Efficient and Green Method for the Synthesis of Highly Substituted Cyclohexadiene Derivatives in Aqueous Media

Abstract

Three-component reaction of aromatic aldehyde, malononitrile, and 2-(1-(3-chlorophenyl)propylidene)malononitrile in aqueous media catalyzed by tetraethylbenzylammonium chloride (TEBAC) at 90 °C gave 2-amino-6-(3-chlorophenyl)-5-methyl-4-arylcyclohexa-1,5-diene-1,3,3-tricarbonitrile derivatives. The structure of 4e was further confirmed by x-ray diffraction. This three-component reaction had the advantages of green solvent, good yield, and operational simplicity.

Keywords:

• Aqueous media
• cyclohexadiene
• malononitrile
• TEBAC

ACKNOWLEDGMENTS

We are grateful to the National Natural Science Foundation of China (20802061), the Natural Science Foundation (08KJD150019), and Qing Lan Project (08QLT001) of Jiangsu Education Committee for financial support.

Notes

^a Reagents and conditions: 1 (0.370 g, 2 mmol), malononitrile 2 (0.145 g, 2.2 mmol), 3 (0.432 g, 2 mmol), TEBAC (0.091 g, 0.2 mmol), H₂O (10 mL).

^b Isolated yields.

^a Reagents and conditions: 1 (2 mmol), malononitrile 2 (0.145 g, 2.2 mmol), 3 (0.432 g, 2 mmol), TEBAC (0.091 g, 0.2 mmol), and H₂O (10 mL).

^b Isolated yields.