Silver-Catalyzed Chemoselective [4+2] Annulation of Two Isocyanides: A General Route to Pyridone-Fused Carbo- and Heterocycles
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- 作者：Zhongyan Hu ; Jinhuan Dong ; Yang Men ; Zhichen Lin ; Jinxiong Cai and Prof. Xianxiu Xu
- 刊名：Angewandte Chemie International Edition
- 出版年：2017
- 出版时间：February 6, 2017
- 年：2017
- 卷：56
- 期：7
- 页码：1805-1809
- 全文大小：2040K
- ISSN：1521-3773
文摘
A silver-catalyzed chemoselective [4+2] annulation of aryl and heteroaryl isocyanides with α-substituted isocyanoacetamides was developed for the facile and efficient synthesis of 2-aminoquinolones, naphthyridines, and phenanthrolines. A mechanism for this multistep domino reaction is proposed on the basis of a 13C-labeling experiment, according to which an unprecedented chemoselective heterodimerization of two different isocyanides generates an α-amidoketenimine intermediate, which undergoes 1,3-amino migration to form an α-imidoylketene, followed by 6 π electrocyclization.