Organic Chemistry Portal



An Improved Synthesis of Urea Derivatives from N-Acylbenzotriazole via Curtius Rearrangement

Anoop S. Singh, Anand K. Agrahari, Sumit K. Singh, Mangal S. Yadav, Vinod K. Tiwari*

*Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi, 22100, India, Email:

A. S. Singh, A. K. Agrahari, S. K. Singh, M. S. Yadav, V. K. Tiwari, Synthesis, 2019, 51, 3443-3450.

DOI: 10.1055/s-0039-1689937

see article for more reactions


The good leaving group ability of the benzotriazole moiety in N-acylbenzotriazoles enables a mild, metal-free synthesis of symmetric, unsymmetric, N-acyl, and cyclic ureas in good yields by treatment with TMSN3/Et3N in the presence of various amines in short reaction time. In many cases, no column chromatography is required for the purification.

see article for more examples

Key Words

ureas, benzotriazole, Curtius rearrangement, N-acylbenzotriazoles

ID: J66-Y2019