90408-18-7Relevant academic research and scientific papers
From ketenimines to ketenes to quinolones: Two consecutive pseudopericyclic events
Alajarin, Mateo,Ortin, Maria-Mar,Sanchez-Andrada, Pilar,Vidal, Angel,Bautista, Delia
, p. 5281 - 5284 (2007/10/03)
(Chemical Equation Presented) N-[2-(Alkyl- or arylthio)carbonyl]phenyl ketenimines undergo cyclization under mild thermal conditions to afford 2-alkyl(aryl)thio-3H-quinolin-4-ones by means of the 1,5-migration of the alkyl(aryl)thio group from the carbonyl carbon to the central carbon atom of the ketenimine fragment followed by the 6π-electrocyclization of the resulting vinyliminoketene. These 1,5-migration and electrocyclization processes occur via transition states whose pseudopericyclic characteristics have been established on the basis of their magnetic properties, geometries, and NBO analyses.
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.
