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

Dhimant Desai; Jacek Krzeminski; Shantu Amin

doi:10.1021/tx00042a002

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

Dhimant Desai, Jacek Krzeminski, Shantu Amin

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2 Scopus citations

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 language	English (US)
Pages (from-to)	722-723
Number of pages	2
Journal	Chemical research in toxicology
Volume	7
Issue number	6
DOIs	https://doi.org/10.1021/tx00042a002
State	Published - Nov 1 1994

All Science Journal Classification (ASJC) codes

Toxicology

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10.1021/tx00042a002

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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",

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doi = "10.1021/tx00042a002",

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journal = "Chemical research in toxicology",

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

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