Manganese(III)-based oxidation of 2,4-piperidinediones in the presence of alkenes |
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Authors: | Kentaro Asahi |
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Affiliation: | a Graduate School of Science and Technology, Department of Science and Technology for Chemistry and Physics, Kumamoto University, Kurokami 2-39-1, Kumamoto 860 8555, Japan b Department of Science, Faculty of Science, Kumamoto University, Kurokami 2-39-1, Kumamoto 860 8555, Japan |
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Abstract: | The manganese(III)-catalyzed aerobic oxidation of 2,4-piperidinediones was performed in the presence of alkenes at room temperature, producing 1-hydroxy-8-aza-2,3-dioxabicyclo[4.4.0]decan-7-ones in excellent yields. On the other hand, the 6-acetoxy-3-aza-7-oxabicyclo[4.3.0]nonan-2-ones were obtained by the oxidation of the 2,4-piperidinedione-3-carboxylates with manganese(III) acetate in the presence of alkenes at elevated temperature under an argon atmosphere. A similar oxidation using decarboxylated 2,4-piperidinediones produced the 2,3,6,7-tetrahydrofuro[3,2-c]pyridin-4(5H)-ones and/or 2,3,6,7-tetrahydrofuro[2,3-b]pyridin-4(5H)-ones in good yields. The structure determination and the decomposition reaction of the azabicyclic peroxides in acetic acid or acetic anhydride, and the reaction pathway were also described. |
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Keywords: | Endoperoxides Aerobic oxidation Manganese(III) acetate 2,4-Piperidinediones Tetrahydrofuropyridinones |
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