1 Ocak 2008 Dergi makalesi Açık Erişim

Sahin, Ayse; Cakmak, Osman; Demirtas, Ibrahim; Okten, Salih; Tutar, Ahmet

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  <identifier identifierType="URL">https://aperta.ulakbim.gov.tr/record/43451</identifier>
  <creators>
    <creator>
      <creatorName>Sahin, Ayse</creatorName>
      <givenName>Ayse</givenName>
      <familyName>Sahin</familyName>
      <affiliation>Gaziosmanpasa Univ, Fac Art &amp; Sci, Dept Chem, TR-60240 Tokat, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Cakmak, Osman</creatorName>
      <givenName>Osman</givenName>
      <familyName>Cakmak</familyName>
      <affiliation>Gaziosmanpasa Univ, Fac Art &amp; Sci, Dept Chem, TR-60240 Tokat, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Demirtas, Ibrahim</creatorName>
      <givenName>Ibrahim</givenName>
      <familyName>Demirtas</familyName>
      <affiliation>Gaziosmanpasa Univ, Fac Art &amp; Sci, Dept Chem, TR-60240 Tokat, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Okten, Salih</creatorName>
      <givenName>Salih</givenName>
      <familyName>Okten</familyName>
      <affiliation>Gaziosmanpasa Univ, Fac Art &amp; Sci, Dept Chem, TR-60240 Tokat, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Tutar, Ahmet</creatorName>
      <givenName>Ahmet</givenName>
      <familyName>Tutar</familyName>
      <affiliation>Sakarya Univ, Fac Art &amp; Sci, Dept Chem, TR-54187 Adapazan, Turkey</affiliation>
    </creator>
  </creators>
  <titles>
    <title>Efficient And Selective Synthesis Of Quinoline Derivatives</title>
  </titles>
  <publisher>Aperta</publisher>
  <publicationYear>2008</publicationYear>
  <dates>
    <date dateType="Issued">2008-01-01</date>
  </dates>
  <resourceType resourceTypeGeneral="Text">Journal article</resourceType>
  <alternateIdentifiers>
    <alternateIdentifier alternateIdentifierType="url">https://aperta.ulakbim.gov.tr/record/43451</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsIdenticalTo">10.1016/j.tet.2008.08.018</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 bromination reaction of 1,2,3,4-tetrahydroquinoline (7) was investigated by NBS and molecular bromine. One-pot synthesis is described for synthetically valuable 4,6,8-tribromoquinoline (3) and 6,8-dibromo-1,2,3,4-tetrahydroquinoline (6) on bromination of 1,2,3,4-tetrahydroquinoline (7) in efficient yields (75 and 90%, respectively). 6-Bromo- (4) and 6,8-dibromo-1,2,3,4-tetrahydroquinolines (6) were converted to 6-bromo- (1) and 6,8-dibromo quinolines (2), respectively, by aromatization with DDQ in 83 anti 77% yields, respectively. Several novel trisubstituted quinoline derivatives were efficiently prepared via lithium-halogen exchange reactions of tribromide 3. Treatment of 4,6,8-tribromoquinoline with BuLi followed by quenching with electrophiles [Si(CH3)(3)Cl, S-2(CH3)(2), I-2] regioselectively proceeded at C-4 and C-8 sites and afforded corresponding 4,8-disubstituted-6-bromoquinolines. Similarly, lithiation oh tribromide 3 followed by addition of water to the intermediate produced 6-bromoquinoline in 65% yield. Copper induced nucleophile substitution of tribromide 3 with NaOMe afforded 4,6,8-trimethoxyquinoline (17) in 60% yield. (C) 2008 Elsevier Ltd. All rights reserved.</description>
  </descriptions>
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