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Synlett 1997; 1997(2): 161-162
DOI: 10.1055/s-1997-752
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Oxidation of 1-Tetralone Oximes with 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in Non-aqueous AcOH-Benzene Media: Easy and Efficient Preparation of Naphthoquinone Monooximes

Toshiko Watanabe* , Yumie Oku, Hisashi Ishii, Tsutomu Ishikawa
  • *Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage, Chiba, 263, Japan, Fax +81-43-255-1574; E-mail toshiw@p.chiba-u.ac.jp
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Publication Date:
31 December 2000 (online)

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2-Aryl-1,4-naphthoquinone 1-monooximes, key intermediates to O6-benzo[c]phenanthridine alkaloids, were prepared from 2-aryl-1-tetralones via oximes by an oxygenation-dehydrogenation reaction with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in non-aqueous AcOH-benzene media in high yield.

benzo[c]phenanthridine - 2-aryl-1-tetralone - naphthoquinone monooxime - DDQ oxidation