Publications
2024
Reversible pH-dependent cyclization of hydroxy-substituted gem-chloronitroso compounds to isoxazoline N-oxides and 5,6-dihydro-4H-1,2-oxazine N-oxides
Roman S. Malykhin, Alexey Yu. Sukhorukov
Russ. Chem. Bull. 2024, 73,1303. doi: 10.1007/s11172-024-4247-1
3-Halo-5,6-dihydro-4H-1,2-oxazine N-oxides as synthetic equivalents of unsaturated nitrile oxides in the [3 + 2]-cycloaddition with arynes: synthesis of substituted 3-vinyl-1,2-benzisoxazoles
Alexander A. Lukoyanov, Svetlana A. Aksenova, Andrey A. Tabolin, Alexey Yu. Sukhorukov
Org. Biomol. Chem. 2024, 22, 3615. doi: 10.1039/D4OB00391H
An Intramolecular Nitroso-Meerwein-Ponndorf-Verley-Oppenauer Reaction to Access Fused Pyrrolidine Scaffolds
Roman S. Malykhin, Svetlana A. Aksenova, Alexey Yu. Sukhorukov
Org. Lett. 2024, 26, 450. doi: 10.1021/acs.orglett.3c03552
Catalytic Reductive Recyclization of Functionalized Isoxazoline N-Oxides to Pyrrolizidine-3-ones
Ilya V. Okladnikov, Svetlana A. Aksenova, Sema L. Ioffe, Alexey Yu. Sukhorukov
J. Org. Chem. 2024, 89, 379. doi: 10.1021/acs.joc.3c02154
Divergent synthesis of nitrocyclopropanes and isoxazoline N-oxides from nitro compounds and vinyl sulfonium salts
Pavel Yu. Ushakov, Ivan S. Golovanov, Sema L. Ioffe, Andrey A. Tabolin
Org. Chem. Front. 2024, 11, 315. doi: 10.1039/D3QO01664A
2023
Crown-hydroxylamines are pH-dependent chelating N,O-ligands with a potential for aerobic oxidation catalysis
Vladislav K. Lesnikov, Ivan S. Golovanov, Yulia V. Nelyubina, Svetlana A. Aksenova, Alexey Yu. Sukhorukov
Nature Commun., 2023, 14, 7673. doi: 10.1038/s41467-023-43530-6
The Reduction of Carbonyl Compounds with Dicyclopentylzinc: A New Example of Asymmetric Amplifying Autocatalysis
Elena Sh. Saigitbatalova, Liliya Z. Latypova, Almaz A. Zagidullin, Almira R. Kurbangalieva, Ilya D. Gridnev
Int. J. Mol. Sci. 2023, 24(23), 17048. doi: 10.3390/ijms242317048
Nickel-Catalyzed Asymmetric Hydrogenation of α-Substituted Vinylphosphonates and Diarylvinylphosphine Oxides
Hanlin Wei, Hao Chen, Dr. Jianzhong Chen, Ilya D. Gridnev, Wanbin Zhang
Angew. Chem. Int. Ed., 2023, 62, e202214990. doi: 10.1002/anie.202214990
Co-Catalyzed Asymmetric Hydrogenation. The Same Enantioselection Pattern for Different Mechanisms
Ilya D. Gridnev
Int. J. Mol. Sci. 2023, 24(6), 5568. doi: 10.3390/ijms24065568
Development of Novel Indole and Coumarin Derivatives as Antibacterial Agents That Target Histidine Kinase in S. aureus
Lisha K. Poonacha, Rashmi Ramesh, Akshay Ravish, Arunkumar Mohan, Pradeep M. Uppar, Prashant K. Metri, Nanjunda Swamy Shivananju, Santosh L. Gaonkar, Shubha Gopal, Alexey Yu Sukhorukov, Vijay Pandey, Priya Babu Shubha, Basappa Basappa
Appl. Microbiol. 2023, 3(4), 1214. doi: 10.3390/applmicrobiol3040084
Reaction of Triazolic Aldehydes with Diisopropyl Zinc: Chirality Dissipation versus Amplification
Oleg A. Mikhaylov, Elena Sh. Saigitbatalova, Liliya Z. Latypova, Almira R. Kurbangalieva, Ilya D. Gridnev
Symmetry 2023, 15(7), 1382. doi: 10.3390/sym15071382
Reductive Denitrogenation of Six-membered Cyclic Nitronates to Densely Substituted Dihydrofurans with Raney® Nickel/AcOH System
Evgeny V. Pospelov, Alexander V. Zhirov, Baglan Kamidolla, Alexey Yu. Sukhorukov
Adv. Synth. Catal., 2023, 365, 2850. doi: 10.1002/adsc.202300573
Chapter Four - Fluoroheterocycle formation using fluoroalkynes and their synthetic equivalents
Andrey A. Tabolin
Advances in Heterocyclic Chemistry, 2023, 140, 125. doi: 10.1016/bs.aihch.2022.11.002
