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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

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Chemistry of Heterocyclic Compounds Aims and scope

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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Acknowledgement

This work was supported by the Russian Foundation for Basic Research (grant 18-33-20249).

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Authors and Affiliations

  1. Samara State Technical University, 244 Molodogvardeyskaya St., Samara, 443100, Russia

    Anton V. Lukashenko, Dmitry V. Osipov, Vitaly А. Osyanin & Yuri N. Klimochkin

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  1. Anton V. Lukashenko
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  2. Dmitry V. Osipov
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  3. Vitaly А. Osyanin
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  4. Yuri N. Klimochkin
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Correspondence to Vitaly А. Osyanin.

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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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