抄録
Cyanomethylation of 4, 5, 6, 7-tetrahydro-6, 6-dimethyl-7-oxobenzothiazole (VII), which was prepared from 4, 4-dimethyl-1, 3-cyclohexanedione (I) in several steps, afforded the cyano alcohol (VIII). Compound VIII was treated with lithium aluminum hydride and the resulting amino alcohol (IX) was converted into 7-(2-aminoethyl)-4, 7-dihydro-6, 7-dimethylbenzothiazole (XI) by Wagner-Meerwein rearrangement. Reaction of XI with bromine gave the salt (XII). Treatment of XII with potassium carbonate produced the bridged aziridine (XIII), which was cleaved to the thiazolo [5, 4-f] morphan (4, 5, 6, 7, 8, 9-hexahydro-5, 9-methanothiazolo [4, 5-d] azocine) derivative (XVI) by the action of benzoyl bromide. Dehydrobromination followed by hydrolysis of the benzoyl group led XVI to 5-methyl-9-methylenethiazolo [5, 4-f] morphan (XVIII). Stereospecific hydrogenation of XVIII yielded the 9α-methyl isomer (XIX), whose N-methylation by the Eschweiler-Clarke method completed the synthesis of the desired thiazolo [5, 4-f] morphan (XX). The molecular structure of the oxalate of XIX was established by X-ray analysis.
収録刊行物
-
- CHEMICAL & PHARMACEUTICAL BULLETIN
-
CHEMICAL & PHARMACEUTICAL BULLETIN 31 (5), 1518-1527, 1983
公益社団法人 日本薬学会
- Tweet
キーワード
詳細情報 詳細情報について
-
- CRID
- 1390282679138182912
-
- NII論文ID
- 130003769290
-
- ISSN
- 13475223
- 00092363
-
- 本文言語コード
- en
-
- データソース種別
-
- JaLC
- Crossref
- CiNii Articles
-
- 抄録ライセンスフラグ
- 使用不可