Chemistry of Heterocyclic Compounds p. 704 - 707 (1980)
Update date:2022-08-04
Topics:
Gornostaev, L. M.
Zeibert, G. F.
Zolotareva, G. I.
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.
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