Synthesis of Functionalized 4<i>H</i>-Pyran and Cyclohexanone Derivatives via Three-Component Reactions of Dimethyl Acetonedicarboxylate, Aromatic Aldehydes, and Malononitrile

Abstract

Dependent on the reaction time, the three-component condensation of dimethyl acetonedicarboxylate (1), aromatic aldehydes 2, and malononitrile (3) gives rise to 4H-pyran derivatives 5 after reflux for 15 min. Moreover, using excess of benzaldehyde and prolonged heating for 150 min afforded multifunctional cyclohexanone derivatives 8. Different substitution patterns in the phenyl nucleus of 8 can be achieved by condensation of 4H-pyran derivatives 5 with benzaldehydes 2.