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Synthesis of 4-oxo-6-styryl-4H-pyran-2-carbonitriles and their application for the construction of new 4-pyrone derivatives

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Abstract

Synthesis of 2-cyano-6-styryl-4-pyrones has been developed on the basis of 6-metylcomanic acid via modifications of the methyl and carboxyl groups. Reactions of these pyrones with nucleophiles proceeded as an attack at the cyano group, whereas 1,3-dipolar cycloaddition of stabilized azomethine ylides occurred at the styryl moiety stereo- and regioselectively. The effective approach based on the side chain manipulation of the 2-cyano-6-styryl-4-pyrones led to 2-azolyl-6-styryl-4-pyrones and 4-pyrone conjugates with the pyrrolidine moiety. Reactivity of the prepared 2-cyano-6-styryl-4-pyrones was estimated with the use of quantum chemical calculations, and the observed chemoselectivity was explained by charge and orbital controls. The photophysical properties of the cyanopyrones were determined in view of further application as simple molecular fluorophores with large Stokes shifts.

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Acknowledgments

Analytical studies were carried out using equipment at the Center for Joint Use ‘Spectroscopy and Analysis of Organic Compounds’ at the Postovsky Institute of Organic Synthesis of the Russian Academy of Sciences (Ural Branch) and the Laboratory of Complex Investigations and Expert Evaluation of Organic Materials of the Center for Joint Use at the Ural Federal University.

Funding

This work was financially supported by the Russian Science Foundation (Grant 18-13-00186, https://rscf.ru/project/18-13-00186/).

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Authors and Affiliations

  1. Institute of Natural Sciences and Mathematics, Ural Federal University, 51 Lenina Ave., Ekaterinburg, Russian Federation, 620000

    Dmitrii L. Obydennov, Alena E. Simbirtseva & Vyacheslav Y. Sosnovskikh

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  1. Dmitrii L. Obydennov
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  2. Alena E. Simbirtseva
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  3. Vyacheslav Y. Sosnovskikh
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Correspondence to Dmitrii L. Obydennov.

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Obydennov, D.L., Simbirtseva, A.E. & Sosnovskikh, V.Y. Synthesis of 4-oxo-6-styryl-4H-pyran-2-carbonitriles and their application for the construction of new 4-pyrone derivatives. Res Chem Intermed 48, 2155–2179 (2022). https://doi.org/10.1007/s11164-022-04694-w

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