Abstract The cyclization of cis-2-(2-azidophenyl)-1-benzyl-3-ethoxycarbonylaziridines and trans-2-(2-azidophenyl)-3-nitrocyclopropane-1,1-dicarboxylates yielded the respective aziridino[2,3-c]quinolin-2-ones and cyclopropa[c]quinolin-2-ones. Ring-opening of the aziridine-fused species under silica gel catalysis provided 3-aminoquinolin-2-ones whereas the ring-expansion of the cyclopropane-fused derivatives by the action of sodium hydride gave 1-benzazepin-2-ones, in both cases in a regioselective manner. A computational study using DFT methods revealed that the mechanism for the transformation of cyclopropa[c]quinolin-2-ones into 1-benzazepin-2-ones involves the initial deprotonation step of its amide function followed by two pericyclic events: a 6π-electrocyclic ring opening and a subsequent [1,5]-H shift.

中文翻译：

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通过三元环的区域选择性断裂释放氮丙啶和环丙烷稠合的喹啉-2-酮的合成潜力

摘要 cis-2-(2-azidophenyl)-1-benzyl-3-ethoxycarbonylaziridines 和 trans-2-(2-azidophenyl)-3-nitrocyclopropane-1,1-dicarboxylates 环化生成各自的氮丙啶基[2,3- c]quinolin-2-ones 和 cyclopropa[c]quinolin-2-ones。在硅胶催化下氮丙啶稠合物质的开环提供了 3-氨基喹啉-2-酮，而在这两种情况下，环丙烷稠合衍生物在氢化钠的作用下的扩环得到 1-苯并氮杂-2-酮以区域选择性的方式。使用 DFT 方法的计算研究表明，将 cyclopropa[c]quinolin-2-ones 转化为 1-benzazepin-2-ones 的机制涉及其酰胺功能的初始去质子化步骤，然后是两个周环事件：6π-电环开环和随后的 [1,5]-H 位移。