Limitations of the Wittig–Horner-type annulation of fluorobutenolide moiety to 3-hydroxyquinoline-2,4(2H,3H)-diones. Novel modifications of the Perkow reaction including fluorinated acyloxy leaving groups

Autor:	Karel Pomeisl, Antonín Klásek, Oldřich Paleta, Vladislav Kubelka, Jan Čejka, Jaroslav Kvíčala, Jaroslav Havlíček, Stanislav Kafka
Rok vydání:	2007
Předmět:	Annulation Organic Chemistry Leaving group Perkow reaction Biochemistry Medicinal chemistry chemistry.chemical_compound chemistry Intramolecular force Drug Discovery Wittig reaction Organic chemistry Moiety Derivative (chemistry)
Zdroj:	Tetrahedron. 63:10549-10561
ISSN:	0040-4020
Popis:	3-(Fluoroacyloxy)quinoline-2,4(1H,3H)-diones 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 leaving group. For the corresponding 3-(fluoroiodoacetoxy) derivative this observation precludes the application of the intramolecular Wittig–Horner synthesis to modify quinoline-2,4(1H,3H)-diones by the annulation of a fluorinated but-2-enolide moiety.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::44382e4afc70e04fe2bea60ba989cc44 https://doi.org/10.1016/j.tet.2007.07.058 Zobrazit plný text záznamu Full Text from ScienceDirect