Facile Synthesis and Ring Transformations of a Spiro-[cyclobutene-1,2'(1H)-quinoxaline]

概要

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The reaction of 3-(N, N-dimethylcarbamoyl) furo [2,3-b] quinoxaline (2) with ethyl cyanoacetate in sodium ethoxide-ethanol occurred with ring transformation to give 4-cyano-2-ethoxy-carbonyl-3-hydroxy-3'-oxo-3', 4'-dihydrospiro [2-cyclobutene-1,2'(1H)-quinoxaline] (5). When 5 was refluxed in acetic acid and in N, N-dimethylformamide, it afforded 2-cyano-3-hydroxy-3'-oxo-3', 4'-dihydrospiro [2-cyclobutene-1,2'(1H)-quinoxaline] (6) and 7-cyano-5,6-dihydro-6,10-dioxo-8-hydroxy-10H-pyrido [1,2-a] quinoxaline (9), respectively. Refluxing of 5 with hydrazine dihydrochloride and with o-phenylenediamine dihydrochloride in acetic acid also induced ring transformation to produce 6-(3-oxo-3,4-dihydroquinoxalin-2-yl)-3-amino-5-hydroxy-7-oxo-1,2-dihydro-1,2-diazepine hydrochloride (12a) and 16-amino-1,8-dioxo-1,2,8,10-tetrahydro-quinoxalino [1', 2' : 1,2] pyrido [4,3-b] [1,5] benzodiazepine hydrochloride (13a), respectively.
社団法人日本薬学会の論文
1984-09-25