[3+3]-Annulation of Cyclic Nitronates with Vinyl Diazoacetates: Diastereoselective Synthesis of Partially Saturated [1,2]Oxazino[2,3-b][1,2]oxazines and Their Base-Promoted Ring Contraction to Pyrrolo[1,2-b][1,2]oxazine Derivatives
Yulia A. Antonova, Yulia V. Nelyubina, Sema L. Ioffe, Andrey A. Tabolin
Molecules, 2023, 28(7), 3025. doi: 10.3390/molecules28073025
Building Up a Piperazine Ring from a Primary Amino Group via Catalytic Reductive Cyclization of Dioximes
Evgeny V. Pospelov, Alexey Yu. Sukhorukov
Int. J. Mol. Sci., 2023, 24(14), 11794. doi: 10.3390/ijms241411794
Enhanced photostability of multication lead halide perovskites through the use of azaadamantane-based modifiers
V.V. Ozerova, N.A. Emelianov, L.G. Gutsev, D.V. Korchagin, G.V. Shilov, N.N. Dremova,
B.R. Ramachandran, A.Y. Sukhorukov, S.M. Aldoshin, L.A. Frolova, P.A. Troshin
Materials Today Chemistry. 2023, 30, 101590. doi: 10.1016/j.mtchem.2023.101590

Michael addition of P-nucleophiles to azoalkenes provides simple access to phosphine oxides bearing an alkylhydrazone moiety

Alexandr O. Kokuev, Alexey Yu. Sukhorukov
Front. Chem. 2023, 11, 1177680. doi: 10.3389/fchem.2023.1177680
Nitronate-aryne cycloaddition as a concise route to stereochemically complex fused benzisoxazolines and amino alcohols
Aleksander A. Lykoyanov, Andrey A. Tabolin, Yulia V. Nelyubina, Svetlana A. Aksenova, Alexey Yu. Sukhorukov
Org. Biomol. Chem., 2023, 21, 3871. doi: 10.1039/D3OB00235G
Global Search for Stable C4H5NO Compounds—Guinness Molecules and Stability Islands
Oleg A. Mikhaylov, Ilya D. Gridnev
Molecules, 2023, 28(2), 728. doi: 10.3390/molecules28020728
Interrupted Nef and Meyer Reactions: A Growing Point for Diversity-Oriented Synthesis Based on Nitro Compounds
Alexey Yu. Sukhorukov
Molecules, 2023, 28(2), 686. doi: 10.3390/molecules28020686
2022
Interrupted Nef Reaction of Cyclic Nitronates: Diastereoselective Access to Densely Substituted α-Chloronitroso Compounds
Roman S. Malykhin, Yaroslav D. Boyko, Yulia V. Nelyubina, Sema L. Ioffe, Alexey Yu. Sukhorukov
J. Org. Chem., 2022, 87, 16617–16631. doi: 10.1021/acs.joc.2c02281
Small D-π-A-π-D organic dyes for near-infrared emitting OLEDs with excellent external quantum efficiency
Vladislav M.Korshunov, Timofey N. Chmovzh, Alexandra Ya Freidzon, Mikhail E. Minyaev, Artem D. Barkanov, Ivan S. Golovanov, Lyudmila V. Mikhalchenko, Igor C. Avetisov, Ilya V. Taydakov, Oleg A. Rakitin
Dyes and Pigments, 2022, 208, 110860. doi: 10.1016/j.dyepig.2022.110860
1,4,6,10-Tetraazaadamantanes (TAADs) with N-amino groups: synthesis and formation of boron chelates and host–guest complexes
Artem N. Semakin, Ivan S. Golovanov , Yulia V. Nelyubina, Alexey Yu. Sukhorukov
Beilstein J. Org. Chem., 2022, 18, 1424–1434. doi: 10.3762/bjoc.18.148
Iron(IV) complexes with tetraazaadamantane-based ligands: synthesis, structure, applications in dioxygen activation and labeling of biomolecules
Ivan S. Golovanov, Anton V. Leonov, Vladislav K. Lesnikov, Evgeny V. Pospelov, Kirill V. Frolov, Alexander A. Korlyukov, Yulia V. Nelyubina, Valentin V. NovikovAlexey Yu. Sukhorukov 
Dalton Trans., 2022, 51, 4284-4296. doi: 10.1039/D1DT04104E
Tandem Michael addition/elimination – novel reactivity of pyridinium ylides in reaction with electron-deficient alkenes
Alexei N. Izmest'ev, Vladimir A. Motornov, Dmitry B. Vinogradov, Sema L. Ioffe,  Angelina N. Kravchenko, Galina A. Gazieva 
Org. Chem. Front., 2022, 9, 4998 - 5004. doi: 10.1039/D2QO00911K
Nickel-catalysed asymmetric hydrogenation of oximes
