845266-67-3Relevant academic research and scientific papers
Intramolecular hydrogen-bond activation for the addition of nucleophilic imines: 2-hydroxybenzophenone as a chemical auxiliary
Choubane, Houcine,Garrido-Castro, Alberto F.,Alvarado, Cuauhtemoc,Martín-Somer, Ana,Guerrero-Corella, Andrea,Daaou, Mortada,Díaz-Tendero, Sergio,Carmen Maestro,Fraile, Alberto,Alemán, José
supporting information, p. 3399 - 3402 (2018/04/05)
The addition of nucleophilic imines, using 2-hydroxybenzophenone as a chemical auxiliary, is presented. An intramolecular six-membered ring via hydrogen bonding that enhances the reactivity and selectivity is the key of this strategy, which is supported b
A divergent and selective synthesis of isomeric benzoxazoles from a single N-Cl imine
Chen, Cheng-Yi,Andreani, Teresa,Li, Hongmei
supporting information; experimental part, p. 6300 - 6303 (2012/01/05)
A divergent and regioselective synthesis of either 3-substituted benzisoxazoles or 2-substituted benzoxazoles from readily accessible ortho-hydroxyaryl N-H ketimines is described. The reaction proceeds in two distinct pathways through a common N-Cl imine intermediate: (a) N-O bond formation to form benzisoxazole under anhydrous conditions and (b) NaOCl mediated Beckmann-type rearrangement to form benzoxazole, respectively. The reaction path also depends on the electronic nature of the aromatic ring, with the electron-rich aromatic rings favoring the rearrangement and the electron-deficient rings favoring the N-O bond formation. A Beckmann-type rearrangement mechanism via net [1,2]-aryl migration for the formation of 2-substituted benzoxazole is proposed.
