1,1,3,3- N, N, N', N'-Tetramethylguanidinium trifluoroacetate as an ionic liquid, efficiently promotes one-pot, three-component condensation of aldehydes, alkyl nitriles and alpha-hydroxy or alpha-amino activated C-H acid to afford the corresponding pyran annulated heterocyclic systems. Ionic liquid can be recycled for subsequent reactions without any appreciable loss of efficiency.