From Ketenimines to Ketenes to Quinolones:  Two Consecutive Pseudopericyclic Events

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...

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Bibliographic Details
Published in:Organic letters 2005-11, Vol.7 (23), p.5281-5284
Main Authors: Alajarín, Mateo, Ortín, María-Mar, Sánchez-Andrada, Pilar, Vidal, Ángel, Bautista, Delia
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol052189v