Azamorphinan and Related Compounds. II. Synthesis of 3-Methoxy-9-azamorphinan Derivatives : Studies on the Syntheses of Heterocyclic Compounds. CCCXIX
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概要
- 論文の詳細を見る
In order to examine an analgesic activity of azamorphinan derivatives, 3-methoxy-9-azamorphinan (XII) was synthesized as follows. Reduction of octahydrocinnoline derivatives (VIIIa and VIIIb), which were obtained by condensation of 2-(3-methoxyphenyl)-cyclohexanone-2-acetic acid (VI) with hydrazine or benzylhydrazine, with lithium aluminum hydride afforded the corresponding decahydrocinnoline derivatives (IXa and IXb). Pictet-Spengler reaction of IXb gave N-benzyl-3-methoxy-9-azamorphinan (XIV), but cyclization of IXa failed. Therefore, ring-closure of Xa, which was obtained by catalytic hydrogenation of VIIIa, with HOCH_2SO_3Na, followed by lithium aluminum hydride reduction of XI, afforded the compound (XII). This compound (XII) was also obtained by debenzylation of XIV. Furthermore, N-alkylation of XII at the N_<17>-position with methyl, acetyl, allyl, β-phenethyl and cyclopropylmethyl halides gave the corresponding compounds (I, XIII, XVI, XV, and XVII), respectively.
- 公益社団法人日本薬学会の論文
- 1969-06-25
著者
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亀谷 哲治
Pharmaceutical Institute, Tohoku University School of Medicine
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我妻 永利
グレラン製薬株式会社研究所
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亀谷 哲治
Pharmaceutical Institute Medical Faculty University Of Osaka
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我妻 永利
Research Laboratories, Grelan Pharmaceutical Co., Ltd.
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