37892-44-7Relevant articles and documents
Gold-catalyzed cyclization of 1-(2′-Azidoaryl) propynols: Synthesis of polysubstituted 4-quinolones
Wu, Xiang,Zheng, Lang-Lang,Zhao, Li-Ping,Zhu, Cheng-Feng,Li, You-Gui
, p. 14769 - 14772 (2019/12/24)
An unprecedented gold-catalyzed procedure for the synthesis of polysubstituted 4-quinolones from 1-(2′-Azidoaryl) propynols is described. The reaction undergoes an intramolecular nucleophilic attack of the azide group to the Au-Activated triple bonds in a 6-endo-dig manner and subsequent gold-Assisted expulsion of N2 to furnish an α-imino gold carbene intermediate, which triggers a 1,2-carbon migration and finally is converted to 2,3-disubstituted 4-quinolone.
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.