Quinoxaline誘導体に関する研究(第19報)ジメチルスルホキシド中でのシアン化カリウムの存在下における2-(Methylsulfonyl)-quinoxalineとケトンとの反応について

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Reaction of 2-(methylsulfonyl)quinoxaline (I) and acetophenone (IIIa) in dimethyl sulfoxide, in the presence of potassium cyanide, at 100° results in the formation of 2-pheny1furo[2,3-b]quinoxaline (VIa) accompanying 2-quinoxalinecarbonitrile (IV) and 2,3-quinoxalinedicarbonitrile (V). In order to examine the process of formation of VIa, the same reaction was carried out with IV or V in place of I, and VIa was formed in either case, as well as by the application of potassium cyanide to 2-(2-quinoxalinyl)-acetophenone (VIIa). Therefore, formation of VIa cannot be concluded as a single process. The use of propiophenone (IIIb) as the ketone gave 3-methyl-2-phenylfuro-[2,3-b] quinoxaline (VIb). The same reaction with ketones was carried out with 2-chloroquinoxaline (II) in place of I, and V was obtained in all cases. In addition, VIb was obtained from IIIb and 3-ethyl-2-phenylfuro[2,3-b]quinoxaline (VIc) from butyrophenone (IIIc). In these reactions, yield of furo[2,3-b]quinoxaline derivatives was extremely low, and it seems better to use the reaction of 2,3-dichloroquinoaline (IX) with various ketones in benzene, in the presence of sodium amide, ^<3)> to obtain such derivatives, but this reaction can also be carried out in dimethyl sulfoxide, in the presence of potassium cyanide ; for example, VIb is obtained from IX and IIIb.
公益社団法人日本薬学会の論文
1975-07-25