90408-03-0Relevant academic research and scientific papers
Synthesis of 2-substituted 4H-3,1-benzoxazin-4-ones by thermally induced cyclization of N-(2-benzyloxycarbonyl)phenyl ketenimines; oxygen-to-carbon migration of a benzyl group
Alajarin, Mateo,Vidal, Angel,Ortin, Maria-Mar,Bautista, Delia
, p. 2426 - 2432 (2007/10/03)
N-(2-Benzyloxycarbonyl)phenyl ketenimines undergo a thermally induced cyclization to give 2-substituted 4H-3,1-benzoxazin-4-ones. These processes involve the formation of a new carbon-oxygen bond and the migration of the benzyl group from the oxygen atom of the benzyloxy unit at the ester function to the terminal carbon atom of the ketenimine fragment. Georg Thieme Verlag Stuttgart.
The Pyrolysis of 2-Azidobenzoates. A New Synthesis of Carbazoles and Other N-Heterocycles
Clancy, Michael G.,Hesabi, Massoud M.,Meth-Cohn, Otto
, p. 429 - 434 (2007/10/02)
The spray pyrolysis of aryl 2-azidobenzoates yields carbazoles, involving a rearrangement whereby the nitrogen of the product is attached to the aryl 1-carbon, a process involving a spiro 6-membered intermediate.When the aryl ortho-positions were both alkyl substituted the product was ab acridan instead.With an ortho-carboxylate, acridone formation competed with that of carbazole.When the CO-O group of the substrate was replaced by O-CO, CO-S, CO-NPh, or SO2-O the pyrolysis was ineffective.Benzyl 2-azidobenzoates, however, pyrolysed to yield 1-benzyl-2,1-benzisoxazolones by an unprecedented C-O insertion reaction of the intermediate nitrene.
