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Abstract <p>A method was developed for the synthesis of a new amide derivative of phenothiazine containing a (4<i>RS</i>,8<i>RS</i>)-4,8,12-trimethyltridecane chain identical to the phytyl isoprenoid chain of racemic α-tocopherol. The phenothiazine analogue of alpha-tocopherol was obtained by coupling of 2-aminophenothiazine with (4<i>RS</i>,8<i>RS</i>)-4,8,12-trimethyltridecanoic acid. The main features of its synthesis were the Bayer–Villiger oxidation of phytone under the action of a household oxidant based on sodium percarbonate “O<sub>2</sub>Clean” and the environmentally friendly aerobic oxidation protocol of (4<i>RS</i>,8<i>RS</i>)-4,8,12-trimethyltridecanole with oxygen using the iron-containing catalyst Fe(NO<sub>3</sub>)<sub>3</sub>·9H<sub>2</sub>O–TEMPO–KCl.</p>

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Efficient and Practical Synthesis of a Novel Lipophilic Phenothiazine Derivative with an α-Tocopherol Isoprenoid Side Chain

  • 期刊论文

  • 发表日期：

    2025年6月1日

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  • A. Yu. Spivak,
  • D. A. Nedopekina,
  • E. V. Davletshin,
  • R. R. Khalitova

摘要

Abstract

A method was developed for the synthesis of a new amide derivative of phenothiazine containing a (4RS,8RS)-4,8,12-trimethyltridecane chain identical to the phytyl isoprenoid chain of racemic α-tocopherol. The phenothiazine analogue of alpha-tocopherol was obtained by coupling of 2-aminophenothiazine with (4RS,8RS)-4,8,12-trimethyltridecanoic acid. The main features of its synthesis were the Bayer–Villiger oxidation of phytone under the action of a household oxidant based on sodium percarbonate “O2Clean” and the environmentally friendly aerobic oxidation protocol of (4RS,8RS)-4,8,12-trimethyltridecanole with oxygen using the iron-containing catalyst Fe(NO3)3·9H2O–TEMPO–KCl.