Bowen Li, Jianzhong Chen, Dan Liu, Ilya D. Gridnev, Wanbin Zhang
Nature Chemistry, 2022, 14, 920 - 927. doi: 10.1038/s41557-022-00971-8
London Disperse Interactions Assist Chiral Induction in the Soai Autoamplifying Reaction Provoked by 1- and 2-Aza[6]helicenes
Roman V. Zonov, Ilya D. Gridnev
Catalysts, 2022, 12(8), 859. doi: 10.3390/catal12080859
γ-Pyronecarbaldehyde-Based Practical Asymmetric Catalytic Synthesis of Chiral 2,4-Dihydroxycarboxylic Acids and α-Hydroxy-γ-lactones
Maxim V. Smirnov, Alexander S. Kucherenko, Ilya D. Gridnev, Alexander A. Korlyukov, Sergei G. Zlotin
Adv. Synth. Catal., 2022, 364, 3245. doi: 10.1002/adsc.202200859
Synthesis of 3-Haloisoxazolines by Deoxygenation of 3-Haloisoxazoline N-Oxides under Treatment with Acetyl Bromide
Anastasia A. Fadeeva, Sema L. Ioffe, Andrey A. Tabolin
ChemistrySelect, 2022, 7, e202202267. doi: 10.1002/slct.202202267
Ring Closure of Nitroalkylmalonates for the Synthesis of Isoxazolines under the Acylation Conditions
Yulia A. Antonova, Yulia V. Nelyubina, Sema L. Ioffe, Alexey Yu. Sukhorukov, Andrey A. Tabolin
Adv. Synth. Catal., 2022, 364, 2606. doi: 10.1002/adsc.202200420
Deoxygenative Arylation of 5,6-Dihydro-4H-1,2-oxazine-N-oxides with Arynes
Alexander A. Lukoyanov, Andrey A. Tabolin, Yulia V. Nelyubina, Sema L. Ioffe, Alexey Yu. Sukhorukov
J. Org. Chem., 2022, 87, 6838 – 6851. doi: 10.1021/acs.joc.2c00515
Tandem [3+2]-cycloaddition/homo-Baldwin rearrangement of silyl nitronates and donor-acceptor cyclopropenes. A novel approach to polysubstituted aziridines starting from nitro compounds
Yana I.Lichtenstein, Ivan S.Golovanov, Sema L.Ioffe, Andrey A.Tabolin
Tetrahedron, 2022, 110, 132693. doi: 10.1016/j.tet.2022.132693
Oxidative [3+2]-annulation of nitroalkenes and azolium ylides in the presence of Cu(II): efficient synthesis of [5,5]-annulated N-fused heterocycles
Vladimir A. Motornov, Andrey A. Tabolin, Sema L. Ioffe
New J. Chem., 2022, 46, 4134-4141. doi: 10.1039/D1NJ05332A
Piperazine-1,4-diol (PipzDiol): synthesis, stereodynamics and assembly of supramolecular hydrogen-bonded 2D networks
Vladislav K. Lesnikov, Yulia V. Nelyubina, Alexey Yu. Sukhorukov
New J. Chem., 2022, 46, 20386-20394. doi: 10.1039/D2NJ03012H
Asymmetric Synthesis of a Pyrrolizidinone-Based hNK1 Antagonist through Reductive Ring Contraction of a Six-Membered Cyclic Nitronate
Ilya V. Okladnikov, Yaroslav D. Boyko, Yulia V. Nelyubina, Sema L. Ioffe, Alexey Yu. Sukhorukov
Eur. J. Org. Chem., 2022, e20220079. doi: 10.1002/ejoc.202200796
Regio- and diastereoselective access to densely functionalized ketones via the Boekelheide rearrangement of isoxazoline N-oxides
Pavel Yu. Ushakov,  Sema L. Ioffe,  Alexey Yu. Sukhorukov
Org. Biomol. Chem., 2022, 20, 5624 - 5637. doi: 10.1039/D2OB00787H
Synthesis of Bis(β-Oximinoalkyl)malonates and Their Catalytic Reductive Cyclization to Piperidines
Evgeny V. Pospelov,  Yaroslav D. Boyko,  Sema L. Ioffe,  Alexey Yu. Sukhorukov
Adv. Synth. Catal., 2022, 364, 2557. doi: 10.1002/adsc.202200424
Transition metal atoms grafted on the nanodiamonds surface: Identification and guest – host spin – spin interactions
Ilya D. Gridnev
Mend. Commun., 2022, 32, 2, 143 - 151. doi: 10.1016/j.mencom.2022.03.001
Birds of a Feather — Asymmetric Organocatalysis Meets Asymmetric Transition Metal Catalysis
Ilya D. Gridnev
Catalyst, 2022, 12(2), 214. doi: 10.3390/catal12020214
Recent advances in the application of ylide-like species in [4 + 1]-annulation reactions: an updated review
Pavel Yu. Ushakov, Sema L. Ioffe, Alexey Yu.Sukhorukov
