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Regio- and stereoselective N 2-functionalization with propanamide fragment of aromatic and heteroaromatic aldehydes thiosemicarbazones

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Abstract

Aiming at the synthesis of new potentially pharmacologically active compounds combining in the molecule structures of thiosemicarbazone and 3-hydrazinylpropionic acid, we performed a regio- and stereoselective N 2-functionalization of thiosemicarbazones of aromatic and heteroaromatic aldehydes by alkaline hydration of the corresponding (E)-N 2-cyanoethyl derivatives (propanenitriles) prepared by a regioand stereoselective cyanoethylation with acrylonitrile. The hydration proceeds with the retention of the Econfiguration of the initial propanenitriles.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    A. G. Mal’kina, V. V. Nosyreva, A. V. Afonin, A. I. Albanov & B. A. Trofimov

  2. Irkutsk Research Center of Surgery and Traumatology, Irkutsk, Russia

    Q. A. Apartsin & E. G. Grigor’ev

Authors
  1. A. G. Mal’kina
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  2. V. V. Nosyreva
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  3. A. V. Afonin
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  4. A. I. Albanov
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  5. Q. A. Apartsin
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  6. E. G. Grigor’ev
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  7. B. A. Trofimov
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Corresponding author

Correspondence to B. A. Trofimov.

Additional information

Original Russian Text © A.G. Mal’kina, V.V. Nosyreva, A.V. Afonin, A.I. Albanov, Q.A. Apartsin, E.G. Grigor’ev, B.A. Trofimov, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 8, pp. 1211–1216.

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Mal’kina, A.G., Nosyreva, V.V., Afonin, A.V. et al. Regio- and stereoselective N 2-functionalization with propanamide fragment of aromatic and heteroaromatic aldehydes thiosemicarbazones. Russ J Org Chem 53, 1226–1232 (2017). https://doi.org/10.1134/S1070428017080115

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  • DOI: https://doi.org/10.1134/S1070428017080115

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