A kind of synthetic method of chiral phosphorus-containing pyrazolone compound

Abstract

The invention discloses a method for synthesizing chiral phosphorus-containing pyrazolone compounds. Specifically, pyrazolidinone imine and diaryl phosphorus oxide or dimethyl phosphite are used as reactants, and the chiral multifunctional chiral The product was synthesized in a solvent under the catalysis of a neutral square amide. The method disclosed by the invention has simple and easy raw materials, mild reaction conditions, simple and convenient post-treatment, wide range of applicable substrates, high yield and high enantioselectivity; the product synthesized thereby can be used to synthesize drugs and insecticides intermediates.

Description

technical field [0001] The invention relates to the synthesis of aminophosphorus compounds, in particular to a catalytic synthesis method of chiral pyrazolidinone-type aminophosphorus compounds. Background technique [0002] α-Aminophosphonic acid compounds have a wide range of biological activities such as anti-tumor, anti-plant virus, plant growth regulation, weed control, bactericidal, enzyme activity inhibition, anti-oxidation and radiation protection, and destruction of biological cell membranes, and have attracted the attention of many scientists. Chiral pyrazolidinone aminophosphorus compounds, as α-phosphoramidate derivatives, also have similar potential application value, so choosing an efficient method to synthesize chiral pyrazolidinone aminophosphorus compounds has attracted the great attention of many chemists. There is great interest, and many synthetic methods have recently emerged. [0003] In the field of organic synthesis, the reaction catalyzed by asymmet...

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Problems solved by technology

[0005]JonC.Antilla et al. selected chiral magnesium phosphate reagents to catalyze imines and diphenylphosphoryloxygen for hydrogen phosphorylation to synthesize chiral aminophosphoryloxy compounds , the enantioselectivity of this process is moderate to high, there is no universal adaptability, and the catalyst is complex and difficult to synthesize (see: Ingle, G.K.; Liang, Y.; Mormino, M.G.; Li, G.; Fronczek, F.R.; Antilla, J.C., Org.Lett.2011, 13(8), 2054-2057.); Wang, W et al. selected chiral multifunctional thiourea catalyzed cyclic imine and dimethyl phosphite for hydrophosphorylation reaction Reaction synthesis of phosphoramidate compounds, the yield of this process is not very high and the enantioselectivity is medium to high, the substrate application range is not wide, and there is no general adaptability (see: Xie, H.; Song, A. ;Zhang,X.;Chen,X.;Li,H.;Sheng,C.;Wang,W.Chem.Commun.2013,49(9),928-930)

[0006] The prior art can synthesize chiral phosphoramidites, but has the disadvantages of low yield, complex catalyst and low selectivity, so it is necessary to find a new A method for synthesizing chiral pyrazolidinone aminophosphorus compounds, which not only has high yield and excellent enantioselectivity, but also requires mild reaction conditions and simple operation

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