Reactions of naphthalen-2-ol Mannich bases with β-aminoacrylonitriles and methyl 3-morpholinoacrylate

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.

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Acknowledgment

This study was supported by the Russian Foundation for Basic Research (project 18-33-20249). The authors are grateful to V. B. Rybakov (Moscow State University) for performing X-ray structural analysis.

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Correspondence to Vitaly А. Osyanin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(5), 529–536

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Lukashenko, A.V., Osipov, D.V., Osyanin, V.А. et al. Reactions of naphthalen-2-ol Mannich bases with β-aminoacrylonitriles and methyl 3-morpholinoacrylate. Chem Heterocycl Comp 56, 529–536 (2020). https://doi.org/10.1007/s10593-020-02695-4

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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