Studies on 1-Azabicyclo Compounds. XXVI. Synthesis of Ten-membered Ring Amines from 9a-Cyanomethyl-, 9a-Ethoxycarbonylmethyl-, and 1-Ethoxycarbonyl-octahydroquinolizine

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概要

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• Quaternization of 9a-cyanomethyl- and 9a-ethoxycarbonylmethyl-octahydroquinolizine (VI and XI) with methyl iodide afforded cis (VIIa and XIIa) and trans methiodides (VIIb and XIIb), respectively. On treatment with lithium in liquid ammonia, the methiodides (VIIa, XIIa, and XXIV) gave the ten-membered ring amines (VIII, XIII, and XXV), respectively, in moderate yields, however, the methiodide (XXIX) gave only the demethylated product (XXVIII). And the methiodide (VIIa) yielded also the decyanated amines (IX and X) as the by-products. The formation of the ten-membered ring amines (VIII, XIII, and XXV) was proved to proceed as shown in Chart 5 via the unsaturated ten-membered ring amines (XVII, XVIII, and XXX), which were actually derived from the methiodides (VIIa, XIIa, and XXIV), respectively. On the other hand, treatment of VIIa and XIIa with sodium ethoxide afforded the endocyclic olefinic ring amines (XV and XVI), which were shown to be obtained by isomerization of the initially formed exocyclic olefinic ring amines (XVII and XVIII), respectively.

• 社団法人日本薬学会の論文
• 1975-10-25

著者

• 加藤 日出男

  北陸製薬株式会社

• 越中 栄一

  Research and Development Division, Hokuriku Seiyaku Co., Ltd.,

• 越中 栄一

  Research And Development Division Hokuriku Seiyaku Co. Ltd.

• 荒田 義雄

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 花岡 美代次

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 花岡 美代次

  金沢大学薬学部

• 西川 公康

  Research Laboratories, Hokuriku Seiyaku Co., Ltd.

• 花岡 美代次

  Faculty Of Pharmaceutical Sciences Osaka University

• 花岡 美代次

  Faculty Of Pharmaceutical Sciences Kanazawa University

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