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Synthesis of 2-aminochromene derivatives from 1-(2-imino-2H-chromen-3-yl)pyridin-1-ium perchlorates and nitromethane in basic medium

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Chemistry of Heterocyclic Compounds Aims and scope

Novel 2-amino-4-(nitromethylidene)chromenes were obtained as a result of the reaction of 1-(2-imino-2H-chromen-3-yl)pyridinium perchlorates and nitromethane by the action of DBU at reflux in trifluoroethanol. The starting 2-iminochromenes are readily accessible from the corresponding salicylic aldehydes and quaternary cyanomethyl pyridinium salts. The reaction is tolerant to substituents of different nature (alkyl, alkoxy, halogen); a limitation is the presence of strong electron-withdrawing substituents in the benzene ring of chromene. During the reaction, the products precipitate and can be isolated by filtration.

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The reported study was funded by the Russian Foundation for Basic Research within the framework of research project No. 18-302-00001.

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Authors and Affiliations

  1. RUDN University, 6 Miklukho-Maklaya St., Moscow, 117198, Russia

    Olga А. Storozhenko, Xiaoyi Yue, Alexey А. Festa, Alexey А. Varlamov & Leonid G. Voskressensky

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  1. Olga А. Storozhenko
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  2. Xiaoyi Yue
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  3. Alexey А. Festa
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  4. Alexey А. Varlamov
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  5. Leonid G. Voskressensky
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Correspondence to Olga А. Storozhenko.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(9), 1161–1166

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Storozhenko, O.А., Yue, X., Festa, A.А. et al. Synthesis of 2-aminochromene derivatives from 1-(2-imino-2H-chromen-3-yl)pyridin-1-ium perchlorates and nitromethane in basic medium. Chem Heterocycl Comp 56, 1161–1166 (2020). https://doi.org/10.1007/s10593-020-02793-3

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