Copper(II)-Catalyzed Synthesis
of Benzo[<i>f</i>]pyrido[1,2-<i>a</i>]indole-6,11-dione
Derivatives via
Naphthoquinone Difunctionalization Reaction
Yun Liu
Jin-Wei Sun
10.1021/jo2023312.s002
https://acs.figshare.com/articles/dataset/Copper_II_Catalyzed_Synthesis_of_Benzo_i_f_i_pyrido_1_2_i_a_i_indole_6_11_dione_Derivatives_via_Naphthoquinone_Difunctionalization_Reaction/2557558
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.
2012-01-20 00:00:00
acyl bromide
oxidative aromatization
naphthoquinone
intramolecular cyclization
reaction scope
reaction mechanism
yield
acyl bromides