AMINATION OF ANTHRAISOXAZOL-6-ONES

Article abstract of DOI:10.1007/BF00557740

The behavior of 3,5-dihalo derivatives of anthra<1,9-c,d>isoxazol-6-one with respect to primary and secondary amines was studied. 5-Chloroanthra<1,9-c,d>isoxazol-6-one undergoes amination particularly readily.The products of the reaction of isoxazoles with amines are the corresponding amino derivatives.The amination of 5-chloroanthra<1,9-c,d>isoxazol-6-one in refluxing dimethylformamide (DMF) is accompanied by reductive cleavage of the isoxazole ring and the formation of 1-amino-4-arylaminoanthraquinones.Amination in the 5 position with substitution of a hydride ion takes place primarily in the reaction of 3-chloroanthra<1,9-c,d>isoxazol-6-one with benzylamine or cyclohexylamine, whereas the chlorine in the 3 position is replaced by the action of morpholine or piperidine on the same substrate.