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Mendeleev Communications, 2017, Volume 27, Issue 2, Pages 128–130
DOI: https://doi.org/10.1016/j.mencom.2017.03.006
(Mi mendc1918)
 

This article is cited in 13 scientific papers (total in 13 papers)

Communications

Syntheses of chiral nopinane-annelated pyridines of C2 and D2-symmetry: X-ray structures of the fused derivatives of 4,5-diazafluorene, 4,5-diaza-9H-fluoren-9-one, and 9,9’-bi-4,5-diazafluorenylidene

E. S. Vasilyeva, I. Yu. Bagryanskayaa, A. V. Tkachevab

a N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russian Federation
b Department of Natural Sciences, Novosibirsk State University, Novosibirsk, Russian Federation
Abstract: Reaction of (+)-pinocarvone oxime with 2-morpholinocyclopent-2-enone and FeCl3·6H2O affords chiral C2-symmetric fused derivative of 4,5-diazafluorene, whose oxidation with SeO2 gives nopinane-annelated derivatives of 4,5-diaza-9Hfluoren- 9-one (C2-symmetry) and of 9,9-bi-4,5-diazafluorenylidene (D2-symmetry). Structures of the compounds synthesized were proved by X-ray crystallography.
Document Type: Article
Language: English
Supplementary materials:
Supplementary_data_1.pdf (990.9 Kb)


Citation: E. S. Vasilyev, I. Yu. Bagryanskaya, A. V. Tkachev, “Syntheses of chiral nopinane-annelated pyridines of C2 and D2-symmetry: X-ray structures of the fused derivatives of 4,5-diazafluorene, 4,5-diaza-9H-fluoren-9-one, and 9,9’-bi-4,5-diazafluorenylidene”, Mendeleev Commun., 27:2 (2017), 128–130
Linking options:
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  • https://www.mathnet.ru/eng/mendc/v27/i2/p128
  • This publication is cited in the following 13 articles:
    1. D. V. Zubricheva, E. S. Vasilyev, S. N. Bizyaev, V. D. Tikhova, A. V. Tkachev, “DIPINODIAZAFLUORENES AS REAGENTS FOR SELECTIVE EXTRACTION OF PALLADIUM, GOLD AND RUTHENIUM”, Doklady Rossijskoj akademii nauk. Himiâ, nauki o materialah., 510:1 (2023), 35  crossref
    2. D. V. Zubricheva, E. S. Vasilyev, S. N. Bizyaev, V. D. Tikhova, A. V. Tkachev, “Dipinodiazafluorenes as Reagents for the Selective Extraction of Palladium, Gold, and Ruthenium”, Dokl Chem, 510:2 (2023), 137  crossref
    3. Tatyana E. Kokina, Nikita A. Shekhovtsov, Eugene S. Vasilyev, Ludmila A. Glinskaya, Aleksandr V. Mikheylis, Victor F. Plyusnin, Alexey V. Tkachev, Mark B. Bushuev, “Efficient emission of Zn(ii) and Cd(ii) complexes with nopinane-annelated 4,5-diazafluorene and 4,5-diazafluoren-9-one ligands: how slight structural modification alters fluorescence mechanism”, Dalton Trans., 52:22 (2023), 7429  crossref
    4. Yuliya P. Ustimenko, Alexander M. Agafontsev, Aleksey V. Tkachev, “Synthesis of chiral pinopyridines using catalysis by metal complexes”, Chem Heterocycl Comp, 58:2-3 (2022), 135  crossref
    5. Iakov S. Fomenko, Medhanie Afewerki, Marko I. Gongola, Eugene S. Vasilyev, Lidia S. Shul'pina, Nikolay S. Ikonnikov, Georgiy B. Shul'pin, Denis G. Samsonenko, Vadim V. Yanshole, Vladimir A. Nadolinny, Alexander N. Lavrov, Alexey V. Tkachev, Artem L. Gushchin, “Novel Copper(II) Complexes with Dipinodiazafluorene Ligands: Synthesis, Structure, Magnetic and Catalytic Properties”, Molecules, 27:13 (2022), 4072  crossref
    6. Vladimir V. Chernyshov, Irina I. Popadyuk, Olga I. Yarovaya, Nariman F. Salakhutdinov, “Nitrogen-Containing Heterocyclic Compounds Obtained from Monoterpenes or Their Derivatives: Synthesis and Properties”, Top Curr Chem (Z), 380:5 (2022)  crossref
    7. Eugene S. Vasilyev, Sergey N. Bizyaev, Vladislav Yu Komarov, Alexey V. Tkachev, “Bistricyclic aromatic enes annelated with nopinane fragment”, Tetrahedron, 83 (2021), 131979  crossref
    8. Eugene S. Vasilyev, Sergey N. Bizyaev, Vladislav Yu. Komarov, Yury V. Gatilov, Alexey V. Tkachev, “Chiral C2-Symmetric Diimines with 4,5-Diazafluorene Units”, Molecules, 24:17 (2019), 3186  crossref
    9. E. S. Vasilyev, S. N. Bizyaev, V. Yu. Komarov, A. V. Tkachev, “Syntheses of chiral fused 4,5-diazafluorene–bis(nopinane) derivatives”, Mendeleev Commun., 29:5 (2019), 584–586  mathnet  crossref
    10. Olimpia Mamula, Thomas Bark, Boris Quinodoz, Helen Stoeckli-Evans, Alex von Zelewsky, “Self-assembly of Ag(I) helicates with new enantiopure 5,6-Chiragen type ligands”, Inorganica Chimica Acta, 475 (2018), 200  crossref
    11. Yu. P. Ustimenko, A. M. Agafontsev, V. Yu. Komarov, A. V. Tkachev, “Synthesis of chiral nopinane annelated 3-methyl-1-aryl-1H-pyrazolo[3,4-b]pyridines by condensation of pinocarvone oxime with 1-aryl-1H-pyrazol-5-amines”, Mendeleev Commun., 28:6 (2018), 584–586  mathnet  crossref
    12. T. E. Kokina, L. A. Glinskaya, E. S. Vasiliev, M. I. Rakhmanova, S. V. Makarova, D. A. Piryazev, I. V. Korol'kov, A. V. Tkachev, S. V. Larionov, “Structure and photoluminescence of Zn(II) and Sd(II) complexes with chiral bis-pyridine containing fragments of natural (–)-α-pinene”, J Struct Chem, 58:5 (2017), 994  crossref
    13. Yakov S. Fomenko, Artem L. Gushchin, Aleksey V. Tkachev, Evgene S. Vasilyev, Pavel A. Abramov, Vladimir A. Nadolinny, Mikhail M. Syrokvashin, Maxim N. Sokolov, “Fist oxidovanadium complexes containing chiral derivatives of dihydrophenanthroline and diazafluorene”, Polyhedron, 135 (2017), 96  crossref
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