Synthesis of a novel tetracationic acidic organic salt based on DABCO and its applications as catalyst in the Knoevenagel condensation reactions in water

Abstract

Synthesis of a novel tetracationic acidic organic salt based on DABCO containing two sulfonic acid groups in the skeleton and four hydrogensulfate groups as counterion is described. Its catalytic efficiency in the Knoevenagel condensation of aldehydes with active cyclic methylene compounds in water is investigated. While 2,2'-(phenylmethylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) derivatives were obtained in 40-98% isolated yields in the reaction of aldehydes with dimedone, the corresponding Knoevenagel adducts were provided in 85-95% yields using 1,3-dimethylbarbituric acid. In addition, a DABCO-based polycationic organic salt polymer was prepared and characterized for the first time.

Graphical Abstract

Keywords:

• DABCO
• DABCO-based polymer
• dimedone
• 1,3-dimethylbarbituric acid
• Knoevenagel condensation
• tetracationic acidic organic salt
• tetraketone

Additional information

Funding

We thank the research council of Kharazmi University for supporting this work.