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Synthesis 2021; 53(14): 2494-2502
DOI: 10.1055/a-1399-3823
DOI: 10.1055/a-1399-3823
paper
N-Acylbenzotriazoles as Proficient Substrates for an Easy Access to Ureas, Acylureas, Carbamates, and Thiocarbamates via Curtius Rearrangement Using Diphenylphosphoryl Azide (DPPA) as Azide Donor
The authors sincerely thank the Science and Engineering Research Board (SERB), New Delhi (Grant No. EMR/2016/001123) and the Council of Scientific and Industrial Research (CSIR), New Delhi [Scheme No. 02(0345)/19/EMR-II] for funding. M.S.Y. and A.K.A. acknowledge CSIR for fellowships (SRF), while S.K.S. thanks the University Grants Commission (UGC) for a JRF.
This manuscript is dedicated to the late Prof. Alan R. Katritzky for his notable contributions to benzotriazole chemistry.
Abstract
A diverse range of ureas, N-acylureas, carbamates, and thiocarbamates has been synthesized in good to excellent yields by reacting N-acylbenzotriazoles individually with amines or amides or phenols or thiols in the presence of diphenylphosphoryl azide (DPPA) as a suitable azide donor in anhydrous toluene at 110 °C for 3–4 hours. In this route, DPPA was found to be a good alternative to trimethylsilyl azide and sodium azide for the azide donor in Curtius degradation. The high reaction yields, one-pot and metal-free conditions, straightforward nature, easy handling, use of readily available reagents, and in many cases avoidance of column chromatography are the notable features of the devised protocol.
Key words
N-acylbenzotriazoles - N-acylureas - benzotriazoles - Curtius rearrangement - diphenylphosphoryl azide - carbamates - thiocarbamates - ureasSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1399-3823. Included are copies of 1H and 13C NMR spectra for all developed ureas and their derivatives, carbamates, and thiocarbamates.
- Supporting Information
Publication History
Received: 13 January 2021
Accepted after revision: 24 February 2021
Accepted Manuscript online:
24 February 2021
Article published online:
16 March 2021
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