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Quinolizidines. I. : Quaternization of the Quinolizidine System : Effect of β, γ-Unsaturation on Stereoselectivity in Methiodide Formation
http://hdl.handle.net/2297/7595
http://hdl.handle.net/2297/7595c445925d-96be-4817-833e-a9a13390f905
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
PE-PR-OHBA-M-144.pdf (1.9 MB)
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| Item type | 学術雑誌論文 / Journal Article(1) | |||||
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| 公開日 | 2017-10-03 | |||||
| タイトル | ||||||
| タイトル | Quinolizidines. I. : Quaternization of the Quinolizidine System : Effect of β, γ-Unsaturation on Stereoselectivity in Methiodide Formation | |||||
| 言語 | ||||||
| 言語 | eng | |||||
| 資源タイプ | ||||||
| 資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
| 資源タイプ | journal article | |||||
| 著者 |
Fujii, Tozo
× Fujii, Tozo× Nohara, Masanobu× Mitsukuchi, Morihiro× Ohba, Masashi× Shikata, Kiyoko× Yoshifuji, Shigeyuki× Ikegami, Shiro |
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| 書誌情報 |
Chemical & pharmaceutical bulletin 巻 23, 号 1, p. 144-156, 発行日 1975-01-25 |
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| ISSN | ||||||
| 収録物識別子タイプ | ISSN | |||||
| 収録物識別子 | 0009-2363 | |||||
| NCID | ||||||
| 収録物識別子タイプ | NCID | |||||
| 収録物識別子 | AA00602100 | |||||
| DOI | ||||||
| 関連タイプ | isIdenticalTo | |||||
| 識別子タイプ | DOI | |||||
| 関連識別子 | 10.1248/cpb.23.144 | |||||
| 出版者 | ||||||
| 出版者 | 日本薬学会 | |||||
| 抄録 | ||||||
| 内容記述タイプ | Abstract | |||||
| 内容記述 | Quaternization of benzo [a] quinolizidine (Ib) with methyl iodide gave a 3.6 : 1 mixture of the cis- (IIb : X=I) and the trans-methiodide (IIIb : X=I). The 9,10-dimethoxy derivative (Ia) also gave the corresponding cis- (IIa : X=I) and trans-methiodide (IIIa : X=I) in a ratio of 3.3 to 1. Treatment of enamines Va, b with methyl iodide furnished the N-methylated product (VIa, b) and the C-methylated product (VIIa, b) in a ratio of 1.2 : 1. Catalytic hydrogenation of VIa, b produced a mixture of the cis- (IIa, b) and the trans-methosalt (IIIa, b) in a rough ratio of 2.8 : 1,whereas that of VIIa, b gave the 1-methylated benzo [a] quinolizidine (VIIIa, b). Compound VIIIa was alternatively prepared from piperidone IX by the Bischler-Napieralski cyclization and subsequent hydrogenation. In the case of the simple quinolizidine system with the simplest β, γ-unsaturation (XV), the quaternization with methyl iodide produced the cis- (XVI) and the trans-methiodide (XVII) almost equally. Repetition of the known methiodide formation of XXVI and hydrogenation of enamine methiodide XIX confirmed their reported high stereoselectivity, and factors responsible for the difference in stereoselectivity between these reactions of the β, γ-unsaturated system and the saturated system have been discussed. At 250° the cis-methiodides (IIa, b, XX) isomerized to the corresponding trans-fused salts (IIIa, b, XXI) to some extent and one may roughly compare the susceptibilities of IIa, IIb, and XX, which decrease in that order. | |||||
| 著者版フラグ | ||||||
| 出版タイプ | VoR | |||||
| 出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||
