Copper(II)-Catalyzed Synthesis of Benzo[<i>f</i>]pyrido[1,2-<i>a</i>]indole-6,11-dione Derivatives via Naphthoquinone Difunctionalization Reaction
2012-01-20T00:00:00Z (GMT)
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Benzo[<i>f</i>]pyrido[1,2-<i>a</i>]indole-6,11-diones
have been synthesized in high yields by copper(II)-catalyzed three-component
reactions of acyl bromide, 1,4-naphthoquinone, and pyridine (or isoquinoline)
via sp<sup>2</sup>–C–H difunctionalization of naphthoquinone
followed by intramolecular cyclization and oxidative aromatization.
In an attempt to expand the reaction scope and to help clarify the
reaction mechanism, 1,3-dicarbonyl compounds are used in place of
acyl bromides to take part in this reaction, and the benzo[<i>f</i>]pyrido[1,2-<i>a</i>]indole-6,11-diones derivatives
are also obtained in excellent yields.
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