An eco-friendly procedure for the efficient synthesis of arylidinemalononitriles and 4,4′-(arylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ols) in aqueous media

Abstract

Commercially available lithium hydroxide monohydrate (LiOH·H 2O) was found to be a novel "dual activation" catalyst for Knoevenagel condensation between malononitrile (1) or 3-methyl 1-phenyl-1H-pyrazol-5-(4H)-one (6) with aromatic aldehydes 2a-e leading to an efficient and easy synthesis of arylidenemalononitriles 3a-d and 4,4′-(arylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ols) 7a-c in short times. The reaction of aryl aldehydes with malononitrile afforded excellent yields after 1-6 min in aqueous media at room temperature. In case of 3-methyl-1-phenyl-1H-pyrazol-5-(4H)-one (6) and aromatic aldehydes afforded good yields after 60-75 min at 90°C. © 2012 Copyright Taylor and Francis Group, LLC.