Cinnoline誘導体に関する研究(第4報) : 4-(Methylsulfonyl)cinnolineとケトンとの反応についてその2

概要

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Reaction of 4-(methylsulfonyl) cinnoline (I) with various ketones (IIa to IIm) (Chart 1) in the presence of sodium hydroxide solution was carried out. Reaction of I with IIa and IIf gave IIIa and IIIf, respectively Reaction of I with IIb gave IVb, instead of IIIb The route of this reaction was assumed as shown in Chart 3. IVb is also obtained from the reaction of I with IIg or IIh. I and IIc afforded IVc by a similar route as above (Chart 4) and IVc is also obtained from the reaction of I with IIi. Ketones with branched alkyl chain, IId and IIe, did not react with I, while the methyl group in IIj and IIk reacted with I to form IIIj' and IIIk', whose hydrolysis afforded the same IVj (Chart 4). The same reaction had previously been carried out in the presence of sodium amide in benzene, and the same products obtained as in the present reaction were IIIa, IIIf, IV1,and IVm, and a difference in the reaction was observed in the case of other ketones when using sodium hydroxide solution.
公益社団法人日本薬学会の論文
1968-06-25