Journal of Organic Chemistry p. 3762 - 3768 (1986)
Update date:2022-08-03
Topics:
Smith, James G.
Dibble, Peter W.
Sandborn, Richard E.
The syntheses of 1,3-dihydro-1- and 1,3-dihydro-3-hydroxynaphtho<1,2-c>furan are described.Upon treatment with acid, these compounds undergo 1,4-elimination of water to generate the reactive naphtho<1,2-c>furan, 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-hydroxynaphtho<2,3-c>furan, which exists in tautomeric equilibrium with 3-(hydroxymethyl)-2-naphthaldehyde, serves as a convenient source of naphtho<2,3- c>furan.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.
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