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Alkylation of 3-Trifluoromethyl-1,2-dihydroquinoxalin-2-one

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Abstract

O and N centers of 3-trifluoromethyl-1,2-dihydroquinoxalin-2-one anion shows in reactions with haloalkanes an ambident nucleophilic character. The chemoselectivity of the reaction depends on the alkylating agent: the methylation of 3-trifluoromethyl-1,2-dihydroquinoxalin-2-one in acetonitrile in the presence of K2CO3 yields only an N-methyl isomer whereas under the same conditions in the reaction with (4-bromobutyl)-acetate О- and N-alkylations are competing.

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Authors and Affiliations

  1. Postovskii Institute of Organic Synthesis, Ural branch, Russian Academy of Sciences, ul. S. Kovalevskoi/Akademicheskaya 22/20, Yekaterinburg, 620990, Russia

    A. E. Ivanova, Ya. V. Burgart, M. G. Pervova & V. I. Saloutin

  2. Ufa Institute of Chemistry, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, Bashkortostan, 450054, Russia

    S. S. Borisevich & S. L. Khursan

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  1. A. E. Ivanova
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Correspondence to V. I. Saloutin.

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Original Russian Text © A.E. Ivanova, Ya.V. Burgart, M.G. Pervova, S.S. Borisevich, S.L. Khursan, V.I. Saloutin, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 11, pp. 1687–1694.

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Ivanova, A.E., Burgart, Y.V., Pervova, M.G. et al. Alkylation of 3-Trifluoromethyl-1,2-dihydroquinoxalin-2-one. Russ J Org Chem 54, 1702–1709 (2018). https://doi.org/10.1134/S1070428018110131

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  • DOI: https://doi.org/10.1134/S1070428018110131

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