35. Ueber die Dicyanierung der 1,4-Diaminoanthrachinone und die Reactivitaet der 1,4-Diamino-9,10-dioxo-9,10-dihydroanthracen-2,3-dicarbonitrile gegenueber nucleophilen Reagenzien

Article abstract of DOI:10.1002/hlca.19830660203

The reaction of 1-amino-9,10-dioxo-4-phenylamino-9,10-dihydroanthracene-2-sulfonic acid (1, R=C6H5) with cyanide in water yields a mixture of 1-amino-9,10-dioxo-4-phenylamino-9,10-dihydroanthracene-2-carbonitrile (3, R=C6H5) and 1-amino-4-(phenylamino)anthraquinone (4, R=C6H5) under the usual reaction conditions (Scheme 1).In dimethylsulfoxide, however, a second cyano group is introduced, and 1-amino-9,10-dioxo-4-phenylamino-9,10-dihydroanthracene-2,3-dicarbonitrile (7) is formed (Scheme 2).The cyano groups are very reactive towards nucleophiles.The cyano group in 2-position can be substituted by hydroxide and aliphatic amines (Schemes 5 and 6).The cyano group in 3-position can be eliminated by aliphatic amines and hydrazine (Scheme 7).Nucleophilic attack at the cyano C-atom of the 2-cyano group by suitable reagents leads to ring formation, yielding e.g. 2-(Δ²-1,3-oxazolin-2-yl)-, 2-(benzimidazol-2-yl)- and 2-(1H-tetrazol-5-yl)anthraquinones (Schemes 8 and 10).