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Mendeleev Communications, 2014, Volume 24, Issue 4, Pages 203–205
DOI: https://doi.org/10.1016/j.mencom.2014.06.004
(Mi mendc2523)
 

This article is cited in 19 scientific papers (total in 19 papers)

Communications

5-Nitro-7,8-furoxanoquinoline: a new type of fused nitroarenes possessing Diels–Alder reactivity

M. A. Bastrakova, A. M. Starosotnikova, I. V. Fedyaninb, V. V. Kachalaa, S. A. Sheveleva

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: Reaction of 8-chloro-5,7-dinitroquinoline with sodium azide afforded isomeric 5-nitro-7,8-furoxanoquinolines, whose nitroethene fragment can act as dienophile and heterodiene in the Diels–Alder cycloaddition.
Document Type: Article
Language: English


Citation: M. A. Bastrakov, A. M. Starosotnikov, I. V. Fedyanin, V. V. Kachala, S. A. Shevelev, “5-Nitro-7,8-furoxanoquinoline: a new type of fused nitroarenes possessing Diels–Alder reactivity”, Mendeleev Commun., 24:4 (2014), 203–205
Linking options:
  • https://www.mathnet.ru/eng/mendc2523
  • https://www.mathnet.ru/eng/mendc/v24/i4/p203
  • This publication is cited in the following 19 articles:
    1. Il'ya I. Ustinov, Yurii M. Atroshchenko, “Nitroquinolines in the Synthesis of Heterocyclic Compounds (microreview)”, Chem Heterocycl Comp, 59:1-2 (2023), 35  crossref
    2. Alexey M. Starosotnikov, Maxim A. Bastrakov, “Recent Developments in the Synthesis of HIV-1 Integrase Strand Transfer Inhibitors Incorporating Pyridine Moiety”, IJMS, 24:11 (2023), 9314  crossref
    3. A. M. Starosotnikov, M. A. Bastrakov, “Synthesis of new polynuclear heterocyclic systems based on 7,8-diamino-5-nitroquinoline”, Russ Chem Bull, 72:11 (2023), 2754  crossref
    4. Alexey M. Starosotnikov, Maxim A. Bastrakov, Heterocycles, 2022, 27  crossref
    5. Nina N. Makhova, Leonid L. Fershtat, Comprehensive Heterocyclic Chemistry IV, 2022, 190  crossref
    6. M. A. Bastrakov, A. K. Fedorenko, A. M. Starosotnikov, “Synthesis of 6-R-isoxazolo[4,3-b]pyridines and their reactions with C-nucleophiles”, Russ Chem Bull, 69:2 (2020), 394  crossref
    7. Maxim A. Bastrakov, Alexey K. Fedorenko, Alexey M. Starosotnikov, Ivan V. Fedyanin, Vladimir A. Kokorekin, “Synthesis and Facile Dearomatization of Highly Electrophilic Nitroisoxazolo[4,3-b]pyridines”, Molecules, 25:9 (2020), 2194  crossref
    8. S. G. Zlotin, I. L. Dalinger, N. N. Makhova, V. A. Tartakovsky, “Nitro compounds as the core structures of promising energetic materials and versatile reagents for organic synthesis”, Russian Chem. Reviews, 89:1 (2020), 1–54  mathnet  mathnet  crossref  isi  scopus
    9. 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
    10. Nikita S. Fedik, Mikhail E. Kletskii, Oleg N. Burov, Anton V. Lisovin, Sergey V. Kurbatov, Vladimir A. Chistyakov, Pavel G. Morozov, “Comprehensive study of nitrofuroxanoquinolines. New perspective donors of NO molecules”, Nitric Oxide, 93 (2019), 15  crossref
    11. Alexey M. Starosotnikov, Maxim A. Bastrakov, Vadim V. Kachala, Ivan V. Fedyanin, Svyatoslav A. Shevelev, Igor L. Dalinger, “Unusual Pericyclic Reactivity of 4‐Nitrobenzofuroxans in 1,3‐Dipolar Cycloaddition with N‐Benzyl Azomethine Ylide – A New Example of Multiple C–C‐Bond Forming Transformations.”, ChemistrySelect, 3:34 (2018), 9773  crossref
    12. Mikhail E. Kletskii, Oleg N. Burov, Nikita S. Fedik, Sergey V. Kurbatov, “Thiol-induced nitric oxide donation mechanisms in substituted dinitrobenzofuroxans”, Nitric Oxide, 62 (2017), 44  crossref
    13. N. A. Troitskaya-Markova, O. G. Vlasova, T. I. Godovikova, S. G. Zlotin, O. A. Rakitin, “Bis[1,2,5]oxadiazolo[3,4-c:3',4'-e]pyridazine 4,5-dioxide as a synthetic equivalent of 4,4'-dinitroso-3,3'-bifurazan”, Mendeleev Commun., 27:5 (2017), 448–450  mathnet  crossref
    14. Maxim A. Bastrakov, Alexey M. Starosotnikov, Alexander A. Pavlov, Igor L. Dalinger, Svyatoslav A. Shevelev, “Synthesis of novel polycyclic heterosystems from 5-nitro[1,2,5]selenadiazolo[3,4-e]benzofuroxans”, Chem Heterocycl Comp, 52:9 (2016), 690  crossref
    15. Yulia P. Semenyuk, Pavel G. Morozov, Oleg N. Burov, Mikhail E. Kletskii, Anton V. Lisovin, Sergey V. Kurbatov, François Terrier, “Sequential SNAr and Diels–Alder reactivity of superelectrophilic 10π heteroaromatic substrates”, Tetrahedron, 72:18 (2016), 2254  crossref
    16. V. A. Ogurtsov, A. V. Shastin, S. G. Zlotin, O. A. Rakitin, “Unusual transformation of 3-alkylfuroxans into 3-(nitrooxyalkyl)furoxans on treatment with a mixture of nitric and sulfuric acids”, Russ Chem Bull, 65:12 (2016), 2901  crossref
    17. A. M. Starosotnikov, M. A. Bastrakov, A. A. Pavlov, I. V. Fedyanin, I. L. Dalinger, S. A. Shevelev, “Synthesis of novel polycyclic heterosystems based on 5-nitro[1,2,5]thiadiazolo[3,4-e]benzofuroxan”, Mendeleev Commun., 26:3 (2016), 217–219  mathnet  crossref
    18. Dmitry V. Steglenko, Svyatoslav A. Shevelev, Mikhail E. Kletskii, Oleg N. Burov, Anton V. Lisovin, Alexey M. Starosotnikov, Pavel G. Morozov, Sergey V. Kurbatov, Vladimir I. Minkin, Maxim A. Bastrakov, “Quantum-chemical and NMR study of nitrofuroxanoquinoline cycloaddition”, Chem Heterocycl Comp, 51:9 (2015), 845  crossref
    19. L. S. Konstantinova, S. A. Amelichev, S. G. Zlotin, M. I. Struchkova, T. I. Godovikova, O. A. Rakitin, “[1,4]Dithiino[2,3-c:5,6-c' ]bis[1,2,5]oxadiazole di-N-oxide: synthesis and oxidation to mono- and bis-S-oxides”, Mendeleev Commun., 25:5 (2015), 339–340  mathnet  crossref
    Citing articles in Google Scholar: Russian citations, English citations
    Related articles in Google Scholar: Russian articles, English articles
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