Org. Chem. Front., 2022, 9, 5358 - 5382. doi: 10.1039/D2QO00698G
2021
Addition of malonic esters to azoalkenes generated in situ from α-bromo- and α-chlorohydrazones
Aleksandr O.Kokuev, Sema L.Ioffe, Alexey Yu.Sukhorukov
Tetrahedron Lett., 2021, 83, 153414. doi: 10.1016/j.tetlet.2021.153414
Copper-Mediated Oxidative [3+2]-Annulation of Nitroalkenes and Ylides of 1,2-Diazines: Assembly of Functionalized Pyrrolo[1,2-b]pyridazines
Vladimir A. Motornov, Andrey A. Tabolin, Valentine G. Nenajdenko, Sema L. Ioffe
ChemistrySelect, 2021, 6, 9969. doi: 10.1002/slct.202103189
Construction of Saturated Oxazolo[3,2-b][1,2]oxazines via Tandem [3+2]-cycloaddition/[1,3]-Rearragement of Cyclic Nitronates and Ketenes
Roman S. Malykhin, Ivan S. Golovanov, Yulia V. Nelybina, Sema L. Ioffe and Alexey Yu. Sukhorukov
J. Org. Chem., 2021, 86, 16337–16348. doi: 10.1021/acs.joc.1c01744
Sequential Acylation/Silylation/Hetero-Claisen Rearrangement of Nitroalkanes for the Synthesis of Protected Hydroxyoxime Derivatives
Yulia A. Antonova, Prof. Dr. Sema L. Ioffe, Prof. Dr. Alexey Yu. Sukhorukov, Dr. Andrey A. Tabolin
Eur. J. Org. Chem., 2021, 2021, 3197. doi: 10.1002/ejoc.202100469
Dehydration of isoxazoline N-oxides under electrophilic conditions – An alternative approach toward 3-haloisoxazoles
Anastasia A. Fadeeva, Prof. Dr. Sema L. Ioffe, Dr. Andrey A. Tabolin
Tetrahedron Lett., 2021, 73, 153106. doi: 10.1016/j.tetlet.2021.153106
Sequential Formal [4+1]Cycloaddition, C−H Functionalization and Suzuki–Miyaura Cross‐Coupling for the Synthesis of Trisubstituted Isoxazolines
Pavel Yu. Ushakov, Prof. Dr. Alexey Yu. Sukhorukov, Prof. Dr. Sema L. Ioffe, Dr. Andrey A. Tabolin
Eur. J. Org. Chem., 2021, 2021, 2680. doi: 10.1002/ejoc.202100313
Spectacular Enhancement of the Thermal and Photochemical Stability of MAPbI3 Perovskite Films Using Functionalized Tetraazaadamantane as a Molecular Modifier
Victoria V. Ozerova, Ivan S. Zhidkov, Aleksandra Boldyreva, Nadezhda N. Dremova, Nikita A. Emelianov, Gennady V. Shilov, Lyubov A. Frolova, Ernst Z. Kurmaev, Alexey Y. Sukhorukov, Sergey M. Aldoshin,  Pavel A. Troshin
Energies, 202114, 3, 669. doi: 10.3390/en14030669
Revealing the Structure of Transition Metal Complexes of Formaldoxime
Ivan S. Golovanov, Roman S. Malykhin, Vladislav K. Lesnikov, Yulia V. Nelyubina, Valentin V. Novikov, Kirill V. Frolov, Andrey I. Stadnichenko, Evgeny V. Tretyakov, Sema L. Ioffe, and Alexey Yu. Sukhorukov
Inorg. Chem., 2021, 60, 8, 5523–5537. doi: 10.1021/acs.inorgchem.0c03362
Merging Boron with Nitrogen–Oxygen Bonds: A Review on BON Heterocycles
Ivan S. Golovanov, Alexey Yu. Sukhorukov
Top. Curr. Chem., 2021, 8, 379. doi: 10.1007/s41061-020-00317-3
Copper-catalyzed [3 + 2]-cycloaddition of α-halonitroalkenes with azomethine ylides: facile synthesis of multisubstituted pyrrolidines and pyrroles
Vladimir A. Motornov, Andrey A. Tabolin, Yulia V. Nelyubina, Valentine G. Nenajdenko, Sema L. Ioffe 
Org. Biomol. Chem., 2021,19, 3413-3427. doi: 10.1039/D1OB00146A
2020
Recent Advances in the Stereoselective Synthesis of Pyrrolizidin‐3‐ones
Alexey Yu. Sukhorukov
Synthetic Approaches to Nonaromatic Nitrogen Heterocycles, Ch. 8. 2020, Wiley: Hoboken, pp. 179-223. doi: 10.1002/9781119708841.ch8
2,4,9‐Triazaadamantanes with “Clickable” Groups: Synthesis, Structure and Applications as Tripodal Platforms
Artem n. Semakin, Yulia V. Nelyubina, Sema L. Ioffe and Alexey Yu. Sukhorukov
Eur. J. Org. Chem., 2020, 43, 17, 6723-6735. doi: 10.1002/ejoc.202000832
