Oxidative free radical cyclization of 2-(ethoxycarbonylmethyl)-1,4- naphthoquinone derivatives

Hui Li Chen, Chien Yu Lin, Yu Chih Cheng, An I. Tsai, Che Ping Chuang

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

A manganese(III)-mediated oxidative free radical cyclization of 2-(ethoxycarbonylmethyl)-1,4-naphthoquinone derivatives is described. These starting 2-(ethoxycarbonylmethyl)-1,4-naphthoquinones can be synthesized effectively from the reaction of corresponding 1,4-naphthoquinones with ethyl nitroacetate. With 2-benzyl-3-(ethoxycarbonylmethyl)-1,4-naphthoquinones, naphthacene-5,12-diones were produced effectively in high selectivity. With ethyl 2-benzoyl-3-(ethoxycarbonylmethyl)-1,4-naphthoquinones, in addition to the expected 6-hydroxynaphthacene-5,12-diones, the novel naphtho[2,3-c]furan-4,9- diones were also formed as the major product.

Original languageEnglish
Pages (from-to)977-985
Number of pages9
JournalSynthesis
Issue number6
DOIs
Publication statusPublished - 2005 Apr 18

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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