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Intramolecular cyclization of 2-(heteroarylsulfanyl)-N-(3-oxoalkenyl)acetamides: synthesis of 3-(heteroarylsulfanyl)- and 3-sulfanylpyridin-2(1H)-ones

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Chemistry of Heterocyclic Compounds Aims and scope

The reaction of 2-chloro-N-(3-oxoalkenyl)acetamides with 1,3-benzothiazole-2(3H)-thione, 1,3-benzoxazole-2(3H)-thione, and 1-methyl-1,3-dihydro-2H-benzimidazole-2-thione led to the formation of 2-(heteroarylsulfanyl)-N-(3-oxoalkenyl)acetamides. By the action of a base, these compounds were converted into pyridin-2(1H)-ones containing a divalent sulfur atom in position C-3 bonded to a heterocyclic ring. Bromination, nitration, alkylation of 3-(1,3-benzothiazol-2-ylsulfanyl)pyridin-2(1H)-ones have been studied. The action of zinc in acetic acid transformed these compounds into 3-sulfanylpyridin-2(1H)-ones.

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This work was supported by the Russian Science Foundation (grant 19-13-00273).

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Authors and Affiliations

  1. Dostoevsky Omsk State University, 55a Mira Ave., Omsk, 644077, Russia

    Olga А. Savchenko, Dmitry S. Goncharov & Yulia P. Bogza

  2. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 S. Kovalevskoi 22 / 20 Akademicheskaya St., Yekaterinburg, 620108, Russia

    Vera V. Musiyak

  3. Omsk State Technical University, 11. Mira Ave., Omsk, 644050, Russia

    Anton L. Shatsauskas, Evgeny B. Ulyankin & Alexander S. Fisyuk

  4. Center of New Chemical Technologies, Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences, 54 Neftezavodskaya St., Omsk, 644040, Russia

    Valentin P. Talzi & Sergey N. Evdokimov

Authors
  1. Olga А. Savchenko
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  2. Vera V. Musiyak
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  3. Dmitry S. Goncharov
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  9. Alexander S. Fisyuk
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Correspondence to Alexander S. Fisyuk.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(9), 1180–1186

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Savchenko, O.А., Musiyak, V.V., Goncharov, D.S. et al. Intramolecular cyclization of 2-(heteroarylsulfanyl)-N-(3-oxoalkenyl)acetamides: synthesis of 3-(heteroarylsulfanyl)- and 3-sulfanylpyridin-2(1H)-ones. Chem Heterocycl Comp 56, 1180–1186 (2020). https://doi.org/10.1007/s10593-020-02795-1

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  • DOI: https://doi.org/10.1007/s10593-020-02795-1

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