via a genuine 6-endo-tet process, yielding tetrahydrobenz[b]azepin-2-ones. Control of the stereochemistry of the products through reaction conditions allows access to both diastereomers.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Applied
Surajit Duari, Subrata Biswas, Arnab Roy, Srabani Maity, Abhishek Kumar Mishra, Aguinaldo R. Souza, Asma M. Elsharif, Nelson H. Morgon, Srijit Biswas
Summary: In this study, a catalytic synthetic strategy was developed to access various N-functionalized heterocyclic derivatives. The reaction involves the direct nucleophilic substitution of alcohols followed by X to N alkyl group migration. Methyl trifluoromethanesulfonate was found to be an efficient catalyst for this reaction. The mechanism was elucidated through experiments and DFT calculations.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Physical
Nina K. Ratmanova, Ivan A. Andreev, Vitaly A. Shcherbinin, Olga A. Ivanova, Irina I. Levina, Victor N. Khrustalev, Igor V. Trushkov
Summary: Triple-role thiocyanate-containing protic ionic liquids (PILs) were used as a regenerable solvent, a Bronsted acid catalyst, and a nucleophile source to achieve the ring-opening of 1,3-indanedione-based donor-acceptor cyclopropanes.
JOURNAL OF MOLECULAR LIQUIDS
(2023)
Article
Chemistry, Physical
Courtney A. DelPo, Saeed-Uz-Zaman Khan, Kyu Hyung Park, Bryan Kudisch, Barry P. Rand, Gregory D. Scholes
Summary: Enhanced delocalization is beneficial for absorbing molecules in organic solar cells, and polaritons offer exceptional delocalization that can improve the efficiency of bilayer organic photovoltaics by aiding in exciton delivery to the donor-acceptor interface. The decay of polaritons in bilayer cavities shows an additional pathway through charge transfer, indicating that the charge transfer from the polariton is fast enough to outcompete decay to the ground state.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2021)
Article
Chemistry, Organic
Gurupada Hazra, Sayantan Kundu, Rambabu Dandela, Barla Thirupathi
Summary: A facile synthetic approach for 6H-pyrrolo[3,2,1-de]acridines has been developed by using a cascade N-nucleophilic addition-cyclic Michael addition process. The reaction was conducted under metal-free conditions using arynes and indoles substituted with Michael acceptors. Additionally, photophysical studies showed that the newly synthesized pyrroloacridine compounds exhibited good fluorescence emission properties.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Dmytro I. Sierov, Illia V. Dzhulai, Kateryna I. Siryk, Kostiantyn V. Shvydenko, Tetiana I. Shvydenko, Kostiantyn Nazarenko, Aleksandr Kostyuk, Oleksandr S. Liashuk, Oleksandr O. Grygorenko
Summary: A systematic study on the SnAr reaction of halogenated fluoropyridines with (hetero)aliphatic nitrile anions was conducted, leading to the synthesis of functionalized pyridines bearing a (cyclo)alkyl or saturated heterocyclic substituent. The method demonstrated high chemo- and regioselectivity, as well as excellent scalability, and was applicable to various (hetero)aliphatic nitriles and isomeric halogenated 2- and 4-fluoropyridines. The synthesized products showed utility in additional functional group transformations, providing valuable pyridine-containing building blocks.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Matthew R. Lasky, Tolani K. Salvador, Sukrit Mukhopadhyay, Matthew S. Remy, Thomas P. Vaid, Melanie S. Sanford
Summary: This report describes the development of a photochemical method for C(sp(2))-H pyridination that leverages the photoexcitation of electron donor-acceptor (EDA) complexes. The reaction results in aryl radical cation intermediates that can be trapped with pyridine nucleophiles under aerobic conditions. This approach eliminates the need for an exogenous photocatalyst and is cost-effective.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Kathrin Bensberg, Kevin A. Kunz, Stefan F. Kirsch
Summary: In recent years, there has been increasing interest in developing synthetic methods for nitrogen-containing heterocycles. Tetrazoles, an important class of aromatic heterocycles, are particularly valuable in medicinal chemistry as bioisosteres. This study presents a simple method for accessing C-substituted tetrazoles through the thermolysis of geminal diazido malonamides. The formation and functionalization of in situ formed isocyanates and their corresponding reactions were also investigated.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Rahul Shukla, Anik Sen
