1,2-Acyl group migration in the oxidative free radical reaction of 2-substituted-1,4-quinones |
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Authors: | An-I Tsai |
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Institution: | Department of Chemistry, National Cheng Kung University, Tainan 70101, Taiwan |
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Abstract: | Oxidative free radical reactions of 2-substituted-1,4-quinone derivatives are described. Electrophilic carbon-centered radical produced by the manganese(III) acetate oxidation of α-chloro-β-ketoester undergoes efficient addition to the C-C double bond of 5,6-dimethyl-2-(methylamino)-1,4-benzoquinone, and this reaction provides a novel method for the synthesis of spirolactam 3 and indole-2,4,7-trione 4. It shows high chemoselectivity depending on the migratory aptitude of the substituent on α-chloro-β-ketoester. Imine radical can be generated from the oxidation of β-enamino carbonyl compound with Mn(III) or Ce(IV) salt. With 2-hydroxy-1,4-naphthoquinone, spirolactam 6 was prepared from β-enamino carbonyl compound effectively. TBACN/CHCl3 is the most effective reaction condition for the formation of 6. |
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Keywords: | 5 6-Dimethyl-2-(methylamino)-1 4-benzoquinone α-Chloro-β-ketoester 2-Hydroxy-1 4-naphthoquinone β-Enamino carbonyl compound Spirolactam |
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