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The flavanone pinostrobin in the synthesis of coumarin-chalcone hybrids with a triazole linker

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Chemistry of Heterocyclic Compounds Aims and scope

The reaction of flavanone pinostrobin with dibromoalkanes in acetone in the presence of potassium carbonate followed the path of retro-Michael addition – О-alkylation and resulted in the formation of the respective 2-(bromoalkoxy)chalcones. Treatment of the latter with sodium azide gave the respective azides, which were highly active in the Сu-catalyzed 1,3-dipolar cycloaddition reaction. The reaction of these azides with 6-substituted 7-ethynylcoumarins gave coumarin-chalcone hybrids containing a 1,2,3-triazole linker.

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This work received financial support from the Russian Science Foundation (grant No. 14-13-00822) and Partnering Program for Basic Research of the Siberian Branch of Russian Academy of Sciences and CIS Countries (project No. 108).

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Authors and Affiliations

  1. International Research and Production Holding “Phytochemistry”, 4 M. Gazaliyeva St., Karaganda, 100009, Kazakhstan

    Gulim K. Mukusheva, Pernesh Zh. Zhanymkhanova & Sergazy M. Adekenov

  2. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Lavrentieva Ave., Novosibirsk, 630090, Russia

    Alla V. Lipeeva, Elvira E. Shults, Yurii V. Gatilov & Makhmut M. Shakirov

  3. Novosibirsk State National Research University, 2 Pirogova St., Novosibirsk, 630090, Russia

    Elvira E. Shults & Yurii V. Gatilov

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  1. Gulim K. Mukusheva
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  2. Alla V. Lipeeva
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  3. Pernesh Zh. Zhanymkhanova
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  4. Elvira E. Shults
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  5. Yurii V. Gatilov
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  6. Makhmut M. Shakirov
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Correspondence to Elvira E. Shults.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(2), 146–152

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Mukusheva, G.K., Lipeeva, A.V., Zhanymkhanova, P.Z. et al. The flavanone pinostrobin in the synthesis of coumarin-chalcone hybrids with a triazole linker. Chem Heterocycl Comp 51, 146–152 (2015). https://doi.org/10.1007/s10593-015-1672-y

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  • DOI: https://doi.org/10.1007/s10593-015-1672-y

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