Abstract
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 of 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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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 912–915, July, 1980.
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Gornbstaev, L.M., Zeibert, G.F. & Zolotareva, G.I. Amination of anthra [ 1, 9-c, d ] isoxazol-6-ones. Chem Heterocycl Compd 16, 704–707 (1980). https://doi.org/10.1007/BF00557740
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DOI: https://doi.org/10.1007/BF00557740