Synthesis 2021; 53(14): 2494-2502
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
Mangal S. Yadav
,
Sumt K. Singh
,
Anand K. Agrahari
,
Anoop S. Singh
,
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 -
ureas
Supporting 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
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
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