Triacylperhydro-1,3,5-triazines over Phenylsulfonic Acid Functionalized Mesoporous Silica

Abstract

An operationally simple, efficient, and environmentally benign synthesis of 1,3,5-triacylperhydro-1,3,5-triazines in good yields by reaction of different organic nitriles and trioxane in the presence of phenylsulfonic acid functionalized mesoporous silica under mild conditions was examined. The yields of the corresponding 1,3,5-trisubstituted perhydro-s-triazines synthesized from acetonitrile, propionitrile, butyronitrile, benzonitrile, and 1.3.5-trioxane were 95.7%, 96.1%, 84.2%, and 98.1%, respectively. The products were characterized by ¹H NMR, infrared, mass spectrometry, and elemental analysis. The mechanism of the formation of 1,3,5-triacylperhydro-1,3,5-triazines in acidic conditions was also described using a model reaction of butyronitrile with trioxane.

Keywords:

• Environmentally benign synthesis
• nitrile
• 1,3,5-triazines
• solid acid

ACKNOWLEDGMENT

Financial support from the Major State Basic Research Foundation Department of Equipment, China, is grateful acknowledged.

Notes

^a Isolated yields from solution.

^b The reaction is performed in the presence of a slight trace of water; the product is methyl bis-amides.

^c The yields of the starting materials recovered.