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Synthesis of Naphtho[2,1]-b]furanylium Cation and Its Reaction with Alcohols and Trialkyl Phosphites

Yavari I., Anary-Abbasinejad M., Hossaini Z.

Polish Journal of Chemistry

2004

Vol. 78 / nr 3

361-367

The reaction between dibenzoylacetylene and 2-naphthol in the presence of a catalytic amount of pyridine leads to 2-hydroxy-1-(2-oxo-2-phenylethylidene)-2-phenyl-1,2- dihydro-naphtho[2,1-b]furan in nearly quantitative yield. Treatment of this heterocyclic system with trimethyl chlorosilane in chloroform leads quantitatively to 1-(2-oxo-2- phenylethylidene)-2-phenyl-1H-naphtho[2,1-b]furanylium chloride. Addition of nucleophiles such as alcohols or trialkyl phosphites to this salt produces functionalized 1,2- dihydronaphthofuran derivatives in excellent yields.