An uncommon aza-Diels-Alder reaction of electron-deficient azoalkenes and electron-deficient 3-phenacylideneoxindoles was successfully developed for convenient construction of the heterocyclic spirooxindoles. The aza-Diels-Alder reaction of azoalkenes, which were in situ generated from base dehydrohalogenation of α-halogeno N-acylhydrazones, with 3-methyleneoxindoles afforded functionalized spiro[indoline-3,3′-pyridazin]-2-ones in good yields and with high diastereoselectivity. Under same reaction conditions, the base promoted reaction of α-halogeno N-acylhydrazones and 3-aryliminoindolin-2-ones in DCM at room temperature resulted in functionalized spiro[indoline-3,3'-[1,2,4]triazin]-2-ones in satisfactory yields.

中文翻译：

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缺电子偶氮烯烃与缺电子 3-phencaylideneoxindoles 和 3-aryliminooxindol-2-ones 的 Aza-Diels-Alder 反应

为方便构建杂环螺氧吲哚，成功开发了缺电子偶氮烯烃和缺电子 3-苯亚甲基吲哚的罕见氮杂-狄尔斯-阿尔德反应。由 α-卤代 N-酰基腙的碱脱卤化氢原位产生的偶氮烯烃与 3-亚甲氧吲哚的 aza-Diels-Alder 反应以良好的收率提供了官能化的螺[二氢吲哚-3,3'-哒嗪]-2-酮并且具有很高的非对映选择性。在相同的反应条件下，碱促进α-卤代N-酰基腙和3-aryliminoindolin-2-ones在室温下在DCM中反应产生功能化的螺[indoline-3,3'-[1,2,4]triazin] -2 的产量令人满意。