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

Антон В. Лукашенко, Дмитрий В. Осипов, Виталий А. Осянин, Юрий Н. Климочкин
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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.

Keywords


2,3-dihydro-1H-benzo[f]chromene; 1,4-dihydropyridine; naphthalen-2-ol; 1,2-naphthoquinone 1-methide; push-pull olefin; Diels–Alder reaction.

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