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Oxidation of N-acyl-2-(cycloalk-1-enyl)anilines with ozone and hydrogen peroxide

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Abstract

Treatment of the ozonization products from N-acetyl- or 2-methyl-N-trifluoroacetyl-6-(cyclopent-1-enyl)anilines with NaBH4 gives 6-methyl-2-tetrahydropyranylaniline. When treated with Me2S, the ozonization products yield the corresponding oxoaldehyde dimethyl acetals. The oxidation of N-acetyl-2-(cyclopent-1-enyl)- or -(cyclohex-1-enyl)anilines with H2O2 in HCOOH affords ω-(2-acetamidophenyl)-5-oxopentanoic or -6-oxohexanoic acid, respectively. The reaction of N-acetyl-2-(cyclopent-1-enyl)aniline with H2O2 in the presence of Na2WO4 and H3PO4 gives 3,1-benzooxazine in high yield.

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Authors and Affiliations

  1. Ufa Research Center of the Russian Academy of Sciences, Institute of Organic Chemistry, 69 prosp. Oktyabrya, 450054, Ufa, Russian Federation

    R. R. Gataullin, A. A. Fatykhov, O. V. Shitikova, L. V. Spirikhin & I. B. Abdrakhmanov

  2. Ufa State University of Petroleum Technology, 1 ul. Kosmonavtov, 450062, Ufa, Russian Federation

    M. F. Nasyrov

  3. Bashkir State Agricultural University, 34 ul. 50-letiya Oktyabrya, 450003, Ufa, Russian Federation

    D. I. D"yachenko

Authors
  1. R. R. Gataullin
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  2. M. F. Nasyrov
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  3. D. I. D"yachenko
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  4. A. A. Fatykhov
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  5. O. V. Shitikova
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  6. L. V. Spirikhin
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  7. I. B. Abdrakhmanov
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Gataullin, R.R., Nasyrov, M.F., D"yachenko, D.I. et al. Oxidation of N-acyl-2-(cycloalk-1-enyl)anilines with ozone and hydrogen peroxide. Russian Chemical Bulletin 51, 124–127 (2002). https://doi.org/10.1023/A:1015074016576

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  • DOI: https://doi.org/10.1023/A:1015074016576

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