REACTIONS OF NAPHTHALEN-2-OL MANNICH BASES WITH β-AMINOACRYLONITRILES AND METHYL 3-MORPHOLINOACRYLATE

Abstract

3-Amino-2,3-dihydro-1H-benzo[f]chromenes and 2-[(2-hydroxynaphthalen-1-yl)methyl]-2,3-dihydro-1H-benzo[f]chromene-2-carbonitriles were obtained via the reaction of naphthalen-2-ol Mannich bases with β-aminoacrylonitriles and methyl 3-morpholinoacrylate as products of [4+2] cycloaddition of push-pull olefins to the corresponding 1,2-naphthoquinone 1-methide. The reaction of 3-amino-3-phenylacrylonitrile with Mannich bases leads to the formation of 1,4-dihydropyridine-3,5-dicarbonitriles.