1,3-Dipolar cycloaddition of N-[4-nitrophenyl]-C-[2-furyl] nitrilimine with some dipolarophiles: A combined experimental and theoretical study

Reaction of vinyl acetate (3), 2-propyne-1-ol (4) and styrene (5) as dipolarphiles with N-[4-nitrophenyl]-C-[2-furyl] nitrilimine which was generated in situ has been shown to afford 3-(furan-2-yl)-1-(4-nitrophenyl)-4,5-dihydro-1H-pyrazol-5-yl acetate (6), (3-(furan-2-yl)-1-(4-nitrophenyl)-1H-pyrazol-5-yl)methanol (8) and 3-(furan-2-yl)-1-(4-nitrophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole (10). Reactivity and regiochemistry of these reactions were investigated using DFT-based reactivity indexes.