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Synthesis of 1-Azaspiro[4.5]deca-1,3-dienes from N-Propargylic beta-Enaminones in Basic Medium

Karadeniz, Eda; Zora, Metin


DataCite XML

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  <identifier identifierType="URL">https://aperta.ulakbim.gov.tr/record/70543</identifier>
  <creators>
    <creator>
      <creatorName>Karadeniz, Eda</creatorName>
      <givenName>Eda</givenName>
      <familyName>Karadeniz</familyName>
      <affiliation>Middle East Tech Univ, Dept Chem, TR-06800 Ankara, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Zora, Metin</creatorName>
      <givenName>Metin</givenName>
      <familyName>Zora</familyName>
      <affiliation>Middle East Tech Univ, Dept Chem, TR-06800 Ankara, Turkey</affiliation>
    </creator>
  </creators>
  <titles>
    <title>Synthesis Of 1-Azaspiro[4.5]Deca-1,3-Dienes From N-Propargylic Beta-Enaminones In Basic Medium</title>
  </titles>
  <publisher>Aperta</publisher>
  <publicationYear>2019</publicationYear>
  <dates>
    <date dateType="Issued">2019-01-01</date>
  </dates>
  <resourceType resourceTypeGeneral="Text">Journal article</resourceType>
  <alternateIdentifiers>
    <alternateIdentifier alternateIdentifierType="url">https://aperta.ulakbim.gov.tr/record/70543</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsIdenticalTo">10.1055/s-0037-1611723</relatedIdentifier>
  </relatedIdentifiers>
  <rightsList>
    <rights rightsURI="http://www.opendefinition.org/licenses/cc-by">Creative Commons Attribution</rights>
    <rights rightsURI="info:eu-repo/semantics/openAccess">Open Access</rights>
  </rightsList>
  <descriptions>
    <description descriptionType="Abstract">A facile, efficient and unprecedented method for the synthesis of spiro-2H-pyrroles is reported. When reacted with 1-ethynylcyclohexylamine, a, ss-alkynic ketones produced cyclohexane-embedded Npropargylic ss-enaminones, which in the presence of cesium carbonate underwent nucleophilic cyclization to afford 1-azaspiro[ 4.5] deca-1,3diene derivatives in good to excellent yields. This cyclization was found to be general for a variety of cyclohexane-embedded N-propargylic ss enaminones and demonstrated good tolerance to a broad range of aliphatic, aromatic and heteroaromatic groups with electron-withdrawing and electron-donating substituents. The decoration of pyrrole compounds with a spiro framework may exhibit potential for the synthesis of molecules of pharmacological interest.</description>
  </descriptions>
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