Abstract
1,3-Dipolar cycloaddition of benzonitrile and m-nitrobenzonitrile oxides to the enol form of dimedone gives the corresponding 4-oxotetrahydrobenzisoxazoles. A second reaction path — nucleophilic addition of the enol to the N-oxide to give a hydroxamic acid derivative — is observed in the case of m-nitrobenzonitrile oxide. The tetrahydrobenzisoxazoles are converted to enamine derivatives of benzoyldimedone under catalytic hydrogenation conditions.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 901–904, July, 1974.
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Akhrem, A.A., Khripach, V.A. & Lakhvich, F.A. Reaction of some aromatic nitrile oxides with dimedone. Chem Heterocycl Compd 10, 784–787 (1974). https://doi.org/10.1007/BF00471353
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DOI: https://doi.org/10.1007/BF00471353