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Synthesis 2005(18): 3124-3134
DOI: 10.1055/s-2005-916029
DOI: 10.1055/s-2005-916029
PAPER
© Georg Thieme Verlag Stuttgart · New YorkPhosphorylation of Arylureas and Arylcarbamates: A New Prospect
Further Information
Received
21 April 2005
Publication Date:
12 October 2005 (online)
Publication History
Publication Date:
12 October 2005 (online)
Abstract
N,N′-Diarylureas having electron-donating substituents at appropriate positions react with phosphorus(III) bromide forming the new heterocyclic system 2,4,1-benzodiazaphosphinan-3-one. N-(5-Pyrazolyl), N′-arylureas, and N,O-diarylcarbamates also undergo an analogous heterocyclization affording 1H-pyrazolo[4,3-c][1,5,2]diazaphosphinan-3-one and 2,4,1-benzoxazaphosphinan-3-one ring systems.
Key words
N,N′-diarylureas - N-(5-pyrazolyl) - N′-arylureas - N,O-diarylcarbamates - phosphorus(III) halides - phosphorylation - heterocyclization
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