Asymmetric Synthesis of Merck’s Potent hNK1 Antagonist and Its Stereoisomers via Tandem Acylation/[3,3]-Rearrangement of 1,2-Oxazine N-Oxides
Valentine S. Dorokhov, Yulia V. Nelyubina, Sema L. Ioffe and Alexey Yu. Sukhorukov
J. Org. Chem., 2020, 85, 17, 11060-11071. doi: 10.1021/acs.joc.0c01322
Acid‐Mediated Three Component Assembly of 4‐Fluoropyrazoles from α‐Fluoronitroalkenes, Hydrazines, and Aldehydes
Vladimir A. Motornov, Andrey A. Tabolin, Yulia V. Nelyubina, Valentine G. Nenajdenko and Sema L. Ioffe
Eur. J. Org. Chem., 2020, 2020, 32, 5211-5219. doi: 10.1002/ejoc.202000841
Chlorination of Conjugated Nitroalkenes with PhICl2 and SO2Cl2 for the Synthesis of α-Chloronitroalkenes
Anastasia A. Fadeeva, Sema L. Ioffe and Andrey A. Tabolin
Synthesis, 2020, 52(18), 2769-2688. doi: 10.1055/s-0040-1707396
The Cyclic Nitronate Route to Pharmaceutical Molecules: Synthesis of GSK’s Potent PDE4 Inhibitor as a Case Study
Evgeny V. Pospelov, Ivan S. Golovanov, Sema L. Ioffe and Alexey Yu. Sukhorukov
Molecules2020, 25(16), 3613. doi: 10.3390/molecules25163613

Nitro Compounds as Versatile Building Blocks for the Synthesis of Pharmaceutically Relevant Substances

Alexey Yu. Sukhorukov
Frontiers in Chemistry, 2020, Volume 8, 918 . doi: 10.3389/fchem.2020.595246
Catalytic Reductive Amination of Aldehydes and Ketones With Nitro Compounds: New Light on an Old Reaction
Alexey Yu. Sukhorukov
Frontiers in Chemistry, 2020, Volume 8, 215 . doi: 10.3389/fchem.2020.00215
Identification of a novel 1,2 oxazine that can induce apoptosis by targeting NF-κB in hepatocellular carcinoma cells
Chaithanya Somua, Chakrabhavi Dhananjaya Mohan, Sachin Ambekar, Dukanya, Shobith Rangappa, CP Baburajeev, Alexey Sukhorukov, Srishti Mishra, Muthu K Shanmugam, Arunachalam Chinnathambi, Tahani Awad Alahmadi, Sulaiman Ali Alharbi, Basappa, Kanchugarakoppal S.Rangappa
Biotechnology Reports, 2020, Volume 25, e00438. doi: 10.1016/j.btre.2020.e00438
Copper-mediated oxidative [3 + 2]-annulation of nitroalkenes and pyridinium imines: efficient synthesis of 3-fluoro- and 3-nitro-pyrazolo[1,5-a]pyridines
Vladimir A. Motornov, Andrey A. Tabolin, Yulia V. Nelyubina, Valentine G. Nenajdenko and Sema L. Ioffe
Org. Biomol. Chem. 2020,18, 1436-1448. doi: 10.1039/C9OB02668A
Umpolung of Enamines: An Overview on Strategies and Synthons
Alexey Yu. Sukhorukov
Synlett, 2020; 31(05), 439-449. doi: 10.1055/s-0037-1610741
C−H Reactivity of the α‐Position in Nitrones and Nitronates
Alexey Yu. Sukhorukov
Adv. Synth. Catal. 2020, 362, 724. doi: 10.1002/adsc.201900718
2019
Synthesis of Isoxazolines from Nitroalkanes via a [4+1]‐Annulation Strategy
Pavel Yu. Ushakov, Elizaveta A. Khatuntseva, Yulia V. Nelyubina, Andrey A. Tabolin, Sema L. Ioffe, Alexey Yu. Sukhorukov
Adv. Synth. Catal. 2019, 361, 5322. doi: 10.1002/adsc.201901000
Nucleophilic Halogenation of Cyclic Nitronates: A General Access to 3-Halo-1,2-Oxazines
Roman S. Malykhin, Aleksandr O. Kokuev, Valentin S. Dorokhov, Yulia V. Nelyubina, Vladimir A. Tartakovsky, Andrey A. Tabolin, Sema L. Ioffe, Alexey Yu. Sukhorukov
J. Org. Chem. 2019, 84, 21, 13794-13806. doi: 10.1021/acs.joc.9b02010
Tandem double acylation/[3,3]-rearrangement of aliphatic nitro compounds: a route to α-oxygenated oxime derivatives
Antonova, Y. A.; Nelyubina, Y. V.; Sukhorukov, A. Y.; Ioffe, S. L.; Tabolin, A. A.
Org. Biomol. Chem. 2019, 17, 5997-6006. doi: 10.1039/C9OB01005J
Michael Addition of P-Nucleophiles to Conjugated Nitrosoalkenes
Naumovich, Y. A.; Ioffe, S. L.; Sukhorukov, A. Y.
