REACTIONS OF 9-CHLORO-1,10-ANTHRAQUINONE 1-DICHLOROPHOSPHORYLIMINE WITH N-NUCLEOPHILES AND C-NUCLEOPHILES

9-Chloro-1,10-anthraquinone 1-dichlorophosphorylimine formed in the re action of 1-amino-9,10-anthraquinone with PCl5 followed by dehydrochlo rination reacts with primary amines with substitution of chlorine atom s. In the case of aliphatic amines, the reaction occurs further concur rently in two directions: the addition of the amine molecule with the formation of 9,9-di(alkylamino) derivatives of the anthrone and the su bstitution of hydrogen atom at position 4 with the formation of 4,9-di (alkylamino) derivatives of 1,10-anthraquinone 1-imine. In the case of aromatic amines, 1-amino-9,10-anthraquinone 9-arylimines are the end products. Reactions with the anions of CH-acids containing an alkoxyca rbonyl or cyano group occur with substitution in position 9 followed b y intramolecular cyclization with the formation of 2-alkoxy- or 2-amin o-7H-dibenzo[f,ij]isoquinolin-7-one derivatives, respectively.