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l-Isoleucine-catalyzed Michael Synthesis of N-Alkylsuccinimide Derivatives and Their Antioxidant Activity Assessment

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Abstract

N-Substituted succinimides having different alkyl groups were prepared by the reaction of N-substituted maleimide with aldehydes. A two-component catalyst system composed of an amino acid (l-isoleucine) and a base (KOH) was used to facilitate reaction of the α-hydrogen-containing aldehyde with N-substituted maleimide. With 20 mol % catalyst/cocatalyst, good results in term of the reaction time and yield (892-99%) of products containing contiguous quaternary and tertiary stereogenic centers were obtained. The CHN elemental analyses of N-substituted succinimides indicated appreciable purity. Structural assessment of the synthesized N-substituted succinimides was carried out by 1H and 13C NMR spectroscopy. The products exhibited excellent antioxidant and mild antimicrobial activities.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Physical Sciences, Kohat University of Science and Technology, 26000, Kohat, KP, Pakistan

    A. Bibi, T. Shah & N. Khalid

  2. Department of Pharmacy, Faculty of Biological Sciences, University of Malakand, 18000, Chakdara Lower Dir, KP, Pakistan

    A. Sadiq & F. Ullah

  3. Department of Chemistry, Faculty of Physical Sciences, Quaid-i-Azam University, 45320, Islamabad, Pakistan

    A. Iqbal

Authors
  1. A. Bibi
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  2. T. Shah
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  3. A. Sadiq
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  4. N. Khalid
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  5. F. Ullah
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  6. A. Iqbal
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Correspondence to A. Bibi.

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Bibi, A., Shah, T., Sadiq, A. et al. l-Isoleucine-catalyzed Michael Synthesis of N-Alkylsuccinimide Derivatives and Their Antioxidant Activity Assessment. Russ J Org Chem 55, 1749–1754 (2019). https://doi.org/10.1134/S1070428019110174

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  • DOI: https://doi.org/10.1134/S1070428019110174

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