Oxidative Radical Cyclization of N‐methyl‐N‐arylpropiolamide to Isatins via Cleavage of the Carbon‐carbon Triple Bond,Advanced Synthesis & Catalysis

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Oxidative Radical Cyclization of N‐methyl‐N‐arylpropiolamide to Isatins via Cleavage of the Carbon‐carbon Triple Bond
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2018-07-08 , DOI: 10.1002/adsc.201800592
Yan-Yan Liao ₁ , Yong-Chao Gao ₁ , Wenxu Zheng ₁ , Ri-Yuan Tang _{1,

2}

Affiliation

A radical cyclization of N‐methyl‐N‐arylpropiolamide to isatins via an oxidative cleavage of a carbon‐carbon triple bond has been developed. In the presence of oxone and NaNO₂, a variety of N‐methyl‐N‐arylpropiolamides were smoothly transformed into isatins. A nitration reaction proceeded along with the oxidative cyclization; both nitrated and non‐nitrated isatins were obtained in a one‐pot reaction with moderate to good total yields. This is the first example for the synthesis of isatins via the oxidative radical cleavage of a carbon‐carbon triple bond.

中文翻译：

N-甲基-N-芳基丙醇酰胺通过碳-碳三键的裂解被氧化成Isatins的氧化自由基环化。

已开发出通过碳-碳三键的氧化裂解将N-甲基-N-芳基丙醇酰胺自由基环化为靛红的方法。在存在丙酮和NaNO _{2的情况下}，各种N-甲基-N-芳基丙酰胺都可以平稳地转化为靛红。硝化反应与氧化环化一起进行。一锅反应可同时获得硝化和未硝化的靛红，总收率中等至良好。这是通过碳-碳三键的氧化自由基裂解合成Isatin的第一个例子。

更新日期：2018-07-08

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