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Synthesis of 3-Amino-4-iodothiophenes through Iodocyclization of 1-(1,3-Dithian-2-yl)propargylamines

Ismailoglu, Eda; Mert, Zeynep; Dinc, Mert; Kaya, Kerem; Yucel, Baris


DataCite XML

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  <identifier identifierType="URL">https://aperta.ulakbim.gov.tr/record/234850</identifier>
  <creators>
    <creator>
      <creatorName>Ismailoglu, Eda</creatorName>
      <givenName>Eda</givenName>
      <familyName>Ismailoglu</familyName>
      <affiliation>Istanbul Tech Univ, Fac Sci, Dept Chem, TR-34469 Istanbul, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Mert, Zeynep</creatorName>
      <givenName>Zeynep</givenName>
      <familyName>Mert</familyName>
      <affiliation>Istanbul Tech Univ, Fac Sci, Dept Chem, TR-34469 Istanbul, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Dinc, Mert</creatorName>
      <givenName>Mert</givenName>
      <familyName>Dinc</familyName>
      <affiliation>Istanbul Tech Univ, Fac Sci, Dept Chem, TR-34469 Istanbul, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Kaya, Kerem</creatorName>
      <givenName>Kerem</givenName>
      <familyName>Kaya</familyName>
      <affiliation>Istanbul Tech Univ, Fac Sci, Dept Chem, TR-34469 Istanbul, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Yucel, Baris</creatorName>
      <givenName>Baris</givenName>
      <familyName>Yucel</familyName>
      <affiliation>Istanbul Tech Univ, Fac Sci, Dept Chem, TR-34469 Istanbul, Turkey</affiliation>
    </creator>
  </creators>
  <titles>
    <title>Synthesis Of 3-Amino-4-Iodothiophenes Through Iodocyclization Of 1-(1,3-Dithian-2-Yl)Propargylamines</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/234850</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsIdenticalTo">10.1002/ejoc.202100483</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">1-(1,3-Dithian-2-yl)propargylamines undergo iodo-cylization regioselectively to afford tetrasubstituted 3-amino-4-iodothiophenes in 30-87 % yields by iodide induced cleavage of dithiane ring in a bicyclic sulfonium intermediate. A mechanism for this unprecedented transformation was proposed and tentatively supported by the isolation of an intermediate structure. 1-(1,3-Dithian-2-yl)propargylamines were prepared in 30-94 % yields by Au-catalyzed one-pot, three-component reaction of 1,3-dithiane-2-carbaldehydes, amines, and alkynes so called A(3)-coupling reaction.</description>
  </descriptions>
</resource>
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