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Chemistry of Heterocyclic Compounds

, Volume 53, Issue 12, pp 1310–1314 | Cite as

Synthesis of symmetrical chromeno[2,3-b]chromenes on the basis of о-quinone methides and 1,1-bis(morpholino)ethene

  • Vitaly A. OsyaninEmail author
  • Dmitry V. Osipov
  • Maxim R. Demidov
  • Pavel E. Krasnikov
  • Yuri N. Klimochkin
Article
  • 112 Downloads

The reaction of 1,1-bis(morpholino)ethene with precursors of о-quinone methides derived from Mannich bases of phenols and 2-naphthols provided a series of chromeno[2,3-b]chromenes. The cascade process included a hetero-Diels–Alder reaction between о-quinone methide and ketenaminal, elimination of secondary amine, and [4+2] cycloaddition between о-quinone methide and the chromene intermediate.

Keywords

chromeno[2,3-b]chromenes ketenaminals о-quinone methides cascade reactions Diels–Alder reaction 

Notes

This work received financial support from the Ministry of Education and Science of the Russian Federation (contract 02.a03.21.0008), the Russian Foundation for Basic Research, and the Samara Regional Government within the framework of the scientific project 17-43-630838 r_a.

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Copyright information

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

Authors and Affiliations

  • Vitaly A. Osyanin
    • 1
    • 2
    Email author
  • Dmitry V. Osipov
    • 1
  • Maxim R. Demidov
    • 1
  • Pavel E. Krasnikov
    • 1
  • Yuri N. Klimochkin
    • 1
  1. 1.Samara State Technical UniversitySamaraRussia
  2. 2.RUDN UniversityMoscowRussia

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