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Chemistry of Heterocyclic Compounds

, Volume 50, Issue 12, pp 1741–1747 | Cite as

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

  • I. V. UkrainetsEmail author
  • L. A. Petrushova
  • S. V. Shishkina
  • G. Sim
Article

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.

Keywords

ambident anions 4-hydroxy-2,1-benzothiazines alkylation keto-enol tautomerism 

Notes

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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Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • I. V. Ukrainets
    • 1
    Email author
  • L. A. Petrushova
    • 1
  • S. V. Shishkina
    • 2
  • G. Sim
    • 3
  1. 1.National University of PharmacyKharkivUkraine
  2. 2.Institute of Single CrystalsNational Academy of Sciences of UkraineKharkivUkraine
  3. 3.Far Eastern State Medical UniversityKhabarovskRussia

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