含窒素芳香族複素環N-オキシドに対する酸クロリドおよびシアン化物の反応(第9報)2-Methylquinoline 1-Oxideおよび関連化合物の側鎖炭素へのp-Tolylsulfonyl基の導入反応について

概要

論文の詳細を見る
Reaction of 2-methylquinoline 1-oxide (I_1), 2,4-dimethylquinoline 1-oxide (I_2), 2-ethyl-3-methylquinoline 1-oxide (I_3), and 6-methylphenanthridine 5-oxide (I_4) with methanesulfonyl chloride, p-toluenesulfonyl chloride, p-toluenesulfonyl cyanide, or benzoyl chloride, in the presence of sodium p-toluenesulfinate, was carried out in acetonewater solution at room temperature. This reaction was found to progress in the four following types : 1) Introduction of a p-tolylsulfonyl group into the ring-carbon, accompanied by liberation of oxygen from the N→O group. 2) Introduction of a p-tolylsulfonyl group into the side-chain carbon in the position α to the ring-nitrogen, accompanied by liberation of oxygen from the N→O group. 3) Solely the liberation of oxygen from the N→O group. 4) When benzoyl chloride was used, benzoyloxyl group is introduced into the carbon atom in the methyl group in position α to the ring-nitrogen, accompanied by liberation of oxygen from the N→O group. However, present experimental data were insufficient to give conclusive evidence for conditions favoring the reaction noted in (2) above.
社団法人日本薬学会の論文
1978-11-25