Synthesis of functionalized furan using multicomponent reaction of isatin

Protonation of the highly reactive 1:1 intermediates produced in the reaction between alkyl(aryl) isocyanides and dibenzoylacetylene by isatin, leads to vinylnitrilium cations, which undergo carbon-centered Michael type addition with the conjugate base of the NH-acid to produce highly functionalized 1-(3-furyl)-1H-indole-2,3-diones. A dynamic NMR effect is observed in the 1H NMR spectra of these compounds as a result of restricted rotation around the single bond linking the indole moiety and the furan system. The free-energy of activation (ΔG#) for this process is 69-71 kJ mol-1.