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Abstract <p>5-[2-(<i>N</i>-Tosylamino)phenyl]-5-oxopentanoic acid was obtained by ozonation of <i>N</i>-tosyl-2-(cyclopent-1-en-1-yl)aniline followed by treatment of the reaction mixture with hydrogen peroxide in the presence of selenium dioxide. The reaction of the ozonation product of <i>N</i>-mesyl-2-(cyclohex-1-en-1-yl)aniline with hydroxylamine hydrochloride in isopropyl alcohol afforded 6-{2-[(methylsulfonyl)amino]phenyl}-6-oxohexanoic acid isopropyl ester, <i>N</i>-[2-(5-cyanopentanoyl)phenyl]methanesulfonamide, 6-(2-aminophenyl)-6-oxohexanoic acid <i>N</i>-mesylate and, presumably, <i>N</i>-mesyl-2-(2-oxocyclohex-1-yl)aniline in a ratio of 25 : 16 : 15 : 9. The corresponding oximes were obtained by reacting 5-[2-(<i>N</i>-tosylamino)phenyl]-5-oxopentanoic acid or 6-{2-[(methylsulfonyl)amino]phenyl}-6-oxohexanoic acid isopropyl ester with hydroxylamine. Further treatment of [(<i>N</i>-tosylamino)phenyl]oxopentanoic acid ketoxime with methanesulfonyl chloride in the presence of 2-aminopyridine yielded 3-(4-carboxypropyl-1)indazole <i>N</i>-tosylate. Under similar conditions, 5-(benzimidazole-2-yl)- and 5-(indazol-3-yl)pentanoic acid isopropyl ester <i>N</i>-mesylates were formed from the oxohexane homologue ketoxime in a ratio of approximately 5 : 1.</p>

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Ozonolysis Products of N-Mesyl- and N-Tosyl-2-(cycloalk-1-en-1-yl)anilines in the Synthesis of Benzo-Fused N,N-Heterocycles

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  • 发表日期：

    2025年6月1日

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  • R. R. Safargalin,
  • R. R. Gataullin

摘要

Abstract

5-[2-(N-Tosylamino)phenyl]-5-oxopentanoic acid was obtained by ozonation of N-tosyl-2-(cyclopent-1-en-1-yl)aniline followed by treatment of the reaction mixture with hydrogen peroxide in the presence of selenium dioxide. The reaction of the ozonation product of N-mesyl-2-(cyclohex-1-en-1-yl)aniline with hydroxylamine hydrochloride in isopropyl alcohol afforded 6-{2-[(methylsulfonyl)amino]phenyl}-6-oxohexanoic acid isopropyl ester, N-[2-(5-cyanopentanoyl)phenyl]methanesulfonamide, 6-(2-aminophenyl)-6-oxohexanoic acid N-mesylate and, presumably, N-mesyl-2-(2-oxocyclohex-1-yl)aniline in a ratio of 25 : 16 : 15 : 9. The corresponding oximes were obtained by reacting 5-[2-(N-tosylamino)phenyl]-5-oxopentanoic acid or 6-{2-[(methylsulfonyl)amino]phenyl}-6-oxohexanoic acid isopropyl ester with hydroxylamine. Further treatment of [(N-tosylamino)phenyl]oxopentanoic acid ketoxime with methanesulfonyl chloride in the presence of 2-aminopyridine yielded 3-(4-carboxypropyl-1)indazole N-tosylate. Under similar conditions, 5-(benzimidazole-2-yl)- and 5-(indazol-3-yl)pentanoic acid isopropyl ester N-mesylates were formed from the oxohexane homologue ketoxime in a ratio of approximately 5 : 1.