J. Org. Chem. 2019, 84, 11, 7244–7254. doi: 10.1021/acs.joc.9b00924
Tandem Deoxygenation/Halogenation of N‐Oxides Under Acylation Conditions: Scope and In Situ IR Spectroscopic Study
Malykhin, R. S.; Golovanov, I. S.; Ioffe, S. L.; Sukhorukov, A. Y.
Eur. J. Org. Chem.
2019, 4139–4148. doi: 10.1002/ejoc.201900131
In Situ Generated Magnesium Cyanide as an Efficient Reagent for Nucleophilic Cyanation of Nitrosoalkenes and Parent Nitronates
Ushakov, P. Y.; Tabolin, A. A.; Ioffe, S. L.; Sukhorukov, A. Y.
Eur. J. Org. Chem.
2019, 1888–1892. doi: 10.1002/ejoc.201801761
Copper-mediated oxidative [3 + 2]-annulation of nitroalkenes and pyridinium ylides: general access to functionalized indolizines and efficient synthesis of 1-fluoroindolizines
Motornov, V. A.; Tabolin, A. A.; Nelyubina, Y. V; Nenajdenko, V. G.; Ioffe, S. L.
Org. Biomol. Chem.
2019, 17 (6), 1442–1454. doi: 10.1039/C8OB03126F
2018
A New Algorithm for the Reactivity Umpolung of Aliphatic Nitro Compounds
Ioffe, S. L.; Khoroshutina, Y. A.; Smirnov, V. O.; Mikhaylov, A. A.
Kinet. Catal.
2018, 59 (6), 691–700. doi: 10.1134/S002315841806006X
α-Electrophilic Reactivity of Nitronates
Tabolin, A. A.; Sukhorukov, A. Y.; Ioffe, S. L.
Chem. Rec.
2018, 18 (10), 1489–1500. doi: 10.1002/tcr.201800009
Acylation of Nitronates: [3,3]-Sigmatropic Rearrangement of in Situ Generated N-Acyloxy, N-oxyenamines
Kokuev, A. O.; Antonova, Y. A.; Dorokhov, V. S.; Golovanov, I. S.; Nelyubina, Y. V.;
Tabolin, A. A.; Sukhorukov, A. Y.; Ioffe, S. L.
J. Org. Chem.
2018, 83 (18), 11057–11066. doi: 10.1021/acs.joc.8b01652
Fluoronitroalkenes in tandem [4 + 1]/[3 + 2]-cycloaddition: One-pot three-component assembly of fluorinated bicyclic nitroso acetals
Motornov, V. A.; Tabolin, A. A.; Novikov, R. A.; Nelyubina, Y. V.;
Nenajdenko, V. G.; Ioffe, S. L.
Org. Chem. Front.
2018, 5 (17), 2593–2599. doi: 10.1039/c8qo00623g
Exploiting Coupling of Boronic Acids with Triols for a pH-Dependent "Click-Declick" Chemistry
Golovanov, I. S.; Mazeina, G. S.; Nelyubina, Y. V.; Novikov, R. A.; Mazur, A. S.; Britvin, S. N.; Tartakovsky, V. A.; Ioffe, S. L.; Sukhorukov, A. Y.
J. Org. Chem. 2018, 83 (17), 9756–9773. doi: 10.1021/acs.joc.8b01296
Synthesis of unsaturated silyl nitronates via the silylation of conjugated nitroalkenes
Khotyantseva, E. A.; Tabolin, A. A.; Novikov, R. A.; Nelyubina, Y. V.; Ioffe, S. L.
Tetrahedron Lett. 2018, 59 (32), 3128–3131. doi: 10.1016/j.tetlet.2018.07.011
Green, Catalyst-Free Reaction of Indoles with β-Fluoro-β-nitrostyrenes in Water
Aldoshin, A. S.; Tabolin, A. A.; Ioffe, S. L.; Nenajdenko, V. G.
European J. Org. Chem. 2018, 3816–3825. doi: 10.1002/ejoc.201800385
Synthesis of 2,5-diaryl-4-halo-1,2,3-triazoles and comparative study of their fluorescent properties
Motornov, V. A.; Tabolin, A. A.; Novikov, R. A.; Shepel, N. E.; Nenajdenko, V. G.; Ioffe, S. L.
Tetrahedron 2018, 74 (28), 3897–3903. doi: 10.1016/j.tet.2018.05.071
Synthesis of α-Thiooximes by Addition of Thiols to N, N-Bis(oxy)-enamines: A Comparative Study of S-, N-, and O-Nucleophiles in Michael Reaction with Nitrosoalkene Species
Naumovich, Y. A.; Kokuev, A. O.; Sukhorukov, A. Y.; Ioffe, S. L.
Synlett 2018, 29 (10), 1334–1339. doi: 10.1055/s-0036-1591973
Diastereoselective synthesis and profiling of bicyclic imidazolidinone derivatives bearing a difluoromethylated catechol unit as potent phosphodiesterase 4 inhibitors
Dorokhov, V. S.; Golovanov, I. S.; Tartakovsky, V. A.; Sukhorukov, A. Y.; Ioffe, S. L.
