65539-69-7Relevant articles and documents
The Preparation and Reactions of Naphthofuran and Naphthofuran
Smith, James G.,Dibble, Peter W.,Sandborn, Richard E.
, p. 3762 - 3768 (1986)
The syntheses of 1,3-dihydro-1- and 1,3-dihydro-3-hydroxynaphthofuran are described.Upon treatment with acid, these compounds undergo 1,4-elimination of water to generate the reactive naphthofuran, which is trapped in situ by a variety of dienophiles.Aromatization of the resulting adducts gives access to 2,3-disubstituted phenanthrenes or benzanthracenes.In addition, it has been shown that the hemiacetal, 1,3-dihydro-1-hydroxynaphthofuran, which exists in tautomeric equilibrium with 3-(hydroxymethyl)-2-naphthaldehyde, serves as a convenient source of naphthofuran.This furan can also be trapped by a variety of dienophiles.The resulting Diels-Alder adducts can be aromatized, giving substituted anthracenes.The use of aromatic 1,4-quinones as dienophiles leads to linear polycyclic aromatic quinones of four to seven rings.