Open Access Open Access  Restricted Access Subscription Access

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

Andrey V. Gutnov, Vladimir T. Abaev, Oleg P. Demidov
Cover Image

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.

Keywords


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

Full Text: PDF Supplementary File(s): supplementary info (904KB)


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv