Studies on 1,2,3,4-Tetrahydroisoquinolines. V. A Convenient Synthesis of (±)-5,7-Dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline (Racemic TA-073)
スポンサーリンク
概要
- 論文の詳細を見る
A convenient synthetic route to (±)-5,7-dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline (racemic TA-073), an orally active bronchodilator, through the cyclization of the amine 4 or its N-acyl derivative (10b, c) is presented. Catalytic reduction of 4 over 10% Pd-C in EtOH-H_2O in the presence of oxalic acid (6 eq) afforded racemic TA-073 in 65% yield. The acid-catalyzed reaction of 10b, c was also investigated. Cyclization of 10b, c with 1 N HCl (1 eq) in THF gave the corresponding N-acyl enamine 12b, c in quantitative yield. Further treatment of 12b with conc. HCl in THF afforded the pavine derivative 14 in 80% yield. Cyclization of 10b with neat HCOOH, however, resulted in the formation of the isopavine derivative 11b in 80% yield. This result parallels the reported observation by McDonald et al.
- 社団法人日本薬学会の論文
- 1982-09-25
著者
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武田 幹男
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,
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大塚 久男
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.
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綱島 朗
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.
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伊藤 信夫
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.
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伊藤 信夫
Research Laboratories Tanabe Seiyaku Co. Ltd.
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岩隈 建男
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.
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大塚 久男
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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綱島 朗
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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岩隈 建男
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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山田 幸一郎
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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大塚 久雄
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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武田 幹男
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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武田 幹男
田辺製薬株式会社有機化学研究所
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