化学
醇盐
伊萨丁
烷基
缩合反应
有机化学
苯酰
冷凝
药物化学
组合化学
催化作用
热力学
物理
作者
María S. Shmidt,Isabel A. Perillo,Alicia Camelli,María Alejandra Fernández,María M. Blanco
标识
DOI:10.1016/j.tetlet.2016.01.077
摘要
We present here two new methods based on rearrangement reactions to obtain novel 2-substituted 3-hydroxy-4-oxo-1,4-dihydroquinolines, an important family of heterocycles with potential applications. Alkyl 3-hydroxy-4-oxo-1,4-dihydroquinoline-2-carboxylates were obtained by alkoxide promoted rearrangement of alkyl isatinacetates. A second synthetic route involves the alkoxide promoted reaction of both isatin and N-methylisatin, with alkylating agents having acidic methylenes. This reaction leads to the formation of spiroepoxyoxindoles via Darzens' condensation. When phenacyl bromides are used, the initially obtained benzoyl substituted spiroepoxyoxindoles were smoothly transformed into the corresponding 2-benzoyl-3-hydroxy-4-quinolinones with good to excellent yields.
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