From ketenimines to ketenes to quinolones:: Two consecutive pseudopericyclic events

被引：38

作者：

Alajarín, M

Ortín, MM

Sánchez-Andrada, P

Vidal, A

Bautista, D

机构：

[1] Univ Murcia, Dept Quim Organ, Fac Quim, E-30100 Murcia, Spain

[2] Univ Murcia, Serv Univ Instrumentac Cientif, E-30100 Murcia, Spain

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 23期

关键词：

D O I：

10.1021/ol052189v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 6 pi-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.

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页码：5281 / 5284

页数：4

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