New synthesis of naphtho[2,1-b]furan derivatives from 1,2-dihydroxy-4-naphthyl-Β-dicarbonyl compounds

✍ Scribed by A. N. Grinev; I. K. Sorokina; G. A. Bogdanova

• Book ID: 104781711
• Publisher: Springer US
• Year: 1991
• Tongue: English
• Weight: 228 KB
• Volume: 27
• Category: Article
• ISSN: 0009-3122
• DOI: 10.1007/bf00473987

✦ Synopsis

A method for obtaining 4-acetonyl (4-phenacyl) derivatives

of 1,2-dioxo-

and

1,2

-dihydroxynaphthalenes is proposed. The previously unknown naphtho[2,1-b]furan o-quinones were synthesized from the latter derivatives. The aim of the present research was to study the possibility of using the previously obtained [1] fl-keto esters Ia,b, substituted with a dihydroxynaphthyl residue, in the synthesis of naphtho[2,1-b]furan derivatives that contain an oquinone fragment. The first stage of this research was the study of the possibility of obtaining 4-acetonyl(4-phenacyl)-l,2dihydroxynaphthalenes IIa,b from keto esters Ia,b. It was found that the best way to carry out the decarboxylation is to heat esters Ia,b in acetic acid in the presence of catalytic amounts of H2SO4; esterification of the acetic acid with subsequent spontaneous decarboxylation of the resulting acetoacetic (benzoylacetic) acid A evidently occurs in this case