64831-67-0Relevant academic research and scientific papers
REGIOSELECTIVE REACTIONS OF 9-HYDROXY-10-CHLORO-1,4-ANTHRAQUINONE. SYNTHESIS OF DIGITOPURPONE AND ISLANDICIN
Gorelik, M. V.,Arinich, L. V.,Kotlyarevskii, O. I.,Fes'kova, E. A.
, p. 129 - 138 (2007/10/02)
9-Hydroxy-10-chloro-1,4-anthraquinone, obtained in the reaction of 1,4-dihydroxy-9,10-anthraquinone with thionyl chloride, is nitrated selectively at the peri position to the chlorine atom and is converted into 5-nitro-9-hydroxy-10-chloro-1,4-anthraquinone.The isomeric 8-nitro-9-hydroxy-10-chloro-1,4-anthraquinone is formed during the hydrolysis of the nitration product and the subsequent reaction of 5-nitro-1,4-dihydroxy-9,10-anthraquinone with thionyl chloride.The reaction of 9-hydroxy-10-chloro-1,4-anthraquinone and its nitro derivatives with the carbanion generated from malonic ester leads to selective alkylation at position 3.Together, the indicated reactions make it possible to realize the regioselective synthesis of 2-methyl-1,4,8- and 2-methyl-1,4,5-trihydroxy-9,10-anthraquinones.
