Synthesis of New 2-(4-(1,4-Dihydropyridin-4-yl)Phenoxy)-N-Arylacetamides and Their Heterocyclic-Fused Derivatives via Hantzsch-Like Reaction

Abstract

A simple and effective approach has been established for the synthesis of a new series of 1,4-dihydropyridin-3,5-dicarbonitriles, hexahydroacridine-1,8-diones, 7,14-dihydro-6H,8H-dichromeno[4,3-b:3′,4′-e]pyridine-6,8-diones, and 1,4,7,8-tetrahydrodipyrazolo[3,4-b:4′,3′-e]pyridines which are linked to phenoxy-N-arylacetamide. The novel products were obtained through the Hantzsch reaction of various 2-(4-formylphenoxy)-N-arylacetamides with the respective 3-aminocrotononitrile or a mixture of 1,3-dicarbonyl compounds and ammonium acetate. Elemental and spectral data were used to confirm the structures of the newly synthesized compounds. The desired products could not be made by alkylation of the suitable phenol derivatives with 2-chloro-N-phenylacetamide.

Keywords:

• 2-(4-Formylphenoxy)-N-arylacetamides
• active methylene reagents
• Hantzsch reaction
• 1,4-dihydropyridines
• fused-dihydropyridines