ピラゾロン誘導体の合成研究(第42報)2-Methyl-1-phenyl-6,7-dihydro-1H, 5H-pyrazolo[5,1-b][1,3]oxazin-8-ium Bromideの合成と鎮痛作用について

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タイトル別名
  • Synthesis of Pyrazolone Derivatives. XLII. Synthesis and Analgesic Activity of 2-Methyl-1-phenyl-6, 7-dihydro-1H, 5H-pyrazolo [5, 1-b] [1, 3] oxazin-8-ium Bromide
  • ピラゾロン誘導体の合成研究-42-2-Methyl-1-phenyl-6,7-dihydro-1H,5H-pyrazolo〔5,1-b〕〔1,3〕oxazin-8-ium Bromideの合成と鎮痛作用について
  • ピラゾロン ユウドウタイ ノ ゴウセイ ケンキュウ 42 2 Methyl 1

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説明

The synthesis of 2-methyl-1-phenyl-6, 7-dihydro-1H, 5H-pyrazolo [5, 1-b] [1, 3] oxazin-8-ium bromide (VII) and its reactions with some nucleophilic reagents were carried out : The reaction of 3-hydroxy-5-methyl-1-phenylpyrazole (IV) with trimethylene bromide in dimethylformamide (DMF) in the presence of potassium carbonate gave VII (86%) and 1, 3-bis (5-methyl-1-phenyl-3-pyrazolyloxy) propane (VIII) (6%). Treatment of VII with 5% aqueous sodium hydroxide solution or sodium hydrosulfide in DMF gave 1-(3-hydroxypropyl)-3-methyl-2-phenyl-3-pyrazolin-5-one (VI) (80%) or 1-(3-hydroxypropyl)-3-methyl-2-phenyl-3-pyrazoline-5-thione (IX) (55%). However, the reaction of VII with sodium p-nitrophenolate or sodium diethyldithiocarbamate gave 3-methyl-1-[3-(p-nitrophenoxy) propyl]-2-phenyl-3-pyrazolin-5-one (X) (74%) or 3-(3-methyl-5-oxo-2-phenyl-3-pyrazolin-1-yl) propyl N, N-diethyldithiocarbamate (XI) (72%).

収録刊行物

  • 薬学雑誌

    薬学雑誌 102 (8), 743-747, 1982

    公益社団法人 日本薬学会

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