Summary: Boron nitrides play a crucial role in various applications as lubricants and insulating agents. This study investigates the potential of B3N3 to act as both an electron acceptor and donor in noncovalent interactions, and computational simulations confirm the stability and governing mechanisms of these interactions.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2023)
Article
Chemistry, Organic
Hans-Ulrich Reissig, Fei Yu
Summary: In this study, the nucleophilic substitution of benzylic bromides with sodium azide and copper-catalyzed cycloaddition with terminal alkynes were combined to successfully synthesize complex alkynes bearing 1,2-oxazinyl substituents. The use of tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine (TBTA) as a ligand for the click step was found to be highly advantageous. However, the reductive cleavage of the 1,2-oxazine rings to aminopyran moieties did not proceed cleanly with these compounds.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Ryo Tsunokawa, Yukiko Karuo, Atsushi Tarui, Kazuyuki Sato, Takaaki Hosoya, Tomohiro Agou, Kentaro Kawai, Masaaki Omote
Summary: Metal-free pyridine arylations have been achieved using O-triflated pyridine N-oxides and N-alkylated indoles. The reactions proceed through reactive intermediates activated by Tf2O treatment, which allow for the selective installation of various indoles at the nitrogen-adjacent positions of pyridine. This protocol offers mild conditions, short reaction times, and ease of handling, making it an environmentally friendly approach to pyridine arylation.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Alexander A. Fadeev, Anton S. Makarov, Olga A. Ivanova, Maxim G. Uchuskin, Igor Trushkov
Summary: The divergent synthesis of benzannulated 2,8-dioxabicyclo[3.2.1]octanes and 2,3-dihydrobenzofurans using extended Corey-Chaykovsky reactions demonstrates the potential of this method in producing products with crucially different heterocyclic skeletons from the same starting compounds.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Review
Chemistry, Physical
Tatyana Shabatina, Olga Vernaya, Aleksei Shumilkin, Alexander Semenov, Mikhail Melnikov
Summary: The increasing appearance of antibiotic-resistant strains of microorganisms is a pressing modern problem. Nanoparticles offer a potential solution as new antibacterial agents, as they can target pathogenic microorganisms using mechanisms different from antibiotics. These particles possess a wide spectrum of antibacterial activity and can be conjugated with drugs for targeted delivery systems.
Article
Chemistry, Applied
Ivan A. Andreev, Maksim A. Boichenko, Nina K. Ratmanova, Olga A. Ivanova, Irina I. Levina, Victor N. Khrustalev, Igor A. Sedov, Igor Trushkov
Summary: A new method for the synthesis of 4-(dimethylamino)pyridinium azide was reported, which is a stable and non-explosive source of azide ion soluble in organic solvents. In protic ionic liquid media, this reagent serves as a safer alternative to toxic and unstable hydrazoic acid. The synthetic utility of this method was demonstrated using a model reaction, showing its wide range of applications.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Biochemistry & Molecular Biology
Maksim A. Boichenko, Andrey Yu. Plodukhin, Vitaly V. Shorokhov, Danyla S. Lebedev, Anastasya V. Filippova, Sergey S. Zhokhov, Elena A. Tarasenko, Victor B. Rybakov, Igor V. Trushkov, Olga A. Ivanova
Summary: We developed a straightforward synthetic route to important pyrrolidin-2-one compounds from donor-acceptor cyclopropanes. This method has a broad applicability, allowing the synthesis of compounds by using various amines and donor-acceptor cyclopropanes.
Article
Polymer Science
Ekaterina M. Zubanova, Tatiana A. Ivanova, Evgenii A. Ksendzov, Sergei Kostjuk, Peter S. Timashev, Mikhail Ya Melnikov, Elena N. Golubeva
Summary: This study investigated the coil-to-globule transition and dynamics of inhomogeneities in aqueous solutions of graft copolymers with different contents of oligolactide groups using EPR spectroscopy. It was found that an increase in oligolactide content leads to the formation of looser globules, allowing for the exchange of probe molecules between the globules and the external solution.
Article
Crystallography
Ekaterina M. Budynina, Sofiya I. Torgova, Artemiy Kuznetsov, Evgeniy P. Pozhidaev
Summary: The results of synthesizing and studying a new fluorinated achiral liquid crystal and its potential use as a matrix for ferroelectric liquid crystal mixtures are presented. The presence of a fluorine atom significantly influences the phase sequence, helix pitch, and tilt angle of the mixtures. The fluorinated matrix also leads to a decrease in spontaneous polarization and driving voltage of the electro-optical light shutters.
