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Sulfo-Biginelli reaction: an insight into interaction between sulfamides and enolizable ketones

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Chemistry of Heterocyclic Compounds Aims and scope

The interaction employing sulfamide and enolizable ketones was closely inspected in Biginelli reaction. The three-component variation of the reaction ''sulfamide + ketone + anisaldehyde'' and ''sulfamide + ketone + N,N-diethylacetoacetamide'' featured a lack of selectivity and provided a mixture of possible condensation products. Selectivity was improved when ketones were used in the reaction both as carbonyl and enol components. It was shown that trimethylsilyl chloride promoted interaction of sulfamide with ketones to afford 1,2,6- thiadiazines. Limitations were noted and unpredictable outcomes of the reaction were discussed as well.

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Authors and Affiliations

  1. Enamine Ltd, 78 Winston Churchill St, Kyiv, 02094, Ukraine

    Alexander Yu. Lyapunov, Andriy V. Tarnovskiy, Dmitry A. Lega, Dmitriy M. Volochnyuk & Sergey V. Ryabukhin

  2. Taras Shevchenko National University of Kyiv, 60 Volodymyrska St, Kyiv, 01033, Ukraine

    Alexander Yu. Lyapunov, Andriy V. Tarnovskiy, Mariia H. Osokina, Galyna P. Grabchuk, Dmitriy M. Volochnyuk & Sergey V. Ryabukhin

  3. State Scientific Institution “Institute for Single Crystals”, National Academy of Sciences of Ukraine, 60 Nauky Ave, Kharkiv, 61072, Ukraine

    Svitlana V. Shishkina

  4. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St, Kyiv, 02660, Ukraine

    Svitlana V. Shishkina, Dmitriy M. Volochnyuk & Sergey V. Ryabukhin

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

    Dmitry A. Lega

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  1. Alexander Yu. Lyapunov
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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(6/7), 500–507

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Lyapunov, A.Y., Tarnovskiy, A.V., Osokina, M.H. et al. Sulfo-Biginelli reaction: an insight into interaction between sulfamides and enolizable ketones. Chem Heterocycl Comp 59, 500–507 (2023). https://doi.org/10.1007/s10593-023-03222-x

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