Org. Biomol. Chem. 2018, 16, 6900–6908. doi: 10.1039/C8OB01039K
A Novel Entry to 3,4,5-Trisubstituted 2-Pyrrolidones from Isoxazoline-N-oxides
Zhmurov, P. A.; Ushakov, P. Y.; Novikov, R. A.; Sukhorukov, A. Y.; Ioffe, S. L.
Synlett
2018, 29 (14), 1871–1874. doi: 10.1055/s-0037-1610213
2017
Synthesis and Regioselective N-2 Functionalization of 4-Fluoro-5-aryl-1,2,3-NH-triazoles
Motornov, V. A.; Tabolin, A. A.; Novikov, R. A.; Nelyubina, Y. V.; Ioffe, S. L.; Smolyar, I. V.; Nenajdenko, V. G.
European J. Org. Chem. 2017, 2017 (46), 6851–6860. doi: 10.1002/ejoc.201701338
Addition of HO-Acids to N,N-Bis(oxy)enamines: Mechanism, Scope and Application to the Synthesis of Pharmaceuticals
Naumovich, Y. A.; Golovanov, I. S.; Sukhorukov, A. Y.; Ioffe, S. L.
European J. Org. Chem.
2017, 2017 (41), 6209–6227. doi: 10.1002/ejoc.201701266
Conjugated nitrosoalkenes as Michael acceptors in carbon-carbon bond forming reactions: A review and perspective
Boyko, Y. D.; Dorokhov, V. S.; Sukhorukov, A. Y.; Ioffe, S. L.
Beilstein J. Org. Chem.
2017, 13, 2214–2234. doi: 10.3762/bjoc.13.220
Synthesis and Structure of N,N-Dinitroamidoborane Complexes
Shitov, O. P.; Tartakovsky, V. A.; Golovanov, I. S.; Sukhorukov, A. Y.; Ioffe, S. L.
Chem. - An Asian J.
2017, 12 (17), 2237–2244. doi: 10.1002/asia.201700603
Organic and hybrid systems: from science to practice
Ananikov, V. P.; Eremin, D. B.; Yakukhnov, S. A.; Dilman, A. D.; Levin, V. V.; Egorov, M. P.; Karlov, S. S.; Kustov, L. M.; Tarasov, A. L.; Greish, A. A.; Shesterkina, A. A.; Sakharov, A. M.; Nysenko, Z. N.; Sheremetev, A. B.; Stakheev, A. Y.; Mashkovsky, I. S.;
Sukhorukov, A. Y.; Ioffe, S. L.; Terent'ev, A. O.; Vil, V. A.; Tomilov, Y. V.; Novikov, R. A.;
Zlotin, S. G.; Kucherenko, A. S.; Ustyuzhanina, N. E.; Krylov, V. B.; Tsvetkov, Y. E.;
Gening, M. L.; Nifantiev, N. E.
Mendeleev Commun.
2017, 27 (5), 425–438. doi: 10.1016/j.mencom.2017.09.001
Recent Advances in the Synthesis and Chemistry of Nitronates
Tabolin, A. A.; Sukhorukov, A. Y.; Ioffe, S. L.; Dilman, A. D.
Synth.
2017, 49 (15), 3255–3268. doi: 10.1055/s-0036-1589063
Radical Nitration-Debromination of α-Bromo-α-fluoroalkenes as a Stereoselective Route to Aromatic α-Fluoronitroalkenes - Functionalized Fluorinated Building Blocks for Organic Synthesis
Motornov, V. A.; Muzalevskiy, V. M.; Tabolin, A. A.; Novikov, R. A.; Nelyubina, Y. V.; Nenajdenko, V. G.; Ioffe, S. L.
J. Org. Chem.
2017, 82 (10), 5274–5284. doi: 10.1021/acs.joc.7b00578
Divergent Reactivity of In Situ Generated Metal Azides: Reaction with N,N-Bis(oxy)enamines as a Case Study
Zhmurov, P. A.; Khoroshutina, Y. A.; Novikov, R. A.; Golovanov, I. S.; Sukhorukov, A. Y.; Ioffe, S. L.
Chem. - A Eur. J.
2017, 23 (19), 4570–4578. doi: 10.1002/chem.201605390
2016
Construction of bis-, tris- and tetrahydrazones by addition of azoalkenes to amines and ammonia
Semakin, A. N.; Kokuev, A. O.; Nelyubina, Y. V.; Sukhorukov, A. Y.; Zhmurov, P. A.;
Ioffe, S. L.; Tartakovsky, V. A.
Beilstein J. Org. Chem.
2016, 12, 2471–2477. doi: 10.3762/bjoc.12.241
Synthesis of 1,4,6,10-tetraazaadamantane quaternary derivatives
Semakin, A. N.; Golovanov, I. S.; Sukhorukov, A. Y.; Ioffe, S. L.; Tartakovsky, V. A.
