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.

Graphical Abstract

Keywords:

• Dicyanoanillines
• malononitril
• multi-component reactions
• organocatalysis
• pseudo-five-component

Additional information

Funding

The Research Council at CCERCI [Grant # 96-110] is acknowledged for financial support of this work.