Статья
2018

Electrochemical Synthesis of 2-(2-Chlorophenyl)-2-[(3,4- dihydroxyphenyl)(methyl)amino]cyclohexanone


M. Najafi M. Najafi , M. M. Lajvardi M. M. Lajvardi , L. Youseftabar-Miri L. Youseftabar-Miri , M. Ameri M. Ameri , O. Ghaderi O. Ghaderi
Российский электрохимический журнал
https://doi.org/10.1134/S1023193518130311
Abstract / Full Text

Electrochemical oxidation of catechol has been studied in the presence of ketamine as a drug in phosphate buffer solution mixed with ethanol using voltammetric techniques. The obtained results indicated that the o-quinone formed from electro-oxidation of catechol participated in a 1,4-Michael addition reaction to form the corresponding new 2-(2-chlorophenyl)-2-[(3,4-dihydroxyphenyl)(methyl)amino]cyclohexanone under ECE mechanism. The electro-organic synthesis has been successfully performed under mild condition in a divided cell in good yield.

Author information
  • Department of Chemistry, Faculty of Science, Imam Hossein University, Tehran, 16597, Iran

    M. Najafi

  • Khatam Al-Anbia University, Tehran, Iran

    M. M. Lajvardi

  • Department of Chemistry, Tehran Medical Sciences Branch, Islamic Azad University, Tehran, Iran

    L. Youseftabar-Miri

  • Department of Chemistry, Semnan University, Semnan, Iran

    M. Ameri & O. Ghaderi

References
  1. Patai, S., The Chemistry of the Quinonoid Compounds, Parts 1, 2, New York: Wiley, 1974.
  2. Komiyama, T., Kikuchi, T., and Sugiura, Y., Interactions of anticancer quinone drugs, aclacinomycin A, adriamycin, carbazilquinone, and mitomycin C, with NADPH-cytochrome P-450 reductase, xanthine oxidase and oxygen, J. Pharmacobio-dyn., 1986, vol. 9, p. 651.
  3. Hijazi, Y. and Boulieu, R., Contribution of CYP3A4, CYP2B6, and CYP2C9 isoforms to N-demethylation of ketamine in human liver microsomes, Drug Metab. Dispos., 2002, vol. 30, p. 853.
  4. Peck, T.E., Hill, S.A., and Williams, M., Pharmacology for Anaesthesia and Intensive Care, 3rd ed., Cambridge: Cambridge University Press, 2008.
  5. Bergman, S.A., Ketamine: review of its pharmacology and its use in pediatric anesthesia, Anesth. Prog., 1999, vol. 46, p. 10.
  6. Asghari, A., Ghaderi, O., Ameri, M., Rajabi, M., and Bakherad M., Clean and catalyst-less electrosynthesis of benzofurans via p-phenylenediamine oxidation in the presence of barbiturics, J. Electrochem. Soc., 2015, vol. 162, p. G14.
  7. Elinson, M.N., Vereshchagin, A.N., and Ryzhkov, F.V., Catalysis of cascade and multicomponent reactions of carbonyl compounds and C–H acids by electricity, Chem. Rec., 2016, vol. 16, p. 1950.
  8. Ameri, M., Asghari, A., Amoozadeh, A., Bakherad, M., and Nematollahi, D., Facile and one-pot, electroorganic synthesis of a new bis-quinone by the ECCE mechanism in green media, Chin. Chem. Lett., 2014, vol. 25, p. 1607.
  9. Ameri, M., Asghari, A., Amoozadeh, A., Bakherad, M., and Nematollahi, D., Green and highly efficient synthesis of new bis-benzofurans via electrochemical methods under ECECCC mechanism, J. Electrochem. Soc., 2014, vol. 161, p. G75.
  10. Nematollahi, D., Tammari, E., Sharifi, S., and Kazemi, M., Mechanistic study of the oxidation of catechol in the presence of secondary amines by digital simulation of cyclic voltammograms, Electrochim. Acta, 2004, vol. 49, p. 591.
  11. Chamjangali, M.A., Bakherad, M., and Ameri, M., Electrochemical oxidation of catechol derivatives in the presence of 3-acetyldihydro-2 (3H)-furanone: efficient and green method for synthesis of new butyrolactone derivatives, Monatsh. Chem., 2014, vol. 146, p. 111.
  12. Bard, A.J., Electrochemical Methods, 2nd ed., New York: Wiley, 2001, p. 103.
  13. Korotaeva, L.M., Kurmaz, V.A., Rubinskaya, T.Ya., and Gul’tyai, V.P., Electrochemical behavior of cinnamic acid associates on carbosital electrode in dimethylformamide in the presence of external proton donors, Russ. J. Electrochem., 2015, vol. 51, p. 113.
  14. Nematollahi, D. and Hesari, M., Electrochemical synthesis of amino-substituted 1,2-benzoquinone derivatives, J. Electroanal. Chem., 2005, vol. 577, p. 197.