Synthesis And Regioselectivity Synthesis Of Aminophosphonic Acid Derivatives By Three-component Domino Reaction

The progress of one-pot synthesis of α-aminophosphonates via the Kabachnik-Fieldsreaction remains in water, regional and stereoscopic selective synthesis of novelspirooxindole-fused heterocycles derivatives are reviewed in this paper. Based on highefficiency and selectivity of multicomponent reaction, we report now on the construction ofthis unique trans-spirooxindole-fused phosphorous heterocycles in good yields withexcellent regioselectivity under the catalyst-free conditions by a three-component dominoreaction. We report on an ecofriendly, facile, and efficient methodology for the synthesis ofα-amino phosphonates by a three-component Kabachnik-Fields reaction system in an aqueousmedium.1. The three-component Kabachnik–Fields reaction of substituted salicylaldehydes,aromatic amine, and triphenyl phosphite in water was effectively catalyzed byp-toluenesulfonic acid to give various α-amino phosphonates in good yields(80%~93.8%).The catalyst is easily available and inexpensive, and the process is green and mild. Theproduct structures were characterized by IR,1H NMR,13C NMR,31P NMR and elementanalyes. The effect of different reaction conditions on yield and the proposed mechanism ofthe cascade reaction had been investigated.2. A highly efficient, catalyst-free and regioselective synthesis of structurally diversespirooxindole-fused phosphorous heterocycles derivatives was constructed in goodyields(80%~95%) by means of a three-component domino reaction of isatins,phenyldichloro phosphine or phenyl phosphorodichloridite and o-aminophenol in THF reflux.The product structures were characterized by IR,1H NMR,13C NMR,31P NMR and massspectrum. The effect of different reaction conditions on yield and the proposed mechanism ofthe cascade reaction had been investigated.3. In order to further confirm the configuration of the isolated product9a, the compound9a was recrystallized, obtained as stable, white crystals and determined by X-ray diffractionanalysis. it was found that products9a are the racemic mixture of two enantiomers(2SP,3RCand2RP,3SC) with trans-geometric configuration4. The values of antimicrobial activities of the title compound are listed in Table3.5.These spirooxindole-fused phosphorous heterocycles are promising candidates for drugdiscovery.