Carbazole → 1,6-Dihydrocyclopenta[c]carbazol-3(2H)-one

HRID 1615014ノート

反応式

HRID 1615014 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH2:12][CH2:13][C:14]2=[O:19])([O-])=O.P(OCC)(OCC)OCC.C1C2NC3C(=CC=CC=3)C=2C=CC=1>CCOCC>[CH2:12]1[C:11]2[C:10]3[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[NH:1][C:18]=3[CH:17]=[CH:16][C:15]=2[C:14](=[O:19])[CH2:13]1

参加物

5

反応物 3

HCID 6854CarbazoleHCID 31215Triethyl phosphiteHCID 585449044-(2-Nitrophenyl)indan-1-one

生成物 1

HCID 585448961,6-Dihydrocyclopenta[c]carbazol-3(2H)-one収率 61.8%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
90 °C

実験手順

Compound 45 (5.0 g) was divided into five portions (1.0 g each). P(OEt)3 (per 7 mL) was added to each portion. The resulting product was subjected to argon blow in a flask, heated to 90° C., kept at this temperature for 3 days, then cooled. The carbazole precipitate was diluted with ether. The precipitate was filtered and washed with ether. If the initial biphenyl was present in the filtrate (TLC monitoring, eluent: hexane-ethyl acetate, 1:1), this filtrate was evaporated, then P(OEt)3 was added (1 mL to each flask), and subjected to cyclization for 1 day. The procedure was repeated until the precipitation ceased and TLC showed the absence of the initial biphenyl. Carbazol 46 (2.7 g) was obtained.

後処理

  1. customThe resulting product was subjected to argon blow in a flask
  2. temperaturecooled
  3. filtrationThe precipitate was filtered
  4. washwashed with ether
  5. customthis filtrate was evaporated
  6. additionP(OEt)3 was added (1 mL to each flask)
  7. waitsubjected to cyclization for 1 day
  8. customThe procedure was repeated until the precipitation

出典と根拠

ORDレコード
ord-4229050550824619a455fa06ac061a61
出典データセット
uspto-grants-2014_07
特許番号
US08765738B2

反応ノート

読み込み中…