Chemoselective Double Annulation of Two Different Isocyanides: Rapid Access to Trifluoromethylated Indole-Fused Heterocycles,Organic Letters

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Chemoselective Double Annulation of Two Different Isocyanides: Rapid Access to Trifluoromethylated Indole-Fused Heterocycles
Organic Letters ( IF 4.9 ) Pub Date : 2017-09-13 00:00:00 , DOI: 10.1021/acs.orglett.7b02582
Yuelei Gao ₁ , Zhongyan Hu ₁ , Jinhuan Dong ₂ , Jun Liu ₁ , Xianxiu Xu _{1,

2}

Affiliation

An unprecedented chemoselective double annulation of α-trifluoromethylated isocyanides with o-acylaryl isocyanides has been developed. This new reaction provides a rapid, efficient, and complete atom-economic strategy for the synthesis of trifluoromethylated oxadiazino[3,2-a]indoles in a single operation from readily available starting materials. Isocyanide insertion into C═O double bonds is disclosed for the first time as indicated by the results of ¹⁸O-labeling experiment. A mechanism for this domino reaction is proposed involving chemoselective heterodimerization of two different isocyanides, followed by indole-2,3-epoxide formation and rearrangement.

中文翻译：

两种不同异氰酸酯的化学选择性双环：快速获得三氟甲基化的吲哚杂环化合物。

已经开发出空前的α-三氟甲基化异氰酸酯与邻酰基芳基异氰酸酯的化学选择性双环。该新反应提供了快速，有效和完整的原子经济策略，可通过一次操作从容易获得的起始原料合成三氟甲基化的恶二嗪并[3,2- a ]吲哚。由¹⁸ O-标记实验的结果表明，异氰酸酯首次插入C = O双键。提出了这种多米诺反应的机制，其中包括两种不同异氰酸酯的化学选择性异二聚化，然后是吲哚-2,3-环氧化物的形成和重排。

更新日期：2017-09-13

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