LIQUID CRYSTALS AND THEIR APPLICATION
(2022)
Article
Chemistry, Organic
Vitaly V. Shorokhov, Danila S. Lebedev, Maksim A. Boichenko, Sergey S. Zhokhov, Igor V. Trushkov, Olga A. Ivanova
Summary: A method for the synthesis of isoindoline derivatives was developed by using a domino reaction with a donor-acceptor cyclopropane and various primary amines. Under the hydrogenolysis conditions, the resulting N-benzyl-1,3-dihydroisoindole underwent selective cleavage of the exocyclic N-CH2Ar bond and followed by lactamization to form benzo[b]pyrrolizidinone. The same product can also be obtained by starting with reduction of the azidomethyl group at the ortho position of the donor aromatic substituent. Similarly, the generation of the o-2-aminoethyl group led to the formation of benzo[e]indolizidinone through two successive cyclization reactions.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS
(2023)
Article
Chemistry, Physical
Nina K. Ratmanova, Ivan A. Andreev, Vitaly A. Shcherbinin, Olga A. Ivanova, Irina I. Levina, Victor N. Khrustalev, Igor V. Trushkov
Summary: Triple-role thiocyanate-containing protic ionic liquids (PILs) were used as a regenerable solvent, a Bronsted acid catalyst, and a nucleophile source to achieve the ring-opening of 1,3-indanedione-based donor-acceptor cyclopropanes.
JOURNAL OF MOLECULAR LIQUIDS
(2023)
Review
Biochemistry & Molecular Biology
Tatyana I. Shabatina, Olga I. Vernaya, Mikhail Y. Melnikov
Summary: The appearance and increasing number of antibiotic-resistant microorganisms is a global problem. Nanoscale inorganic materials have the potential to combat this issue. This article discusses the mechanisms of microbial resistance to antibiotics, the actions of inorganic nanoparticles on bacterial cells, and the benefits of their combined use with antibacterial drugs. The prospects of using metal and metal oxide nanoparticles in targeted delivery systems for antibacterial compositions are also explored.
Review
Pharmacology & Pharmacy
Tatyana I. Shabatina, Olga I. Vernaya, Nikolay L. Shimanovskiy, Mikhail Ya. Melnikov
Summary: The development of antiviral treatment and anticancer theragnostic agents in recent decades has been closely associated with nanotechnologies, especially inorganic nanoparticles (INPs) made of metal and metal oxides. INPs, with their large specific surface area and high activity, can be easily functionalized for various applications such as targeted drug delivery, magnetic hyperthermia, and plasmonic photothermal therapies. The magnetic properties of iron oxide and ferrite nanoparticles make them ideal for magnetic resonance imaging and targeted cancer therapy. Moreover, gold and silver nanoparticles show promise in plasmonic photothermal and antiviral therapies, respectively.
Article
Chemistry, Organic
Olga A. A. Ivanova, Vitaly V. V. Shorokhov, Ivan A. A. Andreev, Nina K. K. Ratmanova, Victor B. B. Rybakov, Elena D. D. Strel'tsova, Igor V. V. Trushkov
Summary: A donor-acceptor cyclopropane, derived from 1,3-indanedione and bearing an ortho-ethoxymethyl-protected phenolic group at the donor aryl substituent, was synthesized through a reaction sequence involving Knoevenagel condensation and Corey-Chaykovsky cyclopropanation. The structure of the synthesized cyclopropane was confirmed by single-crystal X-ray diffraction analysis.
Article
Chemistry, Organic
Vitaly V. Shorokhov, Sergey S. Zhokhov, Victor B. Rybakov, Maksim A. Boichenko, Ivan A. Andreev, Nina K. Ratmanova, Igor V. Trushkov, Olga A. Ivanova
Summary: A Lewis acid-promoted domino ring-opening cyclization of readily available donor-acceptor cyclopropanes with a preinstalled electrophilic center, embedded in a donor group, to functionalized 1,2-dihydronaphthalenes is reported. The obtained compounds are transformed to pharmacologically attractive bridged tricyclic esters in a diastereospecific manner.
Article
Chemistry, Organic
Anna E. Vartanova, Irina I. Levina, Nina K. Ratmanova, Ivan A. Andreev, Olga A. Ivanova, Igor Trushkov
Summary: This study investigated the Lewis acid-catalysed reactions of donor-acceptor cyclopropanes with 1,3-disubstituted 5-aminopyrazoles. It was found that under the catalysis of gallium(iii) chloride, the nucleophilic attack of the exocyclic amino group led to the chemoselective three-membered ring opening. On the other hand, in the presence of scandium(iii) triflate, N-alkylation, C(4)-alkylation, or a mixture of both reactions occurred. The C(4)-alkylation products were further transformed into tetrahydropyrazolo[3,4-b]azepines, which have potential applications in medicinal chemistry and pharmacology.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)