38735-62-5Relevant 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.
Pyrolysis of Aryl Azides. VIII. Hammett Correlations of Rates of Pyrolysis of Substituted 2-Azidobenzophenones
Dyall, Leonard K.,Karpa, Gary J.
, p. 1231 - 1241 (2007/10/02)
Eight 2-azidobenzophenones with 4- or 5-substituents have been pyrolysed in decalin solution to yield 3-phenyl-2,1-benzisoxazoles.Rate values at 100 deg are correlated with the Hammett substituent constants, with respect to both the azido (A) and benzoyl (B) reaction centres, and yield the eqation log k = -4.38 + 2.08?-A -1.52?B.There is a similar equation for rates measured at 120 deg.Although nitro and benzoyl differ considerably in their neighbouring group abilitites in azide pyrolyses, it is concluded that they exert their effects through the same mechanism.The results are consistent with both published variants of an electrocyclic mechanism (Dyall; Smith, Budde and Chou).
