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Synthesis 2003(6): 0906-0914
DOI: 10.1055/s-2003-38685
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Synthesis of (5-Aminopyrazol-4-yl)-phosphonic Acid Derivatives from 1-Aryl-5-arylcarboxamidopyrazoles through Pyrazolo[4,3-c][1,5,2]-oxazaphosphinines

Dmitriy M. Volochnyuk*a, Alexei O. Pushechnikova, Dmitriy G. Krotkoa, Georgiy N. Koydana, Anatoliy P. Marchenkoa, Alexander N. Chernegaa, Alexander M. Pinchuka, Andrei A. Tolmachevb
a Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanskaya 5, Kyiv-94, 02094, Ukraine
Fax: +380(44)2696794; e-Mail: dov@fosfor.kiev.ua ;
b Research and Development Center for Chemistry and Biology, National Taras Shevchenko University, 62 Volodymyrska st., Kyiv-33, 01033, Ukraine
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Publikationsverlauf

Received 6 February 2003
Publikationsdatum:
16. April 2003 (online)

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Abstract

1-Aryl-5-arylcarboxamidopyrazoles react with phos­phorus(III) halides giving the new heterocyclic system: pyrazolo[4,3-c][1,5,2]oxazaphosphinine. Treatment of pyrazolo[4,3-c][1,5,2]oxazaphosphinines with nucleophilic or electrophilic reagents leads to a cleavage of the oxazaphosphinine ring yielding derivatives of (5-aminopyrazol-4-yl)phosphonic acid.

Key words

1-aryl-5-arylcarboxamidopyrazoles - phosphorus(III) halides - phosphorylation - heterocyclization - ring opening