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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 10, pp 940–945 | Cite as

Reaction of cross-conjugated push-pull enamino ketones with 1,2-naphthoquinone 1-methides: synthesis of 3-aryl-1-(1H-benzo[f]chromen-2-yl)prop-2-en-1-ones

  • Kirill S. Korzhenko
  • Dmitry V. Osipov
  • Vitaly A. OsyaninEmail author
  • Pavel E. Krasnikov
  • Yuri N. Klimochkin
Article
  • 39 Downloads

A series of 3-aryl-1-(1H-benzo[f]chromen-2-yl)prop-2-en-1-ones, both unsubstituted and containing an aryl substituent at the C-1 position was obtained via the reaction of cross-conjugated push-push enamino ketones with 2-naphthol-derived Mannich bases. The cascade process involves the hetero-Diels–Alder reaction between 1,2-naphthoquinone 1-methide formed in situ and an enaminone, followed by the elimination of a dimethylamine molecule.

Keywords

1H-benzo[f]chromenes enamino ketones Mannich bases о-quinone methides cascade reactions Diels–Alder reaction 

Notes

This work was supported by the Russian Foundation for Basic Research in the framework of the project № 17-03-01158.

Supplementary material

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ESM 1 (PDF 2169 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Kirill S. Korzhenko
    • 1
  • Dmitry V. Osipov
    • 1
  • Vitaly A. Osyanin
    • 1
    Email author
  • Pavel E. Krasnikov
    • 1
  • Yuri N. Klimochkin
    • 1
  1. 1.Samara State Technical UniversitySamaraRussia

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