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2,1-Benzothiazine 2,2-Dioxides. 9*. Alkylation of Methyl 4-Hydroxy-1-Methyl-2,2-Dioxo-1Н-2λ6,1-Benzothiazine-3-Carboxylate with Ethyl Iodide

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Chemistry of Heterocyclic Compounds Aims and scope

The alkylation of methyl 4-hydroxy-1-methyl-2,2-dioxo-1Н-2λ6,1-benzothiazine-3-carboxylate in DMSO or acetone with ethyl iodide at 25°С gave a mixture of 3-ethyl- and 4-ethoxy-substituted derivatives, in complete agreement with quantum-chemical calculations. The ratio of С- and О-alkylation products changed depending on the alkali metal carbonate used as a base. The reaction practically did not proceed in anhydrous THF or water due to the low nucleophilicity of the anion.

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The authors would like to express their gratitude to Senior Researcher F. M. Dolgushin (A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow) for assistance with X-ray structural analysis.

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Authors and Affiliations

  1. National University of Pharmacy, 53 Pushkinska St., Kharkiv, 61002, Ukraine

    I. V. Ukrainets & L. A. Petrushova

  2. Institute of Single Crystals, National Academy of Sciences of Ukraine, 60 Lenin Ave., Kharkiv, 61001, Ukraine

    S. V. Shishkina

  3. Far Eastern State Medical University, 35 Murav’eva-Amurskogo St., Khabarovsk, 680000, Russia

    G. Sim

Authors
  1. I. V. Ukrainets
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  2. L. A. Petrushova
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  3. S. V. Shishkina
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  4. G. Sim
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Correspondence to I. V. Ukrainets.

Additional information

*For Communication 8, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1892-1899, December, 2014.

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Ukrainets, I.V., Petrushova, L.A., Shishkina, S.V. et al. 2,1-Benzothiazine 2,2-Dioxides. 9*. Alkylation of Methyl 4-Hydroxy-1-Methyl-2,2-Dioxo-1Н-2λ6,1-Benzothiazine-3-Carboxylate with Ethyl Iodide. Chem Heterocycl Comp 50, 1741–1747 (2015). https://doi.org/10.1007/s10593-015-1646-0

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