83206-52-4Relevant academic research and scientific papers
NUCLEOPHILIC SUBSTITUTION OF HYDROGEN IN AROMATIC SYSTEMS. II. MECHANISM OF AMINATION IN ANTHRAISOXAZOL-6-ONES
Galushko, A. M.,Dokunikhin, N. S.
, p. 1347 - 1357 (2007/10/02)
The nucleophilic substitution of the C5-H hydrogen atom in anthraisoxazol-6-ones by amines in acetonitrile in the absence of Cu2+, Ag+, Co2+, or Ni2+ cations takes place with the formation of strong hydrogen bond in the sixmembered chelate ring of the product from 1,4-addition of the amine to the isoxazolone at the C5 and =O atoms.The structure of the reaction product is determined by the character of the amine, and (with the absence of readily eliminated groups) substitution of C5-H is suppressed by the competing amination of C3-H and reduction of the heterocycle.The substitution of C5-Hlg by amines under analogous conditions leads to trivial reaction products.In nitromethane C3-H or C3-Hlg is mainly substituted, and C5-H or C5-Hlg is partly substituted, leading to products with trivial structures.In the presence of Cu2+, Ag+, Co2+, Ni2+ cations in acetonitrile only C3-H or C3-Hlg is substituted through the formation of mixed complex of amine and isoxazolone on the cation.
