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

This manuscript is dedicated to (Late) Prof. Alan R Katritzky for his contribution to benzotriazole chemistry.

Abstract

The good leaving tendency of the benzotriazole moiety has been exploited for the synthesis of symmetric, unsymmetric, N-acyl, and cyclic ureas in good yields from N-acylbenzotriazoles by treating the latter with various amines in the presence of TMSN₃/Et₃N in a sealed tube. The salient features of the devised protocol includes the high-yield, mild, metal-free, one-pot reaction conditions, and short reaction time. Furthermore, in many cases, no column chromatography is required for the purification.

Key words

ureas - benzotriazole - Curtius rearrangement - N-acylbenzotriazole - introduction

• References

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