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
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F70883521%3A28110%2F07%3A63505282" target="_blank" >RIV/70883521:28110/07:63505282 - isvavai.cz</a>
Alternative codes found
RIV/61388963:_____/07:00085693 RIV/60461373:22310/07:00018525
Result on the web
—
DOI - Digital Object Identifier
—
Alternative languages
Result language
angličtina
Original language name
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
Original language description
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. Forthe 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.
Czech name
Omezení Wittigovy-Hornerovy cyklizace fluorbutenolidové skupiny na 3-hydroxychinoline-2,4(2H,3H)-diony. Nové modifikace Perkowovy reakce s odstupující fluorovanou acyloxylovou skupinou.
Czech description
3-(Fluoracyloxy)chinolin-2,4(1H,3H)-diony reagují s triethyl-fosfitem buď za vzniku produktu Perkowovy reakce nebo za vzniku odpovídajícího 4-ethoxychinolin-2(1H)-onu. V obou reakcích je odstupující skupinou fluorkarboxylátový anion. U odpovídajícího 3-(fluorjodacetoxy)derivátu toto pozorování vylučuje využití intramolekulární Wittigovy-Hornerovy syntézys k modifikaci chinolin-2,4(1H, 3H)-dionů cyklizací fluorované but-2-enolidové skupiny.
Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
—
Result continuities
Project
<a href="/en/project/GA203%2F07%2F0320" target="_blank" >GA203/07/0320: Transformations of 3-hydroxy, 3-amino, and 3-thiocyanatoquinoline-2,4(1H,3H)-diones to novel heterocyclic systems</a><br>
Continuities
Z - Vyzkumny zamer (s odkazem do CEZ)
Others
Publication year
2007
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Tetrahedron
ISSN
0040-4020
e-ISSN
—
Volume of the periodical
—
Issue of the periodical within the volume
63
Country of publishing house
GB - UNITED KINGDOM
Number of pages
13
Pages from-to
10549-10561
UT code for WoS article
—
EID of the result in the Scopus database
—