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A new approach for the synthesis of spiro and gem-dimethyl-substituted 1,4-oxazepines from N-propargylic beta-enaminones

Karadeniz, Eda; Kelgokmen, Yilmaz; Zora, Metin


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  <identifier identifierType="URL">https://aperta.ulakbim.gov.tr/record/4525</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>Kelgokmen, Yilmaz</creatorName>
      <givenName>Yilmaz</givenName>
      <familyName>Kelgokmen</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>A New Approach For The Synthesis Of Spiro And Gem-Dimethyl-Substituted 1,4-Oxazepines From N-Propargylic Beta-Enaminones</title>
  </titles>
  <publisher>Aperta</publisher>
  <publicationYear>2021</publicationYear>
  <dates>
    <date dateType="Issued">2021-01-01</date>
  </dates>
  <resourceType resourceTypeGeneral="Text">Journal article</resourceType>
  <alternateIdentifiers>
    <alternateIdentifier alternateIdentifierType="url">https://aperta.ulakbim.gov.tr/record/4525</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsIdenticalTo">10.1002/jhet.4183</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">An efficient and general method for the synthesis of spiro-1,4-oxazepines and 3,3-dimethyl-1,4-oxazepines is reported. When treated with ZnI2 and AgSbF6 in refluxing DCE, cyclohexane-embedded N-propargylic beta-enaminones underwent 7-exo-dig cyclization to afford spiro-1,4-oxazepines, specifically 12-methylene-11-oxa-7-azaspiro[5.6]dodeca-7,9-dienes, in good to high yields. Accordingly, N-(1,1-dimethyl)propargylic beta-enaminones produced 3,3-dimethyl-1,4-oxazepines. Cyclization was found to be general for a diverse range of N-propargylic beta-enaminones with high efficiency and broad functional group tolerance. This operationally easy method might provide quick access to a library of functionalized spiro and gem-dimethyl-substituted 1,4-oxazepine derivatives of pharmacological interest.</description>
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