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Synthesis 1987; 1987(9): 790-794
DOI: 10.1055/s-1987-28075
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Synthesis of New Bicyclic Quinones: 2H-1-Benzopyran-5,8-quinones and Related Compounds

Olivia Reinaud* , Patrice Capdevielle, Michel Maumy
  • *Laboratoire de Recherches Organiques de l'ESPCI, associé au CNRS, 10 rue Vauquelin, F-75231 Paris Cedex 05, France
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Publication Date:
12 September 2002 (online)

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The synthesis of new 2H-1-benzopyran-5,8-quinones has been realized in three steps from p-methoxyphenol with 84-88% overall yield. It consists at first in a regioselective nucleophilic substitution of propargyl alcoholates on an appropriate 4,5-disubstituted o-quinone (obtained by copper-catalyzed oxidation of p-methoxyphenol) and subsequently in a thermal isomerization. Relative stabilities of title compounds are described, as well as several transformation products.

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