Studies on Tertiary Amine Oxides. XXXIX. Reactions of Aromatic N-Oxides with Indoles in the Presence of Acylating Agents
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概要
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Indole (II) was found to react as an aromatic analog of enamine with acyl-adducts of quinoline 1-oxide (I) and ethyl nicotinate 1-oxide (VI) under refluxing condition in chloroform, and 3-(2-quinolyl) indole (III) and ethyl 6-(3-indolyl) nicotinate (VII) were obtained, respectively, but no reaction occured with pyridine 1-oxide. Benzoyl chloride was most effective as an acylating agent. 1-Methylindole (VIII) underwent similar reactions. The reaction with I gave 1-methyl derivative of III (IX) as well as 4-quinolyl compound (X). From the reaction with 2-chloroquinoline 1-oxide (XI), 1-methyl-3-(2-chloro-4-quinolyl) indole (XIII) and 1-benzoyloxy-2-hydroxy-4-(1-methyl-3-indolyl)-1,4-dihydroquinoline (XIV) were produced, the isolation of XIV being significant from the mechanistic view point. 4-Chloroquinoline 1-oxide and VIII afforded 2-quinolyl compound (XVI). Further 2-phenylindole was shown to react with I under similar conditions, but skatole resisted the reaction.
- 公益社団法人日本薬学会の論文
- 1970-09-25
著者
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熊懐 稜丸
Faculty of Pharmaceutical Sciences, Setsunan University
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浜名 政和
Faculty of Pharmaceutical Sciences, Kyushu University
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熊懐 稜丸
Faculty Of Pharmaceutical Sciences Setsunan University
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熊懐 稜丸
Faculty Of Pharmaceutical Sciences Kyushu University:(present Address)tokyo College Of Pharmacy Kash
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浜名 政和
Faculty Of Pharmaceutical Sciences Kyushu University
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