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Activation and regioselectivity of five-membered cyclic thionocarbamates to nucleophilic attack

Awheda, Ismail; Saygili, Nezire; Garner, A. Christopher; Wallis, John D.


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  <identifier identifierType="URL">https://aperta.ulakbim.gov.tr/record/15111</identifier>
  <creators>
    <creator>
      <creatorName>Awheda, Ismail</creatorName>
      <givenName>Ismail</givenName>
      <familyName>Awheda</familyName>
      <affiliation>Nottingham Trent Univ, Sch Sci &amp; Technol, Nottingham NG11 8NS, England</affiliation>
    </creator>
    <creator>
      <creatorName>Saygili, Nezire</creatorName>
      <givenName>Nezire</givenName>
      <familyName>Saygili</familyName>
      <affiliation>Hacettepe Univ, Fac Pharm, Dept Basic Pharmaceut Sci, TR-06100 Ankara, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Garner, A. Christopher</creatorName>
      <givenName>A. Christopher</givenName>
      <familyName>Garner</familyName>
      <affiliation>Nottingham Trent Univ, Sch Sci &amp; Technol, Nottingham NG11 8NS, England</affiliation>
    </creator>
    <creator>
      <creatorName>Wallis, John D.</creatorName>
      <givenName>John D.</givenName>
      <familyName>Wallis</familyName>
      <affiliation>Nottingham Trent Univ, Sch Sci &amp; Technol, Nottingham NG11 8NS, England</affiliation>
    </creator>
  </creators>
  <titles>
    <title>Activation And Regioselectivity Of Five-Membered Cyclic Thionocarbamates To Nucleophilic Attack</title>
  </titles>
  <publisher>Aperta</publisher>
  <publicationYear>2013</publicationYear>
  <dates>
    <date dateType="Issued">2013-01-01</date>
  </dates>
  <resourceType resourceTypeGeneral="Text">Journal article</resourceType>
  <alternateIdentifiers>
    <alternateIdentifier alternateIdentifierType="url">https://aperta.ulakbim.gov.tr/record/15111</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsIdenticalTo">10.1039/c3ra41074a</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">The cyclic thionocarbamate of alaninol undergoes nucleophilic attack by sulfur nucleophiles at 5-C to give 1-thiopropyl-2-amine derivatives when derivatised on nitrogen with a Boc group. Iodide under microwave conditions causes a rearrangement to the isomeric thiazolidinone, while "hard" nucleophiles react at the thione group to yield a variety of product types by subsequent C-N or C-O cleavage. X-ray crystallography studies showed that the N-Boc group reduces delocalisation of electron density from nitrogen into the thione group, and thus promotes activation of the ring to nucleophilic attack.</description>
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