Russ. Chem. Bull.
2016, 65 (9), 2270–2277. doi: 10.1007/s11172-016-1577-7
Synthesis and chemical transformations of six/six-membered bicyclic nitroso acetals
Tabolin, A. A.; Gorbacheva, E. O.; Novikov, R. A.; Khoroshutina, Y. A.;
Nelyubina, Y. V.; Ioffe, S. L.
Russ. Chem. Bull.
2016, 65 (9), 2243–2259. doi: 10.1007/s11172-016-1575-9
Small Ring Compounds and N-oxides: Cycloadditions and Related Processes
Tabolin, A. A.; Ioffe, S. L.
Isr. J. Chem.
2016, 56 (6–7), 385–398. doi: 10.1002/ijch.201500082
Metal-assisted addition of a nitrate anion to bis(oxy)enamines. A general approach to the synthesis of α-nitroxy-oxime derivatives from nitronates
Naumovich, Y. A.; Buckland, V. E.; Sen'ko, D. A.; Nelyubina, Y. V.; Khoroshutina, Y. A.; Sukhorukov, A. Y.; Ioffe, S. L.
Org. Biomol. Chem.
2016, 14 (16), 3963–3974. doi: 10.1039/c6ob00388e
Tandem Pd-catalyzed C-C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes
Mikhaylov, A. A.; Dilman, A. D.; Novikov, R. A.; Khoroshutina, Y. A.; Struchkova, M. I.; Arkhipov, D. E.; Nelyubina, Y. V.; Tabolin, A. A.; Ioffe, S. L.
Tetrahedron Lett.
2016, 57 (1), 11–14. doi: 10.1016/j.tetlet.2015.10.091
Six-Membered Cyclic Nitroso Acetals: Synthesis and Studies of the Nitrogen Inversion Process of N-Silyloxy-3,6-dihydro-2H-1,2-oxazines
Shved, A. S.; Tabolin, A. A.; Novikov, R. A.; Nelyubina, Y. V.; Timofeev, V. P.; Ioffe, S. L.
European J. Org. Chem. 2016, 5569–5578. doi: 10.1002/ejoc.201600952
2015
Oximinoalkylamines as ligands for Cu-assisted azide-acetylene cycloaddition
Semakin, A. N.; Agababyan, D. P.; Kim, S.; Lee, S.; Sukhorukov, A. Y.; Fedina, K. G.; Oh, J.; Ioffe, S. L.
Tetrahedron Lett.
2015, 56 (46), 6335–6339. doi: 10.1016/j.tetlet.2015.09.106
Stereoselective Synthesis of Spirocyclic Nitronates by SnCl4-promoted Reaction of Nitroalkenes with C-2 Substituted 4-methylidene-1,3-dioxolane
Mikhaylov, A. A.; Zhmurov, P. A.; Naumova, A. S.; Khoroshutina, Y. A.; Sukhorukov, A. Y.; Ioffe, S. L.
Mendeleev Commun. 2015, 25 (6), 449–451. doi: 10.1016/j.mencom.2015.11.017
Synthesis of B,O,N-Doped Adamantanes and Diamantanes by Condensation of Oximes with Boronic Acids
Golovanov, I. S.; Sukhorukov, A. Y.; Nelyubina, Y. V.; Khomutova, Y. A.; Ioffe, S. L.; Tartakovsky, V. A.
J. Org. Chem.
2015, 80 (13), 6728–6736. doi: 10.1021/acs.joc.5b00892
Advances in the synthesis of 7-(3-cyclopentyloxy-4-methoxyphenyl)-hexahydro-3H-pyrrolizin-3-one (Pyrromilast)-a promising agent for treatment of chronic obstructive pulmonary disease
Boyko, Y. D.; Sukhorukov, A. Y.; Ioffe, S. L.; Tartakovsky, V. A.
Russ. Chem. Bull. 2015, 64 (6), 1240–1248. doi: 10.1007/s11172-015-1007-2
Formal [3+3]-cycloaddition of 3-methyl-5,6-dihydro-4H-1,2-oxazine-N-oxides with cyclopropane dicarboxylates under hyperbaric conditions
Tabolin, A. A.; Novikov, R. A.; Khomutova, Y. A.; Zharov, A. A.; Stashina, G. A.; Nelyubina, Y. V.; Tomilov, Y. V.; Ioffe, S. L.
Tetrahedron Lett.
2015, 56 (16), 2102–2105. doi: 10.1016/j.tetlet.2015.03.011
Synthesis of Tris(-oximinoalkyl)amines, New Tripodal N4 Ligands
Dorokhov, V. S.; Jung, H.; Kang, G.; Andreev, Y. A.; Semakin, A. N.; Oh, J.;
Sukhorukov, A. Y.; Ioffe, S. L.; Semenov, S. E.
Synth. Commun.
2015, 45 (11), 1362–1366. doi: 10.1080/00397911.2015.1021424
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