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Mendeleev Communications, 2015, Volume 25, Issue 4, Pages 257–259
DOI: https://doi.org/10.1016/j.mencom.2015.07.007
(Mi mendc2371)
 

This article is cited in 28 scientific papers (total in 28 papers)

Communications

Ionic liquid-mediated synthesis of (1H-1,2,3-triazol-1-yl)furoxans by [3 + 2] cycloaddition of azidofuroxans to acetylenes

L. L. Fershtat, S. S. Ashirbaev, A. S. Kulikov, V. V. Kachala, N. N. Makhova

N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
Abstract: The [3 + 2] cycloaddition of azidofuroxans to internal and terminal acetylenes was found to occur only in ionic liquids on heating and afford (1H-1,2,3-triazol-1-yl)furoxans in moderate to good yields. The reaction with terminal acetylenes proceeds with high regio- selectivity.
Document Type: Article
Language: English
Supplementary materials:
Supplementary_data_1.pdf (192.6 Kb)


Citation: L. L. Fershtat, S. S. Ashirbaev, A. S. Kulikov, V. V. Kachala, N. N. Makhova, “Ionic liquid-mediated synthesis of (1H-1,2,3-triazol-1-yl)furoxans by [3 + 2] cycloaddition of azidofuroxans to acetylenes”, Mendeleev Commun., 25:4 (2015), 257–259
Linking options:
  • https://www.mathnet.ru/eng/mendc2371
  • https://www.mathnet.ru/eng/mendc/v25/i4/p257
  • This publication is cited in the following 28 articles:
    1. Nilakshi Dutta, Priyanuj K. Hazarika, Samprity Sarmah, Diganta Sarma, Reference Module in Chemistry, Molecular Sciences and Chemical Engineering, 2024  crossref
    2. V. N. Charushin, E. V. Verbitskiy, O. N. Chupakhin, D. V. Vorobyeva, P. S. Gribanov, S. N. Osipov, A. V. Ivanov, S. V. Martynovskaya, E. F. Sagitova, V. D. Dyachenko, I. V. Dyachenko, S. G. Krivokolylsko, V. V. Dotsenko, A. V. Aksenov, D. A. Aksenov, N. A. Aksenov, A. A. Larin, L. L. Fershtat, V. M. Muzalevskiy, V. G. Nenajdenko, A. V. Gulevskaya, A. F. Pozharskii, E. A. Filatova, K. V. Belyaeva, B. A. Trofimov, I. A. Balova, N. A. Danilkina, A. I. Govdi, A. S. Tikhomirov, A. E. Shchekotikhin, M. S. Novikov, N. V. Rostovskii, A. F. Khlebnikov, Yu. N. Klimochkin, M. V. Leonova, I. M. Tkachenko, V. A.-o. Mamedov, V. L. Mamedova, N. A. Zhukova, V. E. Semenov, O. G. Sinyashin, O. V. Borshchev, Yu. N. Luponosov, S. A. Ponomarenko, A. S. Fisyuk, A. S. Kostyuchenko, V. G. Ilkin, T. V. Beryozkina, V. A. Bakulev, A. S. Gazizov, A. A. Zagidullin, A. A. Karasik, M. E. Kukushkin, E. K. Beloglazkina, N. E. Golantsov, A. A. Festa, L. G. Voskresenskii, V. S. Moshkin, E. M. Buev, V. Ya. Sosnovskikh, I, “The chemistry of heterocycles in the 21st century”, Russian Chem. Reviews, 93:7 (2024), RCR5125  mathnet  mathnet  crossref  isi  scopus
    3. Irina A. Stebletsova, Alexander A. Larin, Ivan V. Ananyev, Leonid L. Fershtat, “Regioselective Synthesis of NO-Donor (4-Nitro-1,2,3-triazolyl)furoxans via Eliminative Azide–Olefin Cycloaddition”, Molecules, 28:19 (2023), 6969  crossref
    4. Joseph Yount, Davin G. Piercey, “Electrochemical Synthesis of High-Nitrogen Materials and Energetic Materials”, Chem. Rev., 122:9 (2022), 8809  crossref
    5. Nina N. Makhova, Leonid L. Fershtat, Comprehensive Heterocyclic Chemistry IV, 2022, 190  crossref
    6. Dmitry M. Bystrov, Leonid L. Fershtat, Nina N. Makhova, “Synthesis and reactivity of aminofuroxans”, Chem Heterocycl Comp, 55:12 (2019), 1143  crossref
