Gold-catalyzed intermolecular reaction of ynamides with 3-indolyl azides via an unexpected 1,2-alkyl migration

Bo Zhou; Ying-Qi Zhang; Xin Liu; Long-Wu Ye

doi:10.1016/j.scib.2017.08.020

Gold-catalyzed intermolecular reaction of ynamides with 3-indolyl azides via an unexpected 1,2-alkyl migration

Sci Bull (Beijing). 2017 Sep 15;62(17):1201-1206. doi: 10.1016/j.scib.2017.08.020. Epub 2017 Aug 19.

Authors

Bo Zhou¹, Ying-Qi Zhang¹, Xin Liu¹, Long-Wu Ye²

Affiliations

¹ State Key Laboratory of Physical Chemistry of Solid Surfaces and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China.
² State Key Laboratory of Physical Chemistry of Solid Surfaces and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China; State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China. Electronic address: longwuye@xmu.edu.cn.

PMID: 36659514
DOI: 10.1016/j.scib.2017.08.020

Abstract

A gold-catalyzed intermolecular reaction of ynamides with 3-indolyl azides via the presumable α-imino gold carbenes has been developed, providing an alternative and efficient way for the synthesis of valuable 3-amino-β-carbolines in generally good to excellent yields. Importantly, this new protocol involves an unexpected 1,2-alkyl migration pathway.

Keywords: Cyclization; Gold; Heterocycles; Migration; Tandem reaction.