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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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
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author Paleta, Oldřich
Pomeisl, Karel
Kafka, Stanislav
Klásek, Antonín
Kubelka, Vladislav
author_facet Paleta, Oldřich
Pomeisl, Karel
Kafka, Stanislav
Klásek, Antonín
Kubelka, Vladislav
author_sort Paleta, Oldřich
collection PubMed
description 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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spelling pubmed-13994652006-03-13 New modification of the Perkow reaction: halocarboxylate anions as leaving groups in 3-acyloxyquinoline-2,4(1H,3H)-dione compounds Paleta, Oldřich Pomeisl, Karel Kafka, Stanislav Klásek, Antonín Kubelka, Vladislav Beilstein J Org Chem Preliminary Communication 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. Beilstein-Institut 2005-12-09 /pmc/articles/PMC1399465/ /pubmed/16551375 http://dx.doi.org/10.1186/1860-5397-1-17 Text en Copyright © 2005, Paleta et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Preliminary Communication
Paleta, Oldřich
Pomeisl, Karel
Kafka, Stanislav
Klásek, Antonín
Kubelka, Vladislav
New modification of the Perkow reaction: halocarboxylate anions as leaving groups in 3-acyloxyquinoline-2,4(1H,3H)-dione compounds
title New modification of the Perkow reaction: halocarboxylate anions as leaving groups in 3-acyloxyquinoline-2,4(1H,3H)-dione compounds
title_full New modification of the Perkow reaction: halocarboxylate anions as leaving groups in 3-acyloxyquinoline-2,4(1H,3H)-dione compounds
title_fullStr New modification of the Perkow reaction: halocarboxylate anions as leaving groups in 3-acyloxyquinoline-2,4(1H,3H)-dione compounds
title_full_unstemmed New modification of the Perkow reaction: halocarboxylate anions as leaving groups in 3-acyloxyquinoline-2,4(1H,3H)-dione compounds
title_short New modification of the Perkow reaction: halocarboxylate anions as leaving groups in 3-acyloxyquinoline-2,4(1H,3H)-dione compounds
title_sort new modification of the perkow reaction: halocarboxylate anions as leaving groups in 3-acyloxyquinoline-2,4(1h,3h)-dione compounds
topic Preliminary Communication
url 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
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