Synthesis of Spiro[benzo[d][1,3]oxazine-4,4′-isoquinoline]s via [4+1+1] Annulation of N-Aryl Amidines with Diazo Homophthalimides and O2,Organic Letters

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Synthesis of Spiro[benzo[d][1,3]oxazine-4,4′-isoquinoline]s via [4+1+1] Annulation of N-Aryl Amidines with Diazo Homophthalimides and O2
Organic Letters ( IF 4.9 ) Pub Date : 2022-02-07 , DOI: 10.1021/acs.orglett.1c04193
Qianting Zhou ₁ , Xia Song ₁ , Xinying Zhang ₁ , Xuesen Fan ₁

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Synthesis of spiro[benzo[d][1,3]oxazine-4,4′-isoquinoline]s through a unique [4+1+1] annulation of N-aryl amidines with diazo homophthalimides and O₂ is presented. This unprecedented spirocyclization reaction features readily obtainable substrates, structurally and pharmaceutically attractive products, a cost-free and clean oxygen source, sustainable reaction medium, tolerance of a broad spectrum of functional groups, and an interesting reaction mechanism based on sequential C(sp²)–H/C(sp³)–H bond cleavage and oxygen insertion.

中文翻译：

N-芳基脒与重氮同邻苯二甲酰亚胺和 O2 的 [4+1+1] 环化合成螺[苯并[d][1,3]oxazine-4,4'-isoquinoline]s

介绍了通过N-芳基脒与重氮高邻苯二甲酰亚胺和 O ₂的独特 [4+1+1] 环化合成螺[苯并[ d ][1,3]恶嗪-4,4'-异喹啉]s 。这种前所未有的螺环化反应具有易于获得的底物、结构和药学上有吸引力的产品、免费且清洁的氧源、可持续的反应介质、广泛的官能团耐受性以及基于连续 C(sp ² )的有趣反应机制–H/C(sp ³ )–H 键断裂和氧插入。

更新日期：2022-02-07

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