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Reactions of Quinolinecarbaldehydes with Arenes under Superelectrophilic Activation. NMR and DFT Studies of Dicationic Electrophilic Species

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Chemistry of Heterocyclic Compounds Aims and scope

N,O-Diprotonated forms (dications) of various quinolinecarbaldehydes were theoretically studied by DFT calculations. It was found that the most reactive electrophilic dications are expected to be generated from 2- and 4-quinolinecarbaldehydes compared to the other quinolinecarbaldehydes. Experimental studies of protonation of quinoline-2(6,8)-carbaldehydes in Brønsted acids (CF3SO3H, H2SO4) by means of 1H, 13C, and 15N NMR revealed the formation of the corresponding N-protonated O-protosolvated species. Reactions of quinoline-2(6,8)-carbaldehydes with arenes in the presence of Brønsted (TfOH) and Lewis acids (AlX3, X = Cl, Br) or acidic zeolites led to the formation of the corresponding 2(6,8)-(diarylmethyl)quinolines. However, 6- and 8-quinolinecarbaldehydes gave additionally unusual products – 6(8)-(arylmethyl)quinolines.

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Authors and Affiliations

  1. Saint Petersburg State Forest Technical University, 5 Institutskiy Pereulok, Saint Petersburg, 194021, Russia

    Marina А. Borisova, Dmitry S. Ryabukhin & Aleksander V. Vasilyev

  2. All-Russia Research Institute for Food Additives, Branch of V. M. Gorbatov Federal Research Center for Food Systems of Russian Academy of Sciences, 55 Liteyny Ave, Saint Petersburg, 191014, Russia

    Dmitry S. Ryabukhin

  3. Center for Magnetic Resonance, Research Park, Saint Petersburg State University, 26 Universitetskiy Ave, Saint Petersburg, 198504, Russia

    Alexander Yu. Ivanov

  4. Institute of Chemistry, Saint Petersburg State University, 7/9 University Embankment, Saint Petersburg, 199034, Russia

    Irina A. Boyarskaya & Aleksander V. Vasilyev

  5. Research center for X-Ray Diffraction Studies, Research Park, Saint Petersburg State University, 26 Universitetskiy Ave, Saint Petersburg, 198504, Russia

    Dar’ya V. Spiridonova

  6. L. M. Litvinenko Institute of Physical-Organic Chemistry and Coal Chemistry, 50 Kharkivske Shose, Kyiv, 02160, Ukraine

    Mikhail O. Kompanets

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  1. Marina А. Borisova
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  7. Aleksander V. Vasilyev
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Correspondence to Aleksander V. Vasilyev.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(10), 1007–1016

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Borisova, M.А., Ryabukhin, D.S., Ivanov, A.Y. et al. Reactions of Quinolinecarbaldehydes with Arenes under Superelectrophilic Activation. NMR and DFT Studies of Dicationic Electrophilic Species. Chem Heterocycl Comp 57, 1007–1016 (2021). https://doi.org/10.1007/s10593-021-03015-0

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