Hypervalent iodine(III)-induced intramolecular cyclization of alpha-(aryl)alkyl-beta-dicarbonyl compounds: a convenient synthesis of benzannulated and spirobenzannulated compounds.
A novel hypervalent iodine(III)-induced direct intramolecular cyclization of alpha-(aryl)alkyl-beta-dicarbonyl compounds has been described. Both meta- and para-substituted phenol ether derivatives containing acyclic or cyclic 1,3-dicarbonyl moieties at the side chain undergo this reaction in a facile manner. The reactions afford benzannulated and spirobenzannulated compounds that are of biological importance. The reaction is found to be general, mild, and high yielding. The mechanism of the reaction has been shown to involve a cation radical intermediate.
Arisawa
M
M
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan.
Ramesh
N G
NG
Nakajima
M
M
Tohma
H
H
Kita
Y
Y