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<p>Alkylation of aniline with bicyclic monoterpenes, namely, (−)-β- and (+)-α-pinenes, in the presence of various catalysts was studied. Aluminum-containing catalysts were found to be efficient for the synthesis of <i>N</i>-substituted anilines with the <i>p</i>-menthene and bornyl structure of the terpene substituent. The reactions of α-pinene with an excess of aniline gave rise to substituted tetrahydroquinolines. Using various test systems, it was shown that the antioxidant activity of terpenylanilines significantly depends on the isomerism of the terpene fragment. <i>N</i>-Bornylaniline was found to be more active than <i>N</i>-alkylaniline with a <i>p</i>-menthene fragment, which makes it of interest for further, more detailed study as a new highly active antioxidant for technical and biomedicinal applications.</p>

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Synthesis and comparative evaluation of antioxidant properties of aniline N-derivatives containing p-menthene and bornyl fragments

  • 期刊论文

  • 发表日期：

    2025年11月1日

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  • I. Yu. Chukicheva,
  • O. A. Shumova,
  • O. G. Shevchenko,
  • A. V. Kutchin

摘要

Alkylation of aniline with bicyclic monoterpenes, namely, (−)-β- and (+)-α-pinenes, in the presence of various catalysts was studied. Aluminum-containing catalysts were found to be efficient for the synthesis of N-substituted anilines with the p-menthene and bornyl structure of the terpene substituent. The reactions of α-pinene with an excess of aniline gave rise to substituted tetrahydroquinolines. Using various test systems, it was shown that the antioxidant activity of terpenylanilines significantly depends on the isomerism of the terpene fragment. N-Bornylaniline was found to be more active than N-alkylaniline with a p-menthene fragment, which makes it of interest for further, more detailed study as a new highly active antioxidant for technical and biomedicinal applications.