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Directed synthesis of new spiro-fused photochromes of diarylethene series

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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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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Authors and Affiliations

  1. Chuvash State University named after I. N. Ulyanov, Moskovskiy Ave. 15, Cheboksary, 428015, Russia

    Mikhail Yu. Belikov, Mikhail Yu. Ievlev, Irina V. Belikova & Oleg V. Ershov

  2. M. V. Lomonosov Moscow State University, Leninskie Gory 1, Bldg. 3, Moscow, 119991, Russia

    Viktor A. Tafeenko

  3. N. S. Kurnakov Institute of General and Inorganic Chemistry, Leninskiy Ave. 31, Moscow, 119991, Russia

    Marina D. Surazhskaya

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  1. Mikhail Yu. Belikov
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  2. Mikhail Yu. Ievlev
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  3. Irina V. Belikova
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  4. Oleg V. Ershov
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  5. Viktor A. Tafeenko
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  6. Marina D. Surazhskaya
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Correspondence to Mikhail Yu. Belikov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(6), 518–525

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Belikov, M.Y., Ievlev, M.Y., Belikova, I.V. et al. Directed synthesis of new spiro-fused photochromes of diarylethene series. Chem Heterocycl Comp 51, 518–525 (2015). https://doi.org/10.1007/s10593-015-1731-4

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