Omezení Wittigovy-Hornerovy cyklizace fluorbutenolidové skupiny na 3-hydroxychinoline-2,4(2H,3H)-diony. Nové modifikace Perkowovy reakce s odstupující fluorovanou acyloxylovou skupinou.

Pomeisl, K.; Kvíčala, J.; Paleta, O.; Klásek, Antonín; Kafka, Stanislav; Kubelka, V.; Havlíček, J.; Čejka, J.

Title:

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

Author:

Pomeisl, K.; Kvíčala, J.; Paleta, O.; Klásek, Antonín; Kafka, Stanislav; Kubelka, V.; Havlíček, J.; Čejka, J.

Document type:

Peer-reviewed article (English)

Source document:

Tetrahedron. 2007, vol. 63, issue 42, p. 10549-10561

ISSN:

0040-4020 (Sherpa/RoMEO, JCR)

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DOI:

https://doi.org/10.1016/j.tet.2007.07.058

Abstract:

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.

Full text:

https://www.sciencedirect.com/science/article/pii/S0040402007012896

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Citace článku v časopise:
POMEISL, K., J. KVÍČALA, O. PALETA, Antonín KLÁSEK, Stanislav KAFKA, V. KUBELKA, J. HAVLÍČEK a J. ČEJKA. Omezení Wittigovy-Hornerovy cyklizace fluorbutenolidové skupiny na 3-hydroxychinoline-2,4(2H,3H)-diony. Nové modifikace Perkowovy reakce s odstupující fluorovanou acyloxylovou skupinou. Tetrahedron [online]. 2007, vol. 63, iss. 42, s. 10549-10561. [cit. 2024-04-24]. ISSN 0040-4020. Dostupné z: https://www.sciencedirect.com/science/article/pii/S0040402007012896.

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