Abstract:
Ring opening in 6-aryl-1,5-diazabicyclo[3.1.0]hexanes gives cyclic azomethine imines which are prone to exchange of arylidene moiety with (het)arylidenemalononitriles to form the metathesis products being new azomethine imines. These species were fixed as pyrazolines due to the 1,4-H shift or trapped by dimethyl acetylenedicarboxylate or CS2.
Citation:
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
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This publication is cited in the following 28 articles:
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
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
Alexander A. Penney, Mariia M. Efremova, Alexander P. Molchanov, Mariya A. Kryukova, Andrey Yu. Kudinov, Alexander S. Bunev, Valentina M. Keresten, Mikhail A. Kuznetsov, “1,3‐Dipolar versus Nucleophilic Reactivity of Diaziridines Based on 3,4‐Dihydroisoquinoline toward Aryl Iso(thio)cyanates”, ChemistrySelect, 7:30 (2022)
A. P. Molchanov, M. M. Efremova, M. A. Kuznetsov, “Cyclopropenes and methylenecyclopropanes in 1,3-dipolar cycloaddition reactions”, Russ Chem Bull, 71:4 (2022), 620
Dmitry V. Khakimov, Leonid L. Fershtat, Tatyana S. Pivina, Nina N. Makhova, “Nitrodiaziridines: Unattainable yet, but Desired Energetic Materials”, J. Phys. Chem. A, 125:18 (2021), 3920
Zetryana Puteri Tachrim, Lei Wang, Yuta Murai, Makoto Hashimoto, “New Trends in Diaziridine Formation and Transformation (a Review)”, Molecules, 26:15 (2021), 4496
Sundaresan Ravindra, C. P. Irfana Jesin, Arivalagan Shabashini, Ganesh Chandra Nandi, “Recent Advances in the Preparations and Synthetic Applications of Oxaziridines and Diaziridines”, Adv Synth Catal, 363:7 (2021), 1756
Leonid S. Khaikin, Georgiy G. Ageev, Anatoliy N. Rykov, Olga E. Grikina, Igor F. Shishkov, Igor V. Kochikov, Vladimir V. Kuznetsov, Nina N. Makhova, Sergei S. Bukalov, Larisa A. Leites, “Equilibrium molecular structure and spectra of 6-methyl-1,5-diazabicyclo[3.1.0]hexane: joint analysis of gas phase electron diffraction, quantum chemistry, and spectroscopic data”, Phys. Chem. Chem. Phys., 22:39 (2020), 22477
L. S. Khaikin, G. G. Ageev, O. E. Grikina, I. F. Shishkov, V. V. Kuznetsov, N. N. Makhova, “Intramolecular Motions in 1,2,3-Triethyldiaziridine: A Quantum Chemistry Study”, Russ. J. Phys. Chem., 94:9 (2020), 1836
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
Uroš Grošelj, Jurij Svete, Jeffery Aubé, Organic Reactions, 2020, 529
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
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
V. V. Kuznetsov, V. V. Kachala, N. N. Makhova, “Synthesis of hybrid structures comprising diaziridine and cyclopropane rings in one molecule”, Mendeleev Commun., 28:5 (2018), 497–500
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
Yu. B. Koptelov, A. P. Molchanov, R. R. Kostikov, “Regio- and diastereoselective cycloaddition of stable cyclic azomethine imines to N-arylitaconimides”, Russ J Org Chem, 51:8 (2015), 1134
Galina A. Gazieva, Alexei N. Izmest'ev, Yulia V. Nelyubina, Natalya G. Kolotyrkina, Igor E. Zanin, Angelina N. Kravchenko, “Synthesis of imidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazine-2,8-diones via a rearrangement of imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-2,7-diones in the reaction with isatins”, RSC Adv., 5:55 (2015), 43990
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
M. A. Epishina, A. S. Kulikov, N. V. Ignat'ev, M. Schulte, N. N. Makhova, “Efficient synthesis of tertiary acyclic amides by the Chapman rearrangement of aryl benzimidates in ionic liquids”, Mendeleev Commun., 25:2 (2015), 126–128
M. I. Pleshchev, N. V. Das Gupta, M. I. Struchkova, A. S. Goloveshkin, I. S. Bushmarinov, D. V. Khakimov, N. N. Makhova, “Regio- and stereoselective cycloaddition of stable azomethine imines to (arylmethylidene)malononitriles”, Mendeleev Commun., 25:3 (2015), 188–190
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