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Synlett 1990; 1990(6): 355-357
DOI: 10.1055/s-1990-21093
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Direct Oxidation of 1-Naphthaldehydes to 2-Substituted 1,4-Naphthoquinones: Application to the Chemoselective Syntheses of Pyrano- and Furano-1,2-naphthoquinones

R. B. Gupta* , R. W. Franck
  • *Chemistry Department, Hunter College, 695 Park Avenue, New York, NY 10021, USA
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Publication Date:
08 March 2002 (online)

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The oxidation of 1-naphthaldehydes, easily obtainable from the cycloaddition of isoquinolinium salts with vinyl ethers, using 30% hydrogen peroxide and 3N hydrochloric acid provides an efficient route for the preparation of 2-substituted 1,4-naphthoquinones. The 3-(3-hydroxypropyl) and 3-(2-hydroxyethyl) derivatives can be further elaborated to give 5,6-dioxo-3,4,5,6-tetrahydro-2H-naphtho[1,2-b]pyran and 4,5-dioxo-2,3,4,5-tetrahydronaphtho[1,2-b]furan respectively

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