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Synthesis 2005(18): 3124-3134  
DOI: 10.1055/s-2005-916029
PAPER
© Georg Thieme Verlag Stuttgart · New York

Phosphorylation of Arylureas and Arylcarbamates: A New Prospect

Dmitriy M. Volochnyuk*a, Alexei O. Pushechnikova, Dmitriy G. Krotkoa, Alexandr M. Pinchuka, Andrei A. Tolmachevb
a Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanskaya 5, Kyiv-94, Kiev 02094, Ukraine
b Research and Development Center for Chemistry and Biology, National Taras Shevchenko University, 62 Volodymyrska st., Kyiv-33, Kiev 01033, Ukraine
Fax: +38(44)5373253; e-Mail: D.Volochnyuk@enamine.net;
Further Information

Publication History

Received 21 April 2005
Publication Date:
12 October 2005 (online)

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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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