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Keteniminium Salts as Key Intermediates for the Efficient Synthesis of 3-Amino-Indoles and -Benzofurans

Dagoneau, Dylan; Kolleth, Amandine; Quinodoz, Pierre; Tanriver, Gamze; Catak, Saron; Lumbroso, Alexandre; Sulzer-Mosse, Sarah; De Mesmaeker, Alain


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  <identifier identifierType="URL">https://aperta.ulakbim.gov.tr/record/5969</identifier>
  <creators>
    <creator>
      <creatorName>Dagoneau, Dylan</creatorName>
      <givenName>Dylan</givenName>
      <familyName>Dagoneau</familyName>
      <affiliation>Syngenta Crop Protect AG, Crop Protect Res, Res Chem, CH-4332 Stein, Switzerland</affiliation>
    </creator>
    <creator>
      <creatorName>Kolleth, Amandine</creatorName>
      <givenName>Amandine</givenName>
      <familyName>Kolleth</familyName>
      <affiliation>Syngenta Crop Protect AG, Crop Protect Res, Res Chem, CH-4332 Stein, Switzerland</affiliation>
    </creator>
    <creator>
      <creatorName>Quinodoz, Pierre</creatorName>
      <givenName>Pierre</givenName>
      <familyName>Quinodoz</familyName>
      <affiliation>Syngenta Crop Protect AG, Crop Protect Res, Res Chem, CH-4332 Stein, Switzerland</affiliation>
    </creator>
    <creator>
      <creatorName>Tanriver, Gamze</creatorName>
      <givenName>Gamze</givenName>
      <familyName>Tanriver</familyName>
      <affiliation>Bogazici Univ, Dept Chem, TR-34342 Istanbul, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Catak, Saron</creatorName>
      <givenName>Saron</givenName>
      <familyName>Catak</familyName>
      <affiliation>Bogazici Univ, Dept Chem, TR-34342 Istanbul, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Lumbroso, Alexandre</creatorName>
      <givenName>Alexandre</givenName>
      <familyName>Lumbroso</familyName>
      <affiliation>Syngenta Crop Protect AG, Crop Protect Res, Res Chem, CH-4332 Stein, Switzerland</affiliation>
    </creator>
    <creator>
      <creatorName>Sulzer-Mosse, Sarah</creatorName>
      <givenName>Sarah</givenName>
      <familyName>Sulzer-Mosse</familyName>
      <affiliation>Syngenta Crop Protect AG, Crop Protect Res, Res Chem, CH-4332 Stein, Switzerland</affiliation>
    </creator>
    <creator>
      <creatorName>De Mesmaeker, Alain</creatorName>
      <givenName>Alain</givenName>
      <familyName>De Mesmaeker</familyName>
      <affiliation>Syngenta Crop Protect AG, Crop Protect Res, Res Chem, CH-4332 Stein, Switzerland</affiliation>
    </creator>
  </creators>
  <titles>
    <title>Keteniminium Salts As Key Intermediates For The Efficient Synthesis Of 3-Amino-Indoles And -Benzofurans</title>
  </titles>
  <publisher>Aperta</publisher>
  <publicationYear>2020</publicationYear>
  <dates>
    <date dateType="Issued">2020-01-01</date>
  </dates>
  <resourceType resourceTypeGeneral="Text">Journal article</resourceType>
  <alternateIdentifiers>
    <alternateIdentifier alternateIdentifierType="url">https://aperta.ulakbim.gov.tr/record/5969</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsIdenticalTo">10.1002/hlca.201900217</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">Herein, we describe a high yielding approach towards the synthesis of 3-amino-indoles and -benzofurans through 6 pi-electrocyclization. This was made possible by taking advantage of the high reactivity of keteniminium salts, formed in-situ by treating with triflic anhydride and 2-fluoropyridine amides bearing at the alpha-position either an aniline or a phenoxy moiety. These mild conditions, on top of furnishing rapidly the 3-aminobenzoheteroles, allow the tolerance of various functional groups. Control experiments were carried out to highlight that the keteniminium is, indeed, in most cases, the reactive intermediate and conformational preferences of such species were investigated through a DFT study.</description>
  </descriptions>
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