A large-scale synthesis of the bioreductive drug 1, 4-bis {[2-(dimethylamino) ethyl] amino}-5, 8-dihydroxyanthracene-9, 10-dione bis-N-oxide (AQ4N)

HH Lee, WA Denny

Index: Lee, Ho H.; Denny, William A. Journal of the Chemical Society - Perkin Transactions 1, 1999 , # 19 p. 2755 - 2758

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Citation Number: 10

Abstract

A large-scale synthesis of the bis-bioreductive drug 1, 4-bis {[2-(dimethylamino) ethyl] amino}-5, 8-dihydroxyanthracene-9, 10-dione bis-N-oxide (AQ4N) has been developed. This six-step synthesis provides AQ4N in 20% overall yield from readily available tetrachlorophthalic anhydride. The key step was a KF–NaF-mediated conversion of 3, 6- dichlorophthalic anhydride to 3, 6-difluorophthalic anhydride, which could be achieved in ...