A. Gutnov, V. Abaev, O. Demidov
Apr 11, 2019
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Chemistry of Heterocyclic Compounds
Abstract
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.