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Synthesis of a series of tetraminic acid sulfone analogs

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Abstract

We have introduced a strategy for the construction of spirocycloalkane 1λ6-isothiazolidine-1,1,4-triones through the mesylation of 1-aminocyclopentane-, 1-aminocyclohexane-, and 1-aminocycloheptanecarboxylic acid esters with methanesulfonylchloride followed by alkylation with methyl iodide and consequent cyclization in the presence of potassium tert-butoxide in N,N-dimethylformamide. The spirocycloalkane 4-amino-2,3-dihydro-1H-1λ6-isothiazole-1,1-diones were prepared via mesylation of N-methylated 1-aminocyclopentyl-, 1-aminocyclohexyl-, and 1-aminocycloheptyl carbonitriles followed by treatment of obtained N-(1-cyanocycloalkyl)-N-methylmethanesulfonamides with potassium tert-butoxide in N,N-dimethylformamide. The spiro 4-amino-2,3-dihydro-1H-1λ6-isothiazole-1,1-diones were converted into the target spiro 1λ6-isothiazolidine-1,1,4-triones by acid-catalyzed hydrolysis. The structure of a target spiro compound and its isolated key intermediate was confirmed by X-ray diffraction study. The interaction of spiro 1λ6-isothiazolidine-1,1,4-triones with N,N-dimethylformamide dimethyl acetal leads to the formation of spiro 5-[(Z)-(dimethylamino)methylidene]-1λ6-isothiazolidine-1,1,4-triones.

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Acknowledgements

We would also like to show our gratitude to Kitty Dobrydneva for sharing her pearls of wisdom with us during the course of this research, and we thank “anonymous” reviewers for their so-called insights.

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Authors and Affiliations

  1. Chemistry Department, Taras Shevchenko National University of Kiev, Lva Tolstoho Street 12, Kiev, 01033, Ukraine

    Maria V. Popova, Alexey V. Dobrydnev, Maksim S. Dyachenko & Yulian M. Volovenko

  2. Enamine Ltd., Alexandra Matrosova Street 23, Kiev, 01103, Ukraine

    Maria V. Popova & Maksim S. Dyachenko

  3. UPR CNRS 8241, LCC, 205 route de Narbonne, 31077, Toulouse, France

    Carine Duhayon & Dymytrii Listunov

Authors
  1. Maria V. Popova
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  2. Alexey V. Dobrydnev
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  3. Maksim S. Dyachenko
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  4. Carine Duhayon
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  5. Dymytrii Listunov
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  6. Yulian M. Volovenko
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Correspondence to Alexey V. Dobrydnev.

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Popova, M.V., Dobrydnev, A.V., Dyachenko, M.S. et al. Synthesis of a series of tetraminic acid sulfone analogs. Monatsh Chem 148, 939–946 (2017). https://doi.org/10.1007/s00706-016-1884-6

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  • DOI: https://doi.org/10.1007/s00706-016-1884-6

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