P₂O₅-Hexamethyldisiloxane (HMDS): An Efficient System to Induce the Three-Component Reaction of Enolic Systems, Aromatic Aldehydes, and Acetonitrile

Abstract

Three-component reaction of an enolizable compound, such as acetophenone, methyl acetoacetate, 4-hydroxycoumarin, 2-naphthol, or 3-hydroxy-2-naphthoic acid; an aromatic aldehyde, and acetonitrile induced by phosphorus pentoxide and hexamethyldisiloxane leads to 2-acetylamino ketones, methyl 3-(acetylamino aryl methyl)-3-oxobutanoates, 3-(acetylamino aryl methyl)-4-hydroxycoumarins, 1-(acetylamino aryl methyl)-2-naphthols, or 4-(acetylamino aryl methyl)-3-hydroxy-2-naphthoic acids in excellent yields.

Keywords:

• Aryl aldehydes
• hexamethyldisiloxane
• 4-hydroxycoumarin
• 2-naphthol
• phosphorus pentoxide
• three-component reaction

Notes

^a Isolated yields.

^a Yields refer to the pure isolated products. Compounds 7a–i were new, and their structures were deducted by elemental and spectral analysis. Compounds 7j–s were known compounds, and their structures were deduced by comparing their melting points and spectral data with authentic samples.^{[ 17 ]}