Convenient synthesis of 3-methoxybenz[a]anthracene-7,12-dione

Chem Res Toxicol. 1994 Nov-Dec;7(6):722-3. doi: 10.1021/tx00042a002.

Abstract

The regioselective synthesis of 3-methoxybenz[a]anthracene-7,12-dione by oxidative photocyclization is described. The synthesis involved preparation of 1-(1-bromo-2-naphthyl)-2-(3- methoxyphenyl)ethylene by Wittig reaction, followed by photocyclization for 4 h. This gave 7-bromo-3-methoxybenz[a]anthracene. Extended photocyclization over 16 h under similar conditions gave 3-methoxybenz[a]anthracene-7,12-dione, an important intermediate in the synthesis of 7,12-dimethylbenz[a]anthracene-3,4-diol 1,2-epoxide.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Anthraquinones / chemical synthesis*
  • Anthraquinones / chemistry

Substances

  • Anthraquinones
  • 3-methoxybenzo(a)anthracene-7,12-dione