1 Ocak 2008 Dergi makalesi Açık Erişim

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

Citation Style Language JSON

{
  "DOI": "10.1016/j.tet.2008.08.018", 
  "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.", 
  "author": [
    {
      "family": "Sahin", 
      "given": " Ayse"
    }, 
    {
      "family": "Cakmak", 
      "given": " Osman"
    }, 
    {
      "family": "Demirtas", 
      "given": " Ibrahim"
    }, 
    {
      "family": "Okten", 
      "given": " Salih"
    }, 
    {
      "family": "Tutar", 
      "given": " Ahmet"
    }
  ], 
  "container_title": "TETRAHEDRON", 
  "id": "43451", 
  "issue": "43", 
  "issued": {
    "date-parts": [
      [
        2008, 
        1, 
        1
      ]
    ]
  }, 
  "page": "10068-10074", 
  "title": "Efficient and selective synthesis of quinoline derivatives", 
  "type": "article-journal", 
  "volume": "64"
}