1 Ocak 2008 Dergi makalesi Açık Erişim

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

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  "@context": "https://schema.org/", 
  "@id": 43451, 
  "@type": "ScholarlyArticle", 
  "creator": [
    {
      "@type": "Person", 
      "affiliation": "Gaziosmanpasa Univ, Fac Art & Sci, Dept Chem, TR-60240 Tokat, Turkey", 
      "name": "Sahin, Ayse"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Gaziosmanpasa Univ, Fac Art & Sci, Dept Chem, TR-60240 Tokat, Turkey", 
      "name": "Cakmak, Osman"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Gaziosmanpasa Univ, Fac Art & Sci, Dept Chem, TR-60240 Tokat, Turkey", 
      "name": "Demirtas, Ibrahim"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Gaziosmanpasa Univ, Fac Art & Sci, Dept Chem, TR-60240 Tokat, Turkey", 
      "name": "Okten, Salih"
    }, 
    {
      "@type": "Person", 
      "affiliation": "Sakarya Univ, Fac Art & Sci, Dept Chem, TR-54187 Adapazan, Turkey", 
      "name": "Tutar, Ahmet"
    }
  ], 
  "datePublished": "2008-01-01", 
  "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.", 
  "headline": "Efficient and selective synthesis of quinoline derivatives", 
  "identifier": 43451, 
  "image": "https://aperta.ulakbim.gov.tr/static/img/logo/aperta_logo_with_icon.svg", 
  "license": "http://www.opendefinition.org/licenses/cc-by", 
  "name": "Efficient and selective synthesis of quinoline derivatives", 
  "url": "https://aperta.ulakbim.gov.tr/record/43451"
}