Silver-Catalyzed Isocyanide-Isocyanide [3+2] Cross-Cycloaddition Involving 1,2-Group Migration: Efficient Synthesis of Trisubstituted lmidazoles

详细信息    查看全文

• 作者：Hongwei Wang ; Dr. Rapolu Kiran Kumar ; Yang Yu ; Dr. Lin Zhang ; Zhaohong Liu ; Dr. Peiqiu Liao and Prof. Xihe Bi
• 刊名：Chemistry – An Asian Journal
• 出版年：2016
• 出版时间：October 20, 2016
• 年：2016
• 卷：11
• 期：20
• 页码：2841-2845
• 全文大小：923K
• ISSN：1861-471X

文摘

Imidazole ring is an important five-membered aromatic heterocycle that is widely present in natural products and synthetic molecules. The isocyanide–isocyanide [3+2] cross-cycloaddition reaction constitutes a straightforward method to access imidazoles starting from the easily available chemicals. So far, only three successive reports are known and all lead to the formation of 1,4-disubstituted imidazoles. Here, we report the first isocyanide–isocyanide [3+2] cross-cycloaddition reaction allowing for the formation of 1,4,5-trisubstituted imidazoles under silver catalysis. An unexpected 1,2-migration of sulfonyl, alkoxycaybonyl, and carbamoyl groups took place during the cyclization process that is responsible for the formation of trisubstituted imidazoles. This report displayed a mechanistically novel synthetic method toward a variety of imidazole derivatives, which are otherwise difficult to access by conventional methods.