Metal‐Free Cyclization of ortho‐Nitroaryl Ynamides and Ynamines towards Spiropseudoindoxyls,Angewandte Chemie International Edition

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Metal‐Free Cyclization of ortho‐Nitroaryl Ynamides and Ynamines towards Spiropseudoindoxyls
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2018-04-16 , DOI: 10.1002/anie.201800340
Niels Marien ₁ , B. Narendraprasad Reddy ₁ , Freija De Vleeschouwer ₂ , Steven Goderis ₃ , Kristof Van Hecke ₄ , Guido Verniest _{1,

5}

Affiliation

An efficient metal‐free cascade reaction between 1‐dibromovinyl‐2‐nitro‐substituted arenes and secondary amines results in the formation of polycyclic pseudoindoxyls in a single step. The reaction mechanism leading to these fused ring systems was investigated, and is believed to involve the initial formation of nitroarylated ynamines/ynamides. These intermediates cycloisomerize towards N‐alkenyl‐tethered 2‐aminoisatogens via a carbene intermediate as demonstrated by QTAIM (quantum theory of atoms in molecules) and ELF (electron localization function) analysis. A subsequent intramolecular dipolar cycloaddition afforded the title compounds.

中文翻译：

邻硝基硝基芳基亚胺和亚胺向螺假吲哚酚的无金属环化。

1-二溴乙烯基-2-硝基取代的芳烃与仲胺之间的有效无金属级联反应可一步完成多环拟吲哚酚的形成。研究了导致这些稠合环系统的反应机理，并认为其涉及硝基芳基化的氨基胺/酰胺的初始形成。这些中间体通过卡宾中间体向N-链烯基拴链的2-氨基异氰酸酯环状异构化，如QTAIM（分子中原子的量子理论）和ELF（电子定位功能）分析所证明。随后的分子内偶极环加成得到标题化合物。

更新日期：2018-04-16

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