In this HOT paper Angel Vidal and co-workers at Universidad de Murcia discuss the conversion of N-(2-Substituted)aryl ketenimines into 3,4- dihydroquinolines. The reaction involves a 1,5-migration of a hydride or alkoxyl group, followed by a subsequent 6pi-electrocyclic ring closure.
Vidal et al. perform a detailed experimental study on the relative migratory aptitudes and activating effects of the 1,5- (H, RO, RS) shift / 6p-electrocyclic ring closure, and provide new interesting insights into the formation of highly substituted quinolones.
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1,5-(H, RO, RS) shift/6π-electrocyclic ring closure tandem processes on N-[(α-heterosubstituted)-2-tolyl]ketenimines: a case study of relative migratory aptitudes and activating effects
Mateo Alajarín, Baltasar Bonillo, Raúl-Angel Orenes, María-Mar Ortín and Angel Vidal
DOI: 10.1039/C2OB27010B