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SYNTHESIS AND REACTIONS OF FURANANTHRONES
Gorelik, M.V.,Alimova, R.A.
, p. 745 - 751 (2007/10/02)
1-(Methoxycarbonyl)chloromethylanthraquines, obtained from diazotized 1-aminoanthraquinones and trichloroethylene by the Meerwein reaction, undergo cyclization to 2-methoxycarbonyl-6H-anthrafuran-6-ones when heated.The action of oxidizing agents on the latter leads to the formation of 1-methoxalylanthraquinones, which can be converted back into 2-methoxycarbonylanthrafuranones by reduction with aluminum in sulfuric acid.The action of amines leads to nucleophilic substitution of the chlorine atom or hydrogen atom at position 5 of the anthrafuranone to form the corresponding 5-amino derivatives.Entering into a Diels-Alder reaction, 2-methoxycarbonylanthrafuranones add dienophiles of the RCH=CH2 type regiospecifically and are converted after aromatization of the adducts into 1-R-substituted derivatives of the benzanthrone series.
