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From ketenimines to ketenes to quinolones: two consecutive pseudopericyclic events

, : From ketenimines to ketenes to quinolones: two consecutive pseudopericyclic events. Organic Letters 7(23): 5281-5284

[reaction: see text] 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 6pi-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.


PMID: 16268558

DOI: 10.1021/ol052189v

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