THE INTERACTION OF o-DIPHENOLS WITH α-DIKETONES: THE REACTION OF 5,6-DIHYDROXY-N-METHYLINDOLE WITH DEHYDROASCORBIC ACID

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Abstract
5,6-Dihydroxy-N-methylmdole readily reacts with dehydroascorbic acid in aqueous solution at room temperature. The o-diphenol system of the indole derivative interacts with the α-diketone function of dehydroascorbic acid to form a 1,4-benzodioxane derivative. This type of reaction appears to be a general one since similar interactions occur between other o-diphenols and α-diketones. The mechanism by which the 1,4-benzodioxane derivative is obtained when adrenochrome is reduced with ascorbic acid is discussed.