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Chemistry of Heterocyclic Compounds

, Volume 51, Issue 6, pp 518–525 | Cite as

Directed synthesis of new spiro-fused photochromes of diarylethene series

  • Mikhail Yu. Belikov
  • Mikhail Yu. Ievlev
  • Irina V. Belikova
  • Oleg V. Ershov
  • Viktor A. Tafeenko
  • Marina D. Surazhskaya
Article

The reaction of tetracyanoethylated 1,2-diarylethanones with morpholine was used for directed synthesis of spiro-fused diarylethenes, 8-amino-1-imino(oxo)-6-morpholino-2-oxa-7-azaspiro[4.4]nona-3,6,8-triene-9-carbonitriles. The intermediates in this process were tetracyanoalkanone salts. The formation of spiranes was sensitive to the nature of aromatic substituents at the carbonyl group of 3,4-diaryl-4-oxobutane-1,1,2,2-tetracarbonitriles. The obtained spiro-fused diarylethenes exhibited photochromic properties.

Keywords

1,2-diarylethanones diarylethenes tetracyanoethylene ethene linker non-bonded strain photochromes spiro compounds spirofusion tetracyanoethylation 

Notes

This work received financial support from the Grants Council of the President of Russian Federation (grant MK-97.2014.3).

X-ray structural investigation of salt 3c was performed by using equipment obtained with financial support from the Development Program of the Moscow University and within the framework of Cooperation Agreement between the Department of Chemistry of M. V. Lomonosov Moscow State University and the Chemistry and Pharmacy Department of Chuvashia State University named after I. N. Ulyanov.

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Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Mikhail Yu. Belikov
    • 1
  • Mikhail Yu. Ievlev
    • 1
  • Irina V. Belikova
    • 1
  • Oleg V. Ershov
    • 1
  • Viktor A. Tafeenko
    • 2
  • Marina D. Surazhskaya
    • 3
  1. 1.Chuvash State University named after I. N. UlyanovCheboksaryRussia
  2. 2.M. V. Lomonosov Moscow State UniversityMoscowRussia
  3. 3.N. S. Kurnakov Institute of General and Inorganic ChemistryMoscowRussia

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