3-Chloroquinoline-2,4-diones react with cyanide ions in dimethyl formamide to give 3-cyanoquinoline-2,4-diones in small yields due to the strong hindrance of the substituent at the C-3 atom. Good yields can be achieved if the substituent at this position is the methyl group. In the methanol solution, the reaction proceeds by an addition mechanism to form 2-oxo-1a,2,3,7b-tetrahydrooxireno[2,3-c]quinoline-7b-carbonitriles, from which 4-hydroxy-3-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-4-carbonitriles are subsequently formed by opening of the epoxide ring with methanol. Some minor products of these reactions have also been isolated. The ¹H, ¹³C and ¹⁵N NMR spectra of the prepared compounds were measured, and all resonances were assigned using appropriate two-dimensional spectra.

中文翻译：

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叔 2-氯酮与氰离子的反应：应用于 3-氯喹啉二酮

由于 C-3 原子上取代基的强位阻，3-Chloroquinoline-2,4-diones 与二甲基甲酰胺中的氰离子反应生成 3-cyanoquinoline-2,4-diones，产率很小。如果该位置的取代基是甲基，则可以获得良好的收率。在甲醇溶液中，反应通过加成机理进行，生成 2-oxo-1a,2,3,7b-tetrahydrooxireno[2,3- c ]quinoline-7b-carbonitriles，从中生成 4-hydroxy-3-methoxy-随后通过用甲醇打开环氧化物环形成2-氧代-1,2,3,4-四氢喹啉-4-腈。这些反应的一些次要产物也被分离出来。1 H、¹³ C^和15测量制备的化合物的 N NMR 光谱，并使用适当的二维光谱分配所有共振。