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Betti reaction of 2-naphthol, furfural, and acetamide: an unexpected case of secondary carbo-Piancatelli rearrangement

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Chemistry of Heterocyclic Compounds Aims and scope

Condensation of 2-naphthol, furfural, and acetamide in the presence of boric acid as acidic catalyst has led to Betti product N-[furan-2-yl(2-hydroxynaphthalen-1-yl)methyl]acetamide along with a new 10,10-dihydrocyclopenta[b]naphtho[1,2-d]furan derivative, which resulted from rare carbo-Piancatelli rearrangement. The structure is confirmed by 1H, 13C NMR, HRMS, and X-ray analyses. Mechanism of the transformation is discussed.

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Authors and Affiliations

  1. North Ossetian State University, 44-46 Vatutina St., Vladikavkaz, 362025, Russia

    Andrey V. Gutnov & Vladimir T. Abaev

  2. ChiroBlock GmbH, 1a Andresenstr., Wolfen, 06766, Germany

    Andrey V. Gutnov

  3. North Caucasus Federal University, 2a Kulakova St., Stavropol, 355029, Russia

    Oleg P. Demidov

Authors
  1. Andrey V. Gutnov
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  2. Vladimir T. Abaev
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  3. Oleg P. Demidov
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Correspondence to Andrey V. Gutnov.

Additional information

Supplementary information file containing 1H and 13C NMR spectra of both compounds, as well as results of X-ray crystallographic analysis of compound 2 is available at the journal website http://link.springer.com/journal/10593.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(3), 280–282

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Gutnov, A.V., Abaev, V.T. & Demidov, O.P. Betti reaction of 2-naphthol, furfural, and acetamide: an unexpected case of secondary carbo-Piancatelli rearrangement. Chem Heterocycl Comp 55, 280–282 (2019). https://doi.org/10.1007/s10593-019-02454-0

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  • DOI: https://doi.org/10.1007/s10593-019-02454-0

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