One-pot synthesis of functionalized spirobenzofuranones via MCR involving 3-cyanochromones
Zarganes-Tzitzikas T., Terzidis MA., Stephanidou-Stephanatou J., Tsoleridis CA., Kostakis GE.
Another aspect concerning chromone chemistry leading to the one-pot synthesis of functionalized novel spirobenzofuranones has been described. The synthesis involves reaction of the zwitterionic intermediates formed by the 1:1 interaction between isocyanides and acetylenecarboxylates with 3-cyanochromones, whereupon through an unexpected and unprecedented reaction of the chromone moiety the isolated benzofuranones are formed. The regioselectivity of the reaction was investigated by DFT calculations. The geometries of the intermediates, transition structures, and intermediate products, leading to the final products, were optimized using the B3LYP functional with the 6-31G(d) basis set. The structures of the products were elucidated by 1D and 2D NMR experiments. Full assignment of all 1H and 13C NMR chemical shifts has been achieved. A plausible mechanistic rationale is proposed. © 2011 American Chemical Society.