No abstract

9-Chloro-l,10-anthraquinone l-dichlorophosphorylimine formed in the reaction of I-amino-9,10-anthraquinone with PCI 5 followed by dehydrochlorination reacts with primary amines with substitution of chlorine atoms. In the case of aliphatie amines, the reaction occurs further concurrently in two directions: the addition of the amine molecule with the formation of 9,9-di(alkylamino) derivatives of the anthrone and the substitution of hydrogen atom at position 4 with the formation of 4,9-di(alkylamino) derivatives of 1,10-anthraquinone 1 Amine. In the case of aromatic amines, l-amino-9,10-anthraquinone 9-arylimines are the end products. Reactions with the anions of CH-acids containing an alkoxycarbonyl or cyano group occur with substitution in position 9 followed by intramolecular cyclization with the formation of 2-alkoxy-or 2-amino-7H-dibenzo[f,/j]isoquinolin-7-one derivatives, respectively.

l-Dichlorophosphoryloxy-9,9-dichloroanthrone, a product of the reaction between I-hydroxyanthraquinone and PCI 5, reacts with primary amines in benzene to give first l-(diaminophosphoryloxy)-9,9-dichloroanthrones and then the corresponding 9-imines. The reaction in DMF occurs with elimination of the phosphoryloxy group and generation of 9-chloro-l,10-anthraquinone that undergoes amination followed by substitution of the hydrogen atom in position 4 rather than a chlorine atom in position 9, which is the most active position in 2,4,9-trichtoro-1,10-anthraquinone. The second step of amination results in 4,9-di(alkylamino)-l,10-anthraquinone. The literature data on obtaining individual 9-chloro-l,10-anthraquinone under the action of bases on l-dichorophosphoryloxy-9,9-dichloroanthrone were not experimentally supported.