1 Ocak 2008 Dergi makalesi Açık Erişim

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

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        "affiliation": "Gaziosmanpasa Univ, Fac Art & Sci, Dept Chem, TR-60240 Tokat, Turkey", 
        "name": "Sahin, Ayse"
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      {
        "affiliation": "Gaziosmanpasa Univ, Fac Art & Sci, Dept Chem, TR-60240 Tokat, Turkey", 
        "name": "Cakmak, Osman"
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      {
        "affiliation": "Gaziosmanpasa Univ, Fac Art & Sci, Dept Chem, TR-60240 Tokat, Turkey", 
        "name": "Demirtas, Ibrahim"
      }, 
      {
        "affiliation": "Gaziosmanpasa Univ, Fac Art & Sci, Dept Chem, TR-60240 Tokat, Turkey", 
        "name": "Okten, Salih"
      }, 
      {
        "affiliation": "Sakarya Univ, Fac Art & Sci, Dept Chem, TR-54187 Adapazan, Turkey", 
        "name": "Tutar, Ahmet"
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    "description": "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.", 
    "doi": "10.1016/j.tet.2008.08.018", 
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    "journal": {
      "issue": "43", 
      "pages": "10068-10074", 
      "title": "TETRAHEDRON", 
      "volume": "64"
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    "publication_date": "2008-01-01", 
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    "title": "Efficient and selective synthesis of quinoline derivatives"
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