1,2-Acyl group migration in the oxidative free radical reaction of 2-substituted-1,4-quinones

An I. Tsai, Che Ping Chuang

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16 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)5098-5102
Number of pages5
Issue number22
Publication statusPublished - 2008 May 26

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


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