A novel oxidative free radical reaction between 2-amino-1,4-benzoquinones and benzoylacetonitriles

Che Ping Chuang, An I. Tsai

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

The manganese(III) initiated oxidative free radical reaction between 2-amino-1,4-benzoquinones and benzoylacetonitriles is described. This free radical reaction provides a novel method for the synthesis of spirodione 3 and spirolactone 4. With 5,6-dimethyl-2-methylamino-1,4-benzoquinone, spirodione 3 was obtained exclusively. On the contrary, with 5-methyl-2-methylamino-1,4-benzoquinone, spirolactone 4 was produced in high chemo- and regioselectivity. By heating with sodium acetate, spirodione 3 can be converted to 4 effectively.

Original languageEnglish
Pages (from-to)9712-9717
Number of pages6
JournalTetrahedron
Volume63
Issue number39
DOIs
Publication statusPublished - 2007 Sep 24

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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