ピラツォロン誘導体の合成研究(第38報)(1R, 4S)-3-Diazobornane-2-oneと活性アセチレンとのCycloadditionにおける[1,5]Sigmatropic転位について

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概要

• 論文の詳細を見る

• (1R, 4S)-3-Diazobornane-2-one was reacted with dimethyl acetylenedicarboxylate and methyl propiolate to give (4S, 7R)-4,7-methano-8H-pyrazolo [1,5-a] azepines (3a, b) (5R, 8S)-5,8-methano-1H, 4H-cycloheptapyrazole (5) via spiropyrazole intermeadiate (6). The reaction from 6 to 3a, b and 5 is interpreted as a [1,5] sigmatropic acyl rearrangement. Compound 3a was converted to (8R, 11S)-8,11-methano-7H-benzo [3,4] pyrazolo [1,5-a]-azepine (12) and (8R, 11S)-8,11-methano-7H-pyridazino [4', 5' : 4,3] pyrazolo [1,5-a] azepine (16). Treatment of 3a, b with sodium methoxide in methanol resulted in cleavage of amido linkage to yield (1R, 3S)-(pyrazol-5-yl) cyclopentanes (17a, b).

• 公益社団法人日本薬学会の論文
• 1979-07-25

著者

• 織田 範一

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 伊藤 磯雄

  名古屋市立大学薬学部

• 織田 範一

  名古屋市立大学薬学部

• 永井 慎一

  名古屋市立大学薬学部

• 織田 範一

  Faculty Of Pharmaceutical Sciences Nagoya City University

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