Organic Chemistry Portal



Iterative Assembly of Nitrile Oxides and Ynamides: Synthesis of Isoxazoles and Pyrroles

Changwei Chen and Sunliang Cui*

*Institute of Drug Discovery and Design, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China, Email:

C. Chen, S. Cui, J. Org. Chem., 2019, 84, 12157-12164.

DOI: 10.1021/acs.joc.9b01430

see article for more reactions


A Cu(I)-free cyclization of nitrile oxides with terminal ynamides provides isoxazoles, which could engage in another cyclization with internal ynamides in the presence of Au(I) catalyst to deliver pyrroles. Both reactions can be carried out in a two-step, one-pot procedure.

see article for more examples

Key Words


ID: J42-Y2019