Journal
SYNTHESIS-STUTTGART
Volume 53, Issue 14, Pages 2494-2502Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/a-1399-3823
Keywords
N-acylbenzotriazoles; N-acylureas; benzotriazoles; Curtius rearrangement; diphenylphosphoryl azide; carbamates; thiocarbamates; ureas
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Funding
- Science and Engineering Research Board (SERB), New Delhi [EMR/2016/001123]
- Council of Scientific and Industrial Research (CSIR), New Delhi [02(0345)/19/EMR-II]
- CSIR
- University Grants Commission (UGC)
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A diverse range of ureas, N-acylureas, carbamates, and thiocarbamates can be 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 an azide donor. The use of DPPA as an alternative to other azide donors in Curtius degradation allows for high reaction yields under metal-free conditions with easy handling of readily available reagents.
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 degrees 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.
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