Author/Authors :
Coldham، نويسنده , , Iain and Adams، نويسنده , , Harry and Ashweek، نويسنده , , Neil J. and Barker، نويسنده , , Thomas A. and Reeder، نويسنده , , Andrew T. and Skilbeck، نويسنده , , Melanie C.، نويسنده ,
Abstract :
Lithiation with butyllithium of 2-(benzylamino)benzamides (N-benzyl anthranilamides) occurs at the benzylic position to give an α-amino-organolithium that cyclizes to the 3-indolinone (indoxyl) ring (similar to a Parham cyclization). Autoxidation in air gives 2-hydroxy-3-indolinones. In the absence of a proton source, rearrangement of the aryl group from C-2 to C-3 occurs to give the 3-hydroxy-2-indolinone (oxindole) ring.
