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Mendeleev Communications, 2009, Volume 19, Issue 5, Pages 276–278
DOI: https://doi.org/10.1016/j.mencom.2009.09.016
(Mi mendc3198)
 

This article is cited in 24 scientific papers (total in 24 papers)

Ionic-liquids-assisted reaction of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with β-nitrostyrenes

Yu. S. Syroeshkinaa, V. V. Kachalaa, I. V. Ovchinnikova, V. V. Kuznetsova, Yu. V. Nelyubinab, K. A. Lyssenkob, N. N. Makhovaa

a N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
b A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation
Abstract: 5,6-Diaryl-2,3-dihydro-1H-pyrazolo[1,2-a]pyrazolium tetrafluoroborates (hexafluorophosphate) were unexpectedly synthesized along with expected 1,3-diaryl-2-nitrotetrahydro-1H,5H-pyrazolo[1,2-a]pyrazoles, under the action of 1-nitro-2-(3-nitrophenyl)-ethylene on 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in ionic liquids with the Et2O·BF3 catalyst, whereas the same reaction with unsubstituted β-nitrostyrene produced only 1,3-diaryl-2-nitrotetrahydro-1H,5H-pyrazolo[1,2-a]pyrazole derivatives.
Document Type: Article
Language: English
Supplementary materials:
Supplementary_data_1.pdf (103.6 Kb)


