۱,۳-Disulfonic Acid Imidazolium Trifluoroacetate as a Highly Efficient and Dual-Functional Catalyst for the Pseudo Five-Component Reaction of Phenylhydrazine with Ethyl Acetoacetate and Arylaldehydes

Ionic liquid ۱,۳-disulfonic acid imidazolium trifluoroacetate ([Dsim][TFA]) has been exploited as a highly efficient catalyst for the one-pot pseudo five-component reaction of phenylhydrazine (۲ eq.) with ethyl acetoacetate (۲ eq.) and arylaldehydes (۱ eq.) in ethanol (reflux conditions). In this reaction, ۴,۴′‐(arylmethylene)‐bis(۳‐methyl‐۱‐phenyl‐۱H‐ pyrazol‐۵‐ol)s have been obtained in high yields and relatively short reaction times. High efficacy of [Dsim][TFA] can attributed to dual-functionality (possessing three acidic and one basic sites). A plausible and attractive mechanism based on dual-functionality of the catalyst has been proposed.

Keywords:

Phenylhydrazine , Ethyl acetoacetate , Arylaldehyde , ۴ , ۴′‐(Arylmethylene)‐bis(۳‐methyl‐۱‐phenyl‐۱H‐pyrazol‐۵‐ol) , ۱ , ۳-Disulfonic acid imidazolium trifluoroacetate ([Dsim][TFA]) , Multi-component reaction