87828-93-1Relevant academic research and scientific papers
An In-depth Study of the Azidobenzophenone-Anthranil-Acridone Transformation
Hawkins, David G.,Meth-Cohn, Otto
, p. 2077 - 2087 (2007/10/02)
The title transformation, particularly the conversion of anthranils into acridones, is shown to be critically sensitive to temperature, solvent, substituent, and metal catalysts.Thus the conversion of 3-(p-tolyl)anthranil into an acridone gives a ratio of 2-and 3-methyl derivatives varying from 0.6:1 to 4.7:1 with changing temperature and solvent.In other similar thermolyses, solvents (e.g. 1,2,4-trichlorobenzene) were incorporated into the product and traces of metals and their derivatives had a dramatic effect on the rate and course of the reaction.The most effective catalysts were iron powder and aluminium acetylacetonate. 3-(2,6-Disubstituted phenyl)anthranils gave acridones in which the substituents were either lost or rearranged onto N or C, the last cases involving sequential -sigmatropic shifts. 3-Thienylanthranils gave related thienoquinolones on thermolysis; again the reaction were very sensitive to catalysis.Blocked thienylanthranils also gave rearrangement products, but the non-aromatic intermediates could be isolated.
