A series of 3-amino-1H-benzo[f]chromenes were obtained in the reaction of 1-[(dimethylamino)methyl]naphthalen-2-ol with push-pull ketene N,S-acetals containing an electron-withdrawing group in the α-position. It is assumed that the reaction proceeds as a [4+2] cycloaddition of ketene N,S-acetals to in situ generated 1,2-naphthoquinone 1-methide. Quantum-chemical methods were used to study the synchronicity of the Diels–Alder reaction.
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This work was supported by the Russian Foundation for Basic Research (grant 18-33-20249).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(5), 521–528
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Lukashenko, A.V., Osipov, D.V., Osyanin, V.А. et al. α-Functionalized ketene N,S-acetals as two-carbon synthons in the reaction with 1,2-naphthoquinone 1-methide. Synthesis of 3-amino-1H-benzo[f]chromenes. Chem Heterocycl Comp 56, 521–528 (2020). https://doi.org/10.1007/s10593-020-02694-5
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DOI: https://doi.org/10.1007/s10593-020-02694-5