A convenient synthesis of functionalized pyrazolones bearing a highly twisted 1,3-butadiene moiety with skew geometry

Abstract

The four-component reaction among arylhydrazine, alkyl acetoacetate derivatives, alkyl isocyanides, and dialkyl acetylenedicarboxylates, leading to the formation of dialkyl 2-[(Z)-(alkylamino)(3-alkyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)methyl] fumarates is described. The structure of target compounds was confirmed using X-ray diffraction study. These pyrazolone derivatives contain a highly twisted exocyclic 1,3-butadiene moiety with skew (ϕ = 87°) geometry.

Graphical Abstract

Keywords:

• Pyrazolone
• isocyanides
• polarized double bond
• acetylenic esters
• restricted rotation