Helvetica Chimica Acta p. 411 - 421 (1983)
Update date:2022-08-03
Topics:
Adam, Jean-Marie
Winkler, Tammo
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-(benz
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