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1,3-Dipolar cycloadditions of heterocycles. 23. Cycloadditions of benzonitrile oxides to N-(2,6-dialkylphenyl)maleinimides

M. Konopíková, Ľ. Fišera, I. Goljer, Š. Varkonda, O. Hýblová, E. Šturdík, and R. Ujhélyová

Department of Organic Chemistry, Faculty of Chemical Technology, Slovak Technical University, CS-81237 Bratislava

 

Abstract: The paper describes 1, 3-dipolar cycloaddition of substituted benzonitrile oxides and N-(2, 6-dialkylphenyl)maleinimides, giving 3, 5-diaryl-4, 6-dioxo-3a, 4, 6, 6a-tetrahydropyrrolo[3,4-d]isoxazoles. The prepared isoxazoles showed activity against bacteria, yeasts, and moulds. The reaction of N-(2-ethyl-6-methylphenyl)maleinimide with nitrile oxide gave, due to hindered rotation, two diastereomers characterized by different spatial arrangement of alkyl groups vs. bridgehead hydrogen atoms.

Full paper in Portable Document Format: 456a789.pdf

 

Chemical Papers 45 (6) 789–805 (1991)

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