Facile and Green Method for the Synthesis of β-Aminoketone Derivatives in Aqueous Media

Abstract

Three-component reaction of aromatic aldehyde, 2-naphthalenamine, and 1,2-diphenylethanone in aqueous media catalyzed by triethylbenzylammonium chloride (TEBAC) at 90 °C gave 3-aryl-3-(naphthalen-2-ylamino)-1,2-diphenylpropan-1-one derivatives. The enol form of 1,2-diphenylethanone was tentatively proposed to participate in the formation of the products. Compared with previous methods, this three-component reaction has the advantages of green solvent, good yields, and operational simplicity.

Keywords:

• Aqueous media
• 1,2-diphenylethanone
• 2-naphthalenamine
• TEBAC

ACKNOWLEDGMENTS

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

Notes

^a Reagents and conditions: 1 (0.302 g, 2 mmol), 2-naphthalenamine 2 (0.286 g, 2 mmol), 1,2-diphenylethanone 3 (0.392 g, 2 mmol), and TEBAC (0.091 g, 0.2 mmol), solvent (10 mL).

^b Isolated yields.

^a Reagents and conditions: 1 (2 mmol), 2-naphthalenamine 2 (0.286 g, 2 mmol), 1,2-diphenylethanone 3 (0.392 g, 2 mmol), TEBAC (0.091 g, 0.2 mmol), and solvent (10 mL).

^b Isolated yields.