Synthesis of Melanthioidine Derivative by Double Ullmann Reaction (Studies on the Syntheses of Heterocyclic Compounds. CCXXVI)
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概要
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Diastereoisomeric mixture of racemic melanthooioine (I and II), was synthesized by the following procedures. Bischler-Napieralski reaction of the amide (XIII), which was obtained by Schotten-Baumann reaction of 4-hydroxy-3-methoxyphenethylamine zinc chloride (IX) with acid chloride (X), followed by ethoxycarbonylation of the amide (XI) with ethyl chlorocarbonate, afforded the 3,4-dihydroisoquinoline (XIII). Reduction with sodium borohydride of the methiodide (XIV), which was obtained by methylation of XIII with methyl iodide, gave a mixture of 1,2,3,4-tetrahydroisoquinolines, (XV) and (XVI), whose hydrolysis with an alkaline solution afforded the latter compound (XVI). Secondly, double Ullmann reaction of the preceding compound (XVI) afforded a diastereoisomeric mixture of O, O-dibenzylmelanthioidine, which was debenzylated to give a diastereoisomeric mixture of I and II. Therefore, it is of particular interest that the twentymembered ring system as melanthioidine-type compound has been synthesized.
- 社団法人日本薬学会の論文
- 1968-04-25
著者
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亀谷 哲治
Pharmaceutical Institute, Tohoku University School of Medicine
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高野 誠一
Pharmaceutical Institute Tohoku University
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芳賀 清次
Pharmaceutical Institute, Tohoku University School of Medicine
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亀谷 哲治
Pharmaceutical Institute Medical Faculty University Of Osaka
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