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Issue 42, 2016
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Base mediated 1,3-dipolar cycloaddition of α-substituted vinyl phosphonates with diazo compounds for synthesis of 3-pyrazolylphosphonates and 5-pyrazolcarboxylates

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Abstract

5-Aryl-substituted pyrazol-3-ylphosphonates have been conveniently synthesized by 1,3-dipolar cycloaddition of 1-formamidovinylphosphonates and aryldiazomethanes under K2CO3/MeOH conditions at room temperature. These pyrazoles are formed in one pot via spontaneous elimination of formamide. Basic conditions prevent competitive formation of cyclopropylphosphonates. 3-Aryl substituted pyrazol-5-carboxylates can be synthesized by the same methodology from 1-arylvinylphosphonates and ethyl diazoacetate, although a stronger base NaH is necessary to ensure the success of the aromatization stage with the elimination of the diethoxylphosphoryl moiety.

Graphical abstract: Base mediated 1,3-dipolar cycloaddition of α-substituted vinyl phosphonates with diazo compounds for synthesis of 3-pyrazolylphosphonates and 5-pyrazolcarboxylates

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Publication details

The article was received on 16 Aug 2016, accepted on 22 Sep 2016 and first published on 26 Sep 2016


Article type: Paper
DOI: 10.1039/C6OB01780K
Citation: Org. Biomol. Chem., 2016,14, 10000-10010
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    Base mediated 1,3-dipolar cycloaddition of α-substituted vinyl phosphonates with diazo compounds for synthesis of 3-pyrazolylphosphonates and 5-pyrazolcarboxylates

    N. S. Goulioukina, N. N. Makukhin, E. D. Shinkarev, Y. K. Grishin, V. A. Roznyatovsky and I. P. Beletskaya, Org. Biomol. Chem., 2016, 14, 10000
    DOI: 10.1039/C6OB01780K

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