Pseudo-five-component organocatalyzed synthesis of dicyanoanillines using only malononitrile and aromatic aldehydes

Abstract

A pseudo-five-component reaction leading to efficient synthesis of dicyanoanillines was developed using only aromatic aldehydes and malononitrile as the starting reactants. Mechanistic studies suggested that a malononitrile dimer and the Knoevenagel condensation product of benzaldehyde, initially formed in the reaction mixture, combine with a fourth equivalent of malononitrile to form the final product. X-ray crystallography analysis of one of the derivatives confirmed the structure of the products.