Oxygen-Promoted 6-endo-trig Cyclization of β,γ-Unsaturated Hydrazones/Ketoximes with Diazonium Tetrafluoroborates for Pyridazin-4(1H)-ones/Oxazin-4(1H)-ones,Organic Letters

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Oxygen-Promoted 6-endo-trig Cyclization of β,γ-Unsaturated Hydrazones/Ketoximes with Diazonium Tetrafluoroborates for Pyridazin-4(1H)-ones/Oxazin-4(1H)-ones
Organic Letters ( IF 4.9 ) Pub Date : 2023-08-15 , DOI: 10.1021/acs.orglett.3c02073
Zhenjie Qi ₁ , Simiaomiao Wen ₂ , Zhao Liu ₂ , Dongfang Jiang ₂

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An oxidative 6-endo-trig cyclization and [2 + 2] cycloaddition of β,γ-unsaturated hydrazones/ketoximes and diazonium tetrafluoroborates for a synthetic strategy to pyridazin-4(1H)-ones/oxazin-4(1H)-ones under metal-free conditions is presented in a one-pot procedure. This protocol features excellent functional group tolerance and remarkable regioselectivity. A mechanistic study has been verified via ¹⁸O labeling and the H₂¹⁸O labeling method, in which O₂ acts as both a reaction component and an oxidant.

中文翻译：

氧促进 6-endo-trig 环化 β,γ-不饱和腙/酮肟与四氟硼酸重氮生成哒嗪-4(1H)-酮/恶嗪-4(1H)-酮

β,γ-不饱和腙/酮肟和四氟硼酸重氮盐的氧化6-内三环化和[2 + 2]环加成合成哒嗪-4(1 H)-酮/恶嗪-4(1 H )-在无金属条件下的产物以一锅法进行呈现。该方案具有优异的官能团耐受性和显着的区域选择性。^通过18 O 标记和 H ₂¹⁸ O 标记方法验证了机理研究，其中 O ₂既充当反应组分又充当氧化剂。

更新日期：2023-08-15

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