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Paper | Special issue | Vol 40, No. 1, 1995, pp.413-424
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S66
1,3-Dipolar Cycloaddition of Nitrile Oxides to 1,4-Naphthoquinone Derivatives

Francisco Fariña, M. Victoria Martín, Marta Muñoz, M. Carmen Paredes, and Raquel Rodoríguez

*Instituto de Química Médica, C. S. I. C., Calle Juan de Cierva, 3, 28006 Madrid, Spain


The 1,3-dipolar cycloadditions of benzonitrile and bromoformonitrile oxides (4 and 5) to naphthoquinone derivatives (3) proceed across the C=C double bond to afford naphthoisoxazolinediones. In the reaction with benzonitrile oxide (4) the initial cycloadducts (6 and 7) were isolated in good yields. However, the cycloaddition of bromoformonitrile oxide (5) affords directly the corresponding aromatized naphthoisoxazolediones (10 and 11) in good yields.