New modification of the Perkow reaction: halocarboxylate anions as leaving groups in 3-acyloxyquinoline-2,4(1H,3H)-dione compounds

Substituted 3-(fluoroacyloxy)quinoline-2,4(1H,3H)-diones including 3-(fluoroiodoacetoxy) derivatives react with triethyl phosphite to afford either the product of the Perkow reaction or the corresponding 4-ethoxyquinolin-2(1H)-one. In both reactions, the fluorocarboxylate anion acts as the first obs...

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Detalles Bibliográficos
Autores principales: Paleta, Oldřich, Pomeisl, Karel, Kafka, Stanislav, Klásek, Antonín, Kubelka, Vladislav
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2005
Materias:
Preliminary Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1399465/
https://www.ncbi.nlm.nih.gov/pubmed/16551375
http://dx.doi.org/10.1186/1860-5397-1-17
Descripción
Sumario:Substituted 3-(fluoroacyloxy)quinoline-2,4(1H,3H)-diones including 3-(fluoroiodoacetoxy) derivatives react with triethyl phosphite to afford either the product of the Perkow reaction or the corresponding 4-ethoxyquinolin-2(1H)-one. In both reactions, the fluorocarboxylate anion acts as the first observed leaving group. This observation restricts the application of the intramolecular Horner-Wadsworth-Emmons synthesis to modify quinoline-2,4(1H,3H)-diones by the annulation of fluorinated but-2-enolide rings.

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