Thiazole Analogs of Benzomorphans. II. Synthesis of Novel Thiazolo [5,4-f] morphans

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概要

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• 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.

• 1983-05-25

著者

• 三橋 監物

  Faculty of Pharmaceutical Sciences, University of Toyama

• 山口 啓一

  Faculty Of Pharmaceutical Sciences Chiba University

• 山口 啓一

  Faculty Of Pharmaceutidal Sciences Chiba University

• 坂井 進一郎

  Faculty Of Pharmaceutical Sciences Chiba University

• 勝浦 公男

  Faculty Of Pharmaceutical Sciences Josai University

• 三橋 監物

  Faculty Of Pharmaceutical Sciences Josai University

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