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Acylating and arylsulfonylating ability of O-derivatives of isatin 3-oximes

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

O-Acyl and O-arylsulfonyl derivatives of isatin 3-oximes have been synthesized and their interaction with alcohols and amines has been investigated. It was established that none of the esters of 1-substituted isatin 3-oximes reacted with the indicated nucleophiles. 1-Unsubstituted O-aryl and O-arylsulfonyl derivatives react with amines as acylating agents even at room temperature, but O-acetyl derivatives only on heating. Acylamides or arylsulfamides respectively are formed in this way. O-Acyl derivatives do not react with alcohols at room temperature. Only O-benzoyl derivatives form ethyl benzoate on heating in ethanol. A comparative analysis of mass spectrometric data on the processes of acylation and arylsulfonylation is given.

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Authors and Affiliations

  1. Institute of Cardiology, Kaunas Medical University, Kaunas, 50009, Lithuania

    A. P. Stankevicius & L. N. Janushene

  2. M. V. Lomonosov Moscow State University, Moscow, 119899, Russia

    P. B. Terentiev

  3. Kaunas Medical University, Kaunas, 44307, Lithuania

    A. B. Savickas

Authors
  1. A. P. Stankevicius
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  2. P. B. Terentiev
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  3. L. N. Janushene
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  4. A. B. Savickas
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 113–119, January, 2005.

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Stankevicius, A.P., Terentiev, P.B., Janushene, L.N. et al. Acylating and arylsulfonylating ability of O-derivatives of isatin 3-oximes. Chem Heterocycl Compd 41, 98–104 (2005). https://doi.org/10.1007/s10593-005-0114-7

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  • DOI: https://doi.org/10.1007/s10593-005-0114-7

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