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Synthesis 1993; 1993(3): 315-318
DOI: 10.1055/s-1993-25856
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One-Pot Preparation of 3-(2-Oxoalkyl)-1,2-naphthoquinones by Photochemical Reaction of 1,2-Naphthoquinones with Enol Ethers

Akio Takuwa* , Hidetoshi Iwamoto, Yutaka Nishigaichi, Kiyoshi Yamanaka
  • *Department of Chemistry, Faculty of Science, Shimane University, Matsue 690, Japan
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Publikationsdatum:
17. September 2002 (online)

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3-(2-Oxoalkyl)-1,2-naphthoquinones were synthesized facilely by photochemical reaction of 1,2-naphthoquinones with 2-methoxy-1-alkenes and subsequent oxidation of the photoadducts in one pot. Similarly, 3-phenacyl-, 3-formylmethyl- and 3-ethoxycarbonyl-methyl-1,2-naphthoquinones were obtained in excellent to good yields by reaction of 1,2-naphthoquinones with α-methoxystyrene, ethyl vinyl ether and 1,1-diethoxyethene, respectively.