College of Chemistry, Chemical Engineering and Materials Science, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Normal University, Jinan, 250014, China.
Jilin Province Key Laboratory of Organic Functional Molecular Design and Synthesis, Department of Chemistry, Northeast Normal University, Changchun, 130024, China.
Angew Chem Int Ed Engl. 2017 Feb 6;56(7):1805-1809. doi: 10.1002/anie.201611024. Epub 2017 Jan 12.
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 C-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.
发展了一种银催化的芳基和杂芳基异氰与α-取代异氰基乙酰胺的化学选择性[4+2]环加成反应，用于方便、高效地合成 2-氨基喹诺酮、萘啶和菲咯啉。根据 C 标记实验，提出了该多步串联反应的机理，其中两个不同异氰的前所未有的化学选择性杂二聚生成α-酰胺基烯亚胺中间体，然后经历 1,3-氨基迁移形成α-亚氨酰基烯酮，接着进行 6π电环化。
