Formation of isoxazole derivatives via nitrile oxide using ammonium cerium nitrate (CAN): a novel one-pot synthesis of 3-acetyl- and 3-benzoylisoxazole derivatives |
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Authors: | Ken-ichi Itoh |
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Institution: | Department of Chemistry, Rikkyo (St Paul's) University, 3-34-1 Nishi-Ikebukuro, Toshima-ku, 171-8501 Tokyo, Japan |
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Abstract: | The reactions of alkenes and alkynes with ammonium cerium(IV) nitrate ((NH4)2Ce(NO3)6, CAN(IV)) in acetone under reflux gave the corresponding 3-acetyl-4,5-dihydroisoxazole and 3-acetylisoxazole derivatives. In the case of acetophenone, 3-benzoyl-4,5-dihydroisoxazole and 3-benzoylisoxazole derivatives were obtained. Reaction of acetone with CAN(IV) afforded the corresponding furoxan (3,4-diacetyl-1,2,5-oxadiazole 2-oxide) as the dimer of nitrile oxide. Moreover, it was found that yields of isoxazole derivatives were improved using ammonium cerium(III) nitrate tetrahydrate ((NH4)2Ce(NO3)5·4H2O, CAN(III))-formic acid. The reaction mechanisms based on nitration and formation of nitrile oxide mediated by CAN(IV) or CAN(III) from acetone or acetophenone are also proposed. |
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Keywords: | Ammonium cerium(IV) nitrate Ammonium cerium(III) nitrate Formic acid Isoxazole derivatives Nitrile oxide |
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