870647-74-8Relevant articles and documents
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.