1140-36-9Relevant articles and documents
Metal-Free Synthesis of Anthranils by PhIO Mediated Heterocyclization of ortho-Carbonyl Anilines
Garia, Alankrita,Grover, Jatin,Jain, Nidhi
, p. 4125 - 4131 (2021/08/24)
Here, we report a metal-free synthesis of anthranils from ortho-carbonyl anilines using PhIO as a sole additive under ambient conditions. This methodology did not require any external additives and delivered anthranils in excellent yields with broad substrate scope. The mechanistic studies suggest that the reaction proceeds via in-situ generation of iminoiodane leading to nitrene and a subsequent nucleophilic attack from oxygen of ortho-carbonyl aniline on nitrene results in heterocyclization.
Intramolecular Fe(II)-Catalyzed N-O or N-N bond formation from aryl azides
Stokes, Benjamin J.,Vogel, Carl V.,Urnezis, Linda K.,Pan, Minjie,Driver, Tom G.
supporting information; experimental part, p. 2884 - 2887 (2010/08/21)
(Figure presented) Iron(II) bromide catalyzes the transformation of aryl and vinyl azides with ketone or methyl oxime substituents into 2,1-benzisoxazoles, indazoles, or pyrazoles through the formation of an N-O or N-N bond. This transformation tolerates a variety of different functional groups to facilitate access to a range of benzisoxazoles or indazoles. The unreactivity of the Z-methyloxime indicates that N-heterocycle formation occurs through a nucleophilic attack of the ketone or oxime onto an activated planar iron azide complex.
