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Synthesis of fused heterocyclic systems via the Mallory photoreaction of arylthienylethenes

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Abstract

Photochemical oxidative cyclization of 2- and 3-thienylstilbenes (heterostilbenes) containing mono-, di- and trimethoxy groups in the benzene ring or heterocyclic fragment results in the formation of isomeric thieno-annelated polycyclic aromatic compounds demonstrating optical properties that differ from those of initial stilbene derivatives. The structures of cyclic products were evaluated via 1H and 13C NMR, HRMS, elemental analysis and X-ray crystallography. The research was aimed to study the effect of substituents in stilbene derivatives of thiophene as well as the position of the styryl fragment in the thiophene nucleus on the occurrence of photocyclization reactions.

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Authors and Affiliations

  1. Department of Chemistry, Lomonosov Moscow State University, 119992, Leninskie Gory, Moscow, Russia

    Natalia V. Dyachenko, Andrey V. Khoroshutin, Yulia A. Sotnikova, Sergey D. Tokarev, Alexander V. Anisimov & Olga A. Fedorova

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova str., 119991, Moscow, Russia

    Natalia V. Dyachenko, Valentina A. Karnoukhova, Sergey D. Tokarev, Yurii V. Fedorov & Olga A. Fedorova

Authors
  1. Natalia V. Dyachenko
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  2. Andrey V. Khoroshutin
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  3. Yulia A. Sotnikova
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  4. Valentina A. Karnoukhova
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  5. Sergey D. Tokarev
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  6. Alexander V. Anisimov
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  7. Yurii V. Fedorov
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  8. Olga A. Fedorova
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Corresponding author

Correspondence to Olga A. Fedorova.

Additional information

Electronic supplementary information (ESI) available. CCDC 1903023–1903031. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c9pp00289h

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Dyachenko, N.V., Khoroshutin, A.V., Sotnikova, Y.A. et al. Synthesis of fused heterocyclic systems via the Mallory photoreaction of arylthienylethenes. Photochem Photobiol Sci 18, 2901–2911 (2019). https://doi.org/10.1039/c9pp00289h

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  • DOI: https://doi.org/10.1039/c9pp00289h

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