Quinoxaline誘導体に関する研究(第21報) : 2-置換Furo[2,3-b]-quinoxaline, 2-置換Pyrrolo[2,3-b]quinoxalineの合成

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Examinations were made on the following reactions for the synthesis of 2-substituted furo [2,3-b] quinoxaline (I) : (a) Application of alkali to 1-(3-chloro-2-quinoxalinyl)-2-alkanone (IV) in dioxane, (b) refluxing of 1-(3,4-dihydro-3-oxo-2-quinoxalinyl)-2-alkanone (V) in acetic anhydride, in the presence of conc. sulfuric acid, (c) heating of V with polyphosphoric acid, and (d) application of phosphoryl chloride to IV or V. It was found that method (c) was the best and that 2-chloro-3-(2-chloro-1-alkenyl) quinoxaline (VIII) is the main product obtained by method (d). 2-Substituted 1-phenylpyrrolo [2,3-b] quinoxaline (II) is obtained by heating IV with aniline, and 2-substituted pyrrolo [2,3-b] quinoxaline (III) is obtained by the application of sodium amide to 1-(3-methoxy-2-quinoxalinyl)-2-alkanone (X), in the presence of methyl ethyl ketone.
公益社団法人日本薬学会の論文
1977-07-25