    7. L. S. Konstantinova, E. A. Knyazeva, Yu. V. Gatilov, S. G. Zlotin, O. A. Rakitin, “Nitro derivatives of 2,1,3-benzothiadiazole 1-oxides: synthesis, structural study, and NO release”, Russ Chem Bull, 67:1 (2018), 95  crossref
    8. Nina N. Makhova, Leonid L. Fershtat, “Recent advances in the synthesis and functionalization of 1,2,5-oxadiazole 2-oxides”, Tetrahedron Letters, 59:24 (2018), 2317  crossref
    9. N. V. Obruchnikova, R. A. Novikov, S. G. Zlotin, P. V. Dorovatovskii, V. N. Khrustalev, O. A. Rakitin, “Synthesis and structural investigation of 4,4′-dimethyl-[3,3′-bi(1,2,5-oxadiazole)] 5,5′-dioxide”, Russ Chem Bull, 67:11 (2018), 2044  crossref
    10. E. Yu. Schmidt, I. A. Bidusenko, N. A. Cherimichkina, B. A. Trofimov, “Acetylene as driving and organizing molecule in the assembling reactions with chalcones in the NaOBut/DMSO superbase system”, Mendeleev Commun., 28:1 (2018), 47–48  mathnet  crossref
    11. Alexander A. Larin, Leonid L. Fershtat, Ivan V. Ananyev, Nina N. Makhova, “Versatile approach to heteroarylfuroxan derivatives from oximinofuroxans via a one-pot, nitration/thermolysis/[3+2]-cycloaddition cascade”, Tetrahedron Letters, 58:42 (2017), 3993  crossref
    12. Leonid L. Fershtat, Nina N. Makhova, “Molecular Hybridization Tools in the Development of Furoxan‐Based NO‐Donor Prodrugs”, ChemMedChem, 12:9 (2017), 622  crossref
    13. Petr A. Zhmurov, Yulia A. Khoroshutina, Roman A. Novikov, Ivan S. Golovanov, Alexey Yu. Sukhorukov, Sema L. Ioffe, “Divergent Reactivity of In Situ Generated Metal Azides: Reaction with N,N‐Bis(oxy)enamines as a Case Study”, Chemistry A European J, 23:19 (2017), 4570  crossref
    14. Alexander S. Kulikov, Margarita A. Epishina, Leonid L. Fershtat, Anna A. Romanova, Nina N. Makhova, “Effective synthesis of 6-substituted 7H-tetrazolo[5,1-b][1,3,4]thiadiazines via a one-pot condensation/nitrosation/azide-tetrazole tautomerism reaction sequence”, Tetrahedron Letters, 58:42 (2017), 3998  crossref
    15. L. Annaratone, S. Guglielmo, K. Yu. Chegaev, “Direct introduction of cyano group on furoxan ring”, Mendeleev Commun., 27:6 (2017), 565–566  mathnet  crossref
    16. 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
    17. A. V. Okhlobystina, A. O. Okhlobystin, N. N. Letichevskaya, V. F. Abdulaeva, N. O. Movchan, N. T. Berberova, “An alternative method for the desulfurization of hydrocarbon fuels”, Mendeleev Commun., 27:1 (2017), 104–105  mathnet  crossref
    18. M. G. Chernysheva, A. E. Averina, O. A. Soboleva, G. A. Badun, “Radionuclide and tensiometry approaches to studying lysozyme behaviors in water–ionic liquid systems”, Mendeleev Commun., 27:3 (2017), 296–298  mathnet  crossref
    19. Leonid L. Fershtat, Alexander A. Larin, Margarita A. Epishina, Alexander S. Kulikov, Igor V. Ovchinnikov, Ivan V. Ananyev, Nina N. Makhova, “Regioselective synthesis of bifuroxanyl systems with the 3-nitrobifuroxanyl core via a one-pot acylation/nitrosation/cyclization cascade”, Tetrahedron Letters, 57:38 (2016), 4268  crossref
    20. 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
    Citing articles in Google Scholar: Russian citations, English citations
    Related articles in Google Scholar: Russian articles, English articles
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