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Synthesis of pyrazolo- and [1,2,4]triazolo-[1,5-а]quinolin-9-ols by cycloaddition to 8-hydroxyquinoline N-imide

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Chemistry of Heterocyclic Compounds Aims and scope

The reaction of 1-amino-8-hydroxyquinolinium mesitylenesulfonate with alkenes and alkynes containing electron-withdrawing substituents was performed in MeCN–K2СО3 system and gave the respective 9-hydroxypyrazolo[1,5-a]quinolines. The reaction with acetonitrile\ and aromatic nitriles in aqueous 2 N KОН solution gave the respective 2-substituted 9-hydroxy[1,2,4]triazolo[1,5-a]quinolines.

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This work was performed with financial support from the Russian Science Foundation (grant 18-73-00133).

The analytical and spectral studies were performed at the Chemical Service Center of the Siberian Branch, Russian Academy of Sciences.

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Authors and Affiliations

  1. Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences, 5 Akademika Lavrentieva Ave, Novosibirsk, 630090, Russia

    Vasilii E. Evtushok

  2. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave, Novosibirsk, 630090, Russia

    Aleksey Yu. Vorob’ev

  3. Novosibirsk State University, 1 Pirogova St, Novosibirsk, 630090, Russia

    Aleksey Yu. Vorob’ev

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  1. Vasilii E. Evtushok
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  2. Aleksey Yu. Vorob’ev
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Correspondence to Aleksey Yu. Vorob’ev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(3), 229–234

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Evtushok, V.E., Vorob’ev, A.Y. Synthesis of pyrazolo- and [1,2,4]triazolo-[1,5-а]quinolin-9-ols by cycloaddition to 8-hydroxyquinoline N-imide. Chem Heterocycl Comp 55, 229–234 (2019). https://doi.org/10.1007/s10593-019-02446-0

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  • DOI: https://doi.org/10.1007/s10593-019-02446-0

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