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

doi:10.1055/s-0039-1689937

Synthesis, Table of Contents

Synthesis 2019; 51(18): 3443-3450
DOI: 10.1055/s-0039-1689937

paper

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: tiwari_chem@yahoo.co.in Email: Vinod.Tiwari@bhu.ac.in

› Author Affiliations

Abstract

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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

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References

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