Abstract
Chlorokojic acid was reacted with S2O3 2−, NO3 −, N3 −, I−, and SCN−. Only the three latter nucleophiles substituted the chlorine atom in the 2-CH2Cl group of kojic acid. In none of the products nucleophilic substitution at position 6 of the 4-pyrone could be found. Regular substituion of chlorokojic acid with I− (iodokojic acid), N3 − (azidokojic acid), and SCN− (thiocyanato and isothiocyanato kojic acids) was accompanied by formation of allomaltol. Reaction pathways for the formation of allomaltol and 6-substituted allomaltol derivatives are proposed. The latter has been formerly discovered in the reaction of chlorokojic acid with secondary amines.
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