- Ring Opening Reactions of 6H-Anthraisoxazol-6-ones and Related Compounds
-
Nucleophilic attack of anthraisoxazol-6-ones, and of anthraisoxazole by various sulfoxides, triphenyl phosphine, and aliphatic or aromatic phosphites proceeded with cleavage of the nitrogen-oxygen bond of the isoxazole ring.This method provided ready access to substituted anthraquinones bearing sulfoximido-, triphenylphosphazo-, and dialkyl(aryl)phosphoramidic groups attached to the 1- and the 1,5-positions of the anthraquinone system.The structures of the newly synthesized anthraquinone derivatives were supported by analytical and spectral data. 1 -S,S-dimethyl-N-(5-benzamidoanthraquinon-1-yl)sulfoximide yielded in 90percent sulfuric acid the 1-amino-5-sulfoximido anthraquinone without hydrolyzing the sulfoximido group.
- Sutter, P.,Weis, C. D.
-
p. 997 - 1011
(2007/10/02)
-
- AMINATION OF ANTHRAISOXAZOL-6-ONES
-
The behavior of 3,5-dihalo derivatives of anthraisoxazol-6-one with respect to primary and secondary amines was studied. 5-Chloroanthraisoxazol-6-one undergoes amination particularly readily.The products of the reaction of isoxazoles with amines are the corresponding amino derivatives.The amination of 5-chloroanthraisoxazol-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-chloroanthraisoxazol-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.
- Gornostaev, L. M.,Zeibert, G. F.,Zolotareva, G. I.
-
p. 704 - 707
(2007/10/02)
-