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4-(N-Boc-amino)-1Н-1,2,3-triazolecarbothioamides in the synthesis of a new heterocyclic [1,2,3]triazolo[4,5-e][1,4]thiazepine system

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Chemistry of Heterocyclic Compounds Aims and scope

4-(N-Boc-amino)-1Н-1,2,3-triazolecarbothioamides, obtained by a sequential treatment of 4-(N-Boc-amino)-1Н-1,2,3-triazoles with n-BuLi and alkyl isothiocyanates at –78÷–60°C, reacted with ethyl bromoacetate, forming the respective 4-(N-Boc-amino)-5-thioimidates, which underwent intramolecular cyclocondensation upon treatment in saturated НCl solution in dioxane, producing 8-(alkylimino)-4,8-dihydro-1Н-[1,2,3]triazolo[4,5-e][1,4]thiazepin-5(6Н)-ones.

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Authors and Affiliations

  1. National University “Kyiv-Mohyla Academy”, 2 Hryhorija Skovorody St., Kyiv, 04655, Ukraine

    Natalia A. Syrota

  2. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv, 02660, Ukraine

    Sergiy V. Kemskiy, Andriy V. Bol’but, Igor I. Chernobaev, Oleksandr S. Liavinets & Mykhailo V. Vovk

  3. Enamine Ltd., 78 Chervonotkatska St., Kyiv, 02094, Ukraine

    Andriy V. Bol’but

Authors
  1. Natalia A. Syrota
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  2. Sergiy V. Kemskiy
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  3. Andriy V. Bol’but
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  4. Igor I. Chernobaev
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  5. Oleksandr S. Liavinets
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  6. Mykhailo V. Vovk
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Correspondence to Sergiy V. Kemskiy.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(7/8), 841–847

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Syrota, N.A., Kemskiy, S.V., Bol’but, A.V. et al. 4-(N-Boc-amino)-1Н-1,2,3-triazolecarbothioamides in the synthesis of a new heterocyclic [1,2,3]triazolo[4,5-e][1,4]thiazepine system. Chem Heterocycl Comp 57, 841–847 (2021). https://doi.org/10.1007/s10593-021-02989-1

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  • DOI: https://doi.org/10.1007/s10593-021-02989-1

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