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Synthesis 2019; 51(18): 3443-3450
DOI: 10.1055/s-0039-1689937
DOI: 10.1055/s-0039-1689937
paper
An Improved Synthesis of Urea Derivatives from N-Acylbenzotriazole via Curtius Rearrangement
The authors thank the Science and Engineering Research Board (SERB), Department of Science & Technology, New Delhi (Grant No. EMR/2016/001123) for funding. The authors sincerely thank CISC-Banaras Hindu University (BHU), Varanasi for all the infrastructure and instrument support. A.K.A. and M.S.Y. acknowledge Council of Scientific & Industrial Research (CSIR), New Delhi for Senior and Junior Research Fellowships, and S.K.S. thanks University Grant Commission (UGC), New Delhi for Junior Research Fellowship.Further Information
Publication History
Received: 09 April 2019
Accepted after revision: 14 May 2019
Publication Date:
12 June 2019 (online)
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1689937.
- Supporting Information
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