A simple, highly efficient and green route for the synthesis of 2-amino-4H-benzo[b]pyrans and 1,4-dihydropyridines has been developed by using -cyclodextrin (-CD) as catalyst in deep eutectic solvent (DES) of urea-choline chloride (urea-ChCl), for the first time, accomplished via a one-pot, three-component strategy. All the reactions were successfully carried out under mild conditions and gave good to excellent yields (86-98%) in 8-28min in the presence of 5mol% of the -CD catalyst. The short reaction time, green reaction medium, moderate reaction conditions, simple work-up procedure and use of easily available reagents are the attractive features of this novel synthetic method. More importantly, the urea-ChCl--CD catalytic system was regenerated and reused up to 6 times with a slight drop in the product yields. [GRAPHICS] .