Bagher Eftekhari-Sis

Compounds containing an cinnoline moiety have been shown to possess a broad range of biological activities, such as: anticancer, fungicidal, bactericidal, and anti-inflammatory properties.1 Therefore, the synthesis of cinnoline derivatives is of interest.2 In the recent years, the chemistryt of α-Ketoaldehydes and α-ketoesters in the synthesis of heterocyclic compounds has been attracted great attention.3-4 Also, the Baylis–Hillman (BH) adducts have been illustrated as suitable starting materials for the synthesis of variety of heterocyclic systems.5 Here we wish to report a novel three steps approach for the construction of dihydrochinnoline-5(6H)-ones starting from BH reaction of cyclohexenone with arylglyoxals to give corresponding BH adducts, which underwent acetylation using Ac2O in DCM in the presence of DMAP, followed by cyclocondensation with hydrazine hydrate in EtOH under air atmosphere and reflux condition.