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One-Pot Synthesis of 2-Acety1-1H-pyrroles from N-Propargylic beta-Enaminones via Intermediacy of 1,4-Oxazepines

Kanova, Nilay; Dundar, Buse Aysen; Kelgokmen, Yilmaz; Zora, Metin


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  <identifier identifierType="URL">https://aperta.ulakbim.gov.tr/record/231356</identifier>
  <creators>
    <creator>
      <creatorName>Kanova, Nilay</creatorName>
      <givenName>Nilay</givenName>
      <familyName>Kanova</familyName>
      <affiliation>Middle East Tech Univ, Dept Chem, TR-06800 Ankara, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Dundar, Buse Aysen</creatorName>
      <givenName>Buse Aysen</givenName>
      <familyName>Dundar</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>One-Pot Synthesis Of 2-Acety1-1H-Pyrroles From N-Propargylic Beta-Enaminones Via Intermediacy Of 1,4-Oxazepines</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/231356</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsIdenticalTo">10.1021/acs.joc.1c00077</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 one pot two step protocol for the synthesis of 2-acetyl-1H-pyrroles from N-propargylic beta-enaminones was described. When treated with zinc chloride in refluxing chloroform, N-propargylic beta-enaminones produced in situ 2-methylene-2,3-dihydro-1,4-oxazepines, which, upon further refluxing in methanol with zinc chloride, afforded 2-acetyl-1H-pyrroles. The process was found to be general for a wide variety of N-propargylic beta-enaminones and yielded a diverse range of 2-acetyl-1H-pyrroles in good to high yields with large substrate scope and good functional group tolerance. This operationally easy method may provide a rapid access to functionalized 2-acetyl-1H-pyrroles of pharmacological interest.</description>
  </descriptions>
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