[inline-graphic not available: see fulltext] 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 α-hydroxy or α-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.