Improved syntheses of 6??hydroxy??5??methoxy??and 5??hydroxy??6??methoxyindoles and their O??acetates, analogs of natural eumelanin precursors

CB Rogers, CA Blum, BP Murphy

Index: Rogers, C. Bradford; Blum, Charles A.; Murphy, Bryan P. Journal of Heterocyclic Chemistry, 1987 , vol. 24, p. 941 - 943

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Citation Number: 9

Abstract

Abstract Improved routes for syntheses of gram quantities of the isomeric 5, 6- acetoxymethoxyindoles, and milligram amounts of the 5, 6-hydroxymethoxyindoles, have been developed. They depend on regiospecific nitration of the benzyl ethers of vanillin and isovanillin as the first steps. Improved condensations of 4, 5-acetoxymethoxy-2- nitrobenzaldehydes with nitromethane gave 4, 5-acetoxymethoxy-2, β-dinitrostyrenes as ...