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Oxidation of N-acyl-2-(cycloalk-1-enyl)anilines with ozone and hydrogen peroxide |
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| Authors: | Gataullin R R Nasyrov M F D"yachenko D I Fatykhov A A Shitikova O V Spirikhin L V Abdrakhmanov I B |
| Institution: | (1) Ufa Research Center of the Russian Academy of Sciences, Institute of Organic Chemistry, 69 prosp. Oktyabrya, 450054 Ufa, Russian Federation;(2) Ufa State University of Petroleum Technology, 1 ul. Kosmonavtov, 450062 Ufa, Russian Federation;(3) Bashkir State Agricultural University, 34 ul. 50-letiya Oktyabrya, 450003 Ufa, Russian Federation |
| 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  -(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. |
| Keywords: | 2-(cycloalk-1-enyl)anilines ozonization oxidation with hydrogen peroxide dimethyl acetals 6-methyl-2-(tetrahydropyranyl)aniline oxo acids 3 1-benzooxazines |
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