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Dimethylaminomethylene derivatives of S,S-dioxides of 1,4-benzothiazepin-3(2H)-one and 4,1-benzothiazepin-2(3H)-one: comparison of interaction with nucleophiles

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Abstract

Reactions of dimethylaminomethylene derivatives of 4,5-dihydro-1,4-benzothiazepin-3(2H)-one 1,1-dioxide and 1,5-dihydro-4,1-benzothiazepin-2(3H)-one 4,4-dioxide with O-nucleophile (hydroxide ion) and N-nucleophiles (aliphatic and aromatic amines, hydroxylamine, hydrazine, phenylhydrazines, N,N-dimethylhydrazine, amidines, and esters of amino acids) have been investigated. Compounds with a carbonyl group or a hydrogen at the nitrogen atom of the 1,4-benzothiazepine cycle are more reactive than N-Me derivatives. Products of transamination of 4,1-benzothiazepine derivatives have not been obtained, but hydrolysis led to the corresponding enol or 1,1-diol.

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Authors and Affiliations

  1. Department of Organic Chemistry, Taras Shevchenko Kyiv National University, 64 Volodymyrska str., Kiev, 01033, Ukraine

    Taras M. Tarasiuk, Tetiana A. Volovnenko & Yulian M. Volovenko

  2. STC “Institute for Single Crystals” National Academy of Science of Ukraine, 60 Lenina ave., Kharkiv, 61001, Ukraine

    Volodymyr V. Medviediev & Oleg V. Shishkin

  3. Department of Inorganic Chemistry, V. N. Karazin Kharkiv National University, 4 Svobody sq., Kharkiv, 61122, Ukraine

    Oleg V. Shishkin

Authors
  1. Taras M. Tarasiuk
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  2. Tetiana A. Volovnenko
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  3. Yulian M. Volovenko
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  4. Volodymyr V. Medviediev
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  5. Oleg V. Shishkin
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Correspondence to Taras M. Tarasiuk.

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Tarasiuk, T.M., Volovnenko, T.A., Volovenko, Y.M. et al. Dimethylaminomethylene derivatives of S,S-dioxides of 1,4-benzothiazepin-3(2H)-one and 4,1-benzothiazepin-2(3H)-one: comparison of interaction with nucleophiles. Monatsh Chem 145, 1987–1997 (2014). https://doi.org/10.1007/s00706-014-1290-x

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  • DOI: https://doi.org/10.1007/s00706-014-1290-x

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