BETTI REACTION OF 2-NAPHTHOL, FURFURAL, AND ACETAMIDE: AN UNEXPECTED CASE OF SECONDARY CARBO-PIANCATELLI REARRANGEMENT

Authors

  • Andrey V. Gutnov Head of Chemistry, Chiroblock GmbH
  • Vladimir T. Abaev
  • Oleg P. Demidov North Caucasus Federal University, 2a Kulakova St., Stavropol 355029, Russia

DOI:

https://doi.org/10.1007/4785

Keywords:

boric acid, furfural, 2-naphthol, Betti reaction, carbo-Piancatelli rearrangement, multicomponent reaction

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.

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Published

2019-04-11

Issue

Vol. 55 No. 3 (2019)

Section

Short Communications