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Synthesis of 4-trifluoromethyl-3,4-dihydro-1,3,5-triazino[2,1-a]isoindol-2-ones by cyclocondensation of 1-aryl-1-chloro-2,2,2-trifluoroethyl isocyanates with 3-amino-1-arylimino-1H-isoindoles

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Abstract

4-Trifluoromethyl-3,4-dihydro-1,3,5-triazino[2,1-a]isoindol-2-ones were prepared by reaction of 1-aryl-1-chloro-2,2,2-trifluoroethyl isocyanates with 3-amino-1-arylimino-1H-isoindoles in the presence of triethylamine. In some events alongside the main product isomeric 2-trifluoromethyl-2,3-dihydro-1,3,5-triazino[2,1-a]isoindol-4-ones were obtained. The regioselectivity of the reaction is affected by sterical and electronic characteristics of substituents and by temperature.

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Authors and Affiliations

  1. Taras Shevchenko Kiev National University, Kiev, 01033, Ukraine

    A. V. Biitseva, O. V. Gordienko & M. Yu. Kornilov

  2. Institute of Organic Chemistry, National Academy of Sciences of the Ukraine, Kiev, Ukraine

    V. A. Sukach & M. V. Vovk

  3. Research and Technology Enterprise “Institute of Single Crystals”, National Academy of Sciences of the Ukraine, Kiev, Ukraine

    O. V. Shishkin & V. V. D’yakonenko

Authors
  1. A. V. Biitseva
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  2. O. V. Gordienko
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  3. M. Yu. Kornilov
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  4. V. A. Sukach
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  5. M. V. Vovk
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  6. O. V. Shishkin
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  7. V. V. D’yakonenko
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Original Russian Text © A.V. Biitseva, O.V. Gordienko, M.Yu. Kornilov, V.A. Sukach, M.V. Vovk, O.V. Shishkin, V.V. D’yakonenko, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 2, pp. 271–277.

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Biitseva, A.V., Gordienko, O.V., Kornilov, M.Y. et al. Synthesis of 4-trifluoromethyl-3,4-dihydro-1,3,5-triazino[2,1-a]isoindol-2-ones by cyclocondensation of 1-aryl-1-chloro-2,2,2-trifluoroethyl isocyanates with 3-amino-1-arylimino-1H-isoindoles. Russ J Org Chem 43, 263–270 (2007). https://doi.org/10.1134/S1070428007020182

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  • DOI: https://doi.org/10.1134/S1070428007020182

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