Oxidative free radical reactions between 2-amino-1,4-benzoquinones and carbonyl compounds

Che Ping Chuang, An I. Tsai

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

The manganese(III) initiated oxidative free radical reactions of 2-amino-1,4-benzoquinone are described. The free radical reaction of 5,6-dimethyl-2-methylamino-1,4-benzoquinone (1) provides a novel method for the synthesis of indole-4,7-dione and indole-2,4,7-trione. High chemoselectivity was observed in different solvents. The regioselectivity of this reaction was also studied with 5-methyl-2-methylamino-1,4-benzoquinone (19). In most cases, indole-4,7-diones 20 and 21 were produced in high regioselectivity.

Original languageEnglish
Pages (from-to)11911-11919
Number of pages9
JournalTetrahedron
Volume63
Issue number48
DOIs
Publication statusPublished - 2007 Nov 26

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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