Convenient Synthesis of 3-Methoxybenz[a]anthracene-7,12-dione

Research output: Contribution to journalArticle

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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.

Original languageEnglish (US)
Pages (from-to)722-723
Number of pages2
JournalChemical Research in Toxicology
Volume7
Issue number6
DOIs
StatePublished - Nov 1 1994

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Epoxy Compounds
anthracene
ethylene

All Science Journal Classification (ASJC) codes

  • Toxicology

Cite this

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title = "Convenient Synthesis of 3-Methoxybenz[a]anthracene-7,12-dione",
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.",
author = "Dhimant Desai and Jacek Krzeminski and Shantu Amin",
year = "1994",
month = "11",
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journal = "Chemical Research in Toxicology",
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}

Convenient Synthesis of 3-Methoxybenz[a]anthracene-7,12-dione. / Desai, Dhimant; Krzeminski, Jacek; Amin, Shantu.

In: Chemical Research in Toxicology, Vol. 7, No. 6, 01.11.1994, p. 722-723.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Convenient Synthesis of 3-Methoxybenz[a]anthracene-7,12-dione

AU - Desai, Dhimant

AU - Krzeminski, Jacek

AU - Amin, Shantu

PY - 1994/11/1

Y1 - 1994/11/1

N2 - 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.

AB - 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.

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