Studies on Tertiary Amine Oxides. LXXIII. Substitution of Aromatic N-Oxides with Radicals produced from Azo Compounds
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概要
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Treatment of quinoline 1-oxide (1a) with α, α'-azobisisobutyronitrile (AIBN) ordimethyl α, α'-azobisisobutyrate in boiling benzene for 5 h affords 2-(1-cyano-1-methylethyl) quinoline (2a) or 2-(1-methoxycarbonyl-1-methylethyl) quinoline (4) in 31.9 or 24.9% yield, respectively, accompanied with a small amount of quinoline in each case. The 1-oxides of lepidine, 3,2'-diquinolyl and 4-nitroquinoline (1c, 1d and 1e), and isoquinoline 2-oxide (6) similarly react with AIBN to produce the corresponding α-substituted products (2c, 2d, 2e and 7). The reaction of pyridine 1-oxide (8) gives not only the 2-substituted pyridine (9 : 1.5%) but also the 4-substituted one (10 : 3.0%). On the other hand, the reactions of 1a and 6 with phenylazotriphenylmethane in boiling benzene afford the α-phenyl N-oxides (12 : 17.2% and 14 : 34.5%) and their deoxygenated products (13 : 3.5% and 15 : 2.9%).
- 公益社団法人日本薬学会の論文
- 1981-11-25
著者
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佐伯 清太郎
Faculty Of Pharmaceutical Sciences Kyushu University
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浜名 政和
Faculty Of Pharmaceutical Sciences Kyushu University
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遠藤 敏廉
Faculty Of Pharmaceutical Sciences Kyushu University
関連論文
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