Citation: Yu. S. Syroeshkina, V. V. Kachala, I. V. Ovchinnikov, V. V. Kuznetsov, Yu. V. Nelyubina, K. A. Lyssenko, N. N. Makhova, “Ionic-liquids-assisted reaction of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with β-nitrostyrenes”, Mendeleev Commun., 19:5 (2009), 276–278
Linking options:
  • https://www.mathnet.ru/eng/mendc3198
  • https://www.mathnet.ru/eng/mendc/v19/i5/p276
  • This publication is cited in the following 24 articles:
    1. V.V. Kuznetsov, D.V. Khakimov, A.I. Samigullina, A.S. Dmitrenok, “Synthesis and physical properties of new 1,6-diazabicyclo[4.1.0]heptanes: Quantum-chemistry calculations and crystal structures simulations”, Chemical Physics, 579 (2024), 112187  crossref
    2. Shubham Sharma, Pooja Sharma, Bharti Budhalakoti, Akshay Kumar, Kuldeep Singh, Rupender Kumar Kamboj, Kanchna Bhatrola, “Exploring the Impact of Ionic Liquids on Pyrazole Derivatives Synthesis: A Critical Review”, ChemistrySelect, 9:31 (2024)  crossref
    3. Emmanuel R. Buabeng, Md Shamim, Maged Henary, Comprehensive Heterocyclic Chemistry IV, 2022, 311  crossref
    4. V.V. Kuznetsov, D.V. Khakimov, A.S. Dmitrenok, A.S. Goloveshkin, “Synthesis, structure and peculiarity of conformational behavior of 1,5-diazabicyclo[3.1.0]hexanes”, Journal of Molecular Structure, 1269 (2022), 133856  crossref
    5. Alexander P Molchanov, Mariia M Efremova, Mariya A Kryukova, Mikhail A Kuznetsov, “Selective and reversible 1,3-dipolar cycloaddition of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones under microwave irradiation”, Beilstein J. Org. Chem., 16 (2020), 2679  crossref
    6. N. N. Makhova, L. I. Belen'kii, G. A. Gazieva, I. L. Dalinger, L. S. Konstantinova, V. V. Kuznetsov, A. N. Kravchenko, M. M. Krayushkin, O. A. Rakitin, A. M. Starosotnikov, L. L. Fershtat, S. A. Shevelev, V. Z. Shirinian, V. N. Yarovenko, “Progress in the chemistry of nitrogen-, oxygen- and sulfur-containing heterocyclic systems”, Russian Chem. Reviews, 89:1 (2020), 55–124  mathnet  mathnet  crossref  isi  scopus
    7. Ilya I. Marochkin, Vladimir V. Kuznetsov, Anatolii N. Rykov, Nina N. Makhova, Igor F. Shishkov, “Molecular structure study of 1,2,3-trimethyldiaziridine by means of gas electron diffraction method”, Struct Chem, 30:2 (2019), 457  crossref
    8. Ekaterina P. Altova, Vladimir V. Kuznetsov, Ilya I. Marochkin, Anatolii N. Rykov, Nina N. Makhova, Igor F. Shishkov, “3-Cyclopropyl-1,2-dimethyldiaziridine: synthesis and study of molecular structure by gas electron diffraction method”, Struct Chem, 29:3 (2018), 815  crossref
    9. Vladimir V. Kuznetsov, Ilya I. Marochkin, Alexander S. Goloveshkin, Nina N. Makhova, Igor F. Shishkov, “Comparable study of the structure of 1,2-bis(2-acetamidoethyl) diaziridine and 3,3-diethyldiaziridine with structures of related compounds by X-ray diffraction analysis and quantum chemical calculations”, Struct Chem, 28:4 (2017), 1211  crossref
    10. Mikhail I. Pleshchev, Nikita V. Das Gupta, Vladimir V. Kuznetsov, Ivan V. Fedyanin, Vadim V. Kachala, Nina N. Makhova, “CAN-mediated new, regioselective one-pot access to bicyclic cationic structures with 2,3-dihydro-1H-pyrazolo[1,2-a]pyrazol-4-ium core”, Tetrahedron, 71:47 (2015), 9012  crossref
    11. Lennart Lykke, Bjørn Dreiø Carlsen, Raoní Scheibler Rambo, Karl Anker Jørgensen, “Catalytic Asymmetric Synthesis of 4-Nitropyrazolidines: An Access to Optically Active 1,2,3-Triamines”, J. Am. Chem. Soc., 136:32 (2014), 11296  crossref
    12. N. N. Makhova, M. I. Pleshchev, M. A. Epishina, A. S. Kulikov, “Synthesis and Transformations of Nitrogen Heterocycles in Ionic Liquids (Review)”, Chem Heterocycl Comp, 50:5 (2014), 634  crossref
    13. V. V. Kuznetsov, V. V. Seregin, D. V. Khakimov, T. S. Pivina, M. D. Vedenyapina, A. A. Vedenyapin, N. N. Makhova, “The study of the formation mechanism of 1,2,3-trialkyldiaziridines by kinetic and quantum chemistry methods”, Russ Chem Bull, 63:9 (2014), 2000  crossref
    14. M. I. Pleshchev, V. Yu. Petukhova, V. V. Kuznetsov, D. V. Khakimov, T. S. Pivina, Yu. V. Nelyubina, N. N. Makhova, “Generation and metathesis of azomethine imines in reaction of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with het(aryl)methylidenemalononitriles”, Russ Chem Bull, 62:4 (2013), 1066  crossref
    15. M. I. Pleshchev, V. V. Kachala, A. S. Goloveshkin, I. S. Bushmarinov, V. V. Kuznetsov, D. V. Khakimov, N. N. Makhova, “Unexpected regioselectivities of [3 + 2] cycloaddition of azomethine imines to acrylonitrile and 4-nitrophenyl vinyl sulfone”, Mendeleev Commun., 23:5 (2013), 271–273  mathnet  crossref
    16. M. I. Pleshchev, V. Yu. Petukhova, V. V. Kuznetsov, D. V. Khakimov, T. S. Pivina, M. I. Struchkova, Yu. V. Nelyubina, N. N. Makhova, “Metathesis of Azomethine Imines in Reaction of 6-aryl-1,5-Diazabicyclo[3.1.0]Hexanes with (Het)Arylidenemalononitriles”, Mendeleev Commun., 23:1 (2013), 34–36  mathnet  crossref
    17. M. I. Pleshchev, M. A. Epishina, V. V. Kachala, V. V. Kuznetsov, A. S. Goloveshkin, I. S. Bushmarinov, N. N. Makhova, “Ionic liquid-promoted stereoselective [3 + 2] cycloaddition of 1-hetaryl-2-nitroethenes to azomethine imines generated in situ”, Mendeleev Commun., 23:4 (2013), 206–208  mathnet  crossref
    18. V. V. Kuznetsov, V. V. Seregin, A. A. Laptev, D. V. Khakimov, T. S. Pivina, A. P. Simakova, M. D. Vedenyapina, A. A. Vedenyapin, N. N. Makhova, “Kinetic and quantum chemical studies of the mechanism of formation of 1,2-dialkyldiaziridines”, Russ Chem Bull, 61:6 (2012), 1121  crossref
    19. V. Yu. Petukhova, M. I. Pleshchev, L. L. Fershtat, V. V. Kuznetsov, V. V. Kachala, N. N. Makhova, “Metathesis of azomethine imines in the reaction of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with carbonyl compounds”, Mendeleev Commun., 22:1 (2012), 32–34  mathnet  crossref
    20. David A. Capretto, Chad Brouwer, Catherine B. Poor, Chuan He, “Gold(I)-Catalyzed Formation of 3-Pyrazolines through Cycloaddition of Diaziridine to Alkynes”, Org. Lett., 13:21 (2011), 5842  crossref
    Citing articles in Google Scholar: Russian citations, English citations
    Related articles in Google Scholar: Russian articles, English articles
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