87999-66-4Relevant articles and documents
A divergent and selective synthesis of isomeric benzoxazoles from a single N-Cl imine
Chen, Cheng-Yi,Andreani, Teresa,Li, Hongmei
, 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.
2-Benzazepines. 8. Zerovalent nickel mediated biaryl synthesis of an anxiolytic pyrimido[5,4-d][2]benzazepine
Coffen,Schaer,Bizzarro,Cheung
, p. 296 - 300 (2007/10/02)
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