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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