Phosphorylation of Arylureas and Arylcarbamates: A New Prospect

Dmitriy M. Volochnyuk; Alexei O. Pushechnikov; Dmitriy G. Krotko; Alexandr M. Pinchuk; Andrei A. Tolmachev

doi:10.1055/s-2005-916029

PAPER

Phosphorylation of Arylureas and Arylcarbamates: A New Prospect

Dmitriy M. Volochnyuk*^a, Alexei O. Pushechnikov^a, Dmitriy G. Krotko^a, Alexandr M. Pinchuk^a, Andrei A. Tolmachev^b
^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;

Abstract

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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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