Synthesis of Binuclear Isoquinoline‐ and Pyridine‐Fused Benzimidazole‐4,7‐diones by Magnetic MOF‐199‐Catalyzed C–C Coupling/Cyclization Followed by Oxidation

2‐(2‐bromoaryl)‐4,7‐dimethoxy‐1H‐benzo[d]imidazoles and (Z)‐2‐(2‐bromovinyl)‐4,7‐dimethoxy‐1H‐benzo[d]imidazoles react with 1,3‐diketones by microwave irradiation in DMF in the presence of a catalytic amount of recyclable Fe3O4@SiO2@MOF‐199 along with a base to give binuclear isoquinoline‐ and pyrid...

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Bibliographic Details
Published in:European journal of organic chemistry 2019-07, Vol.2019 (25), p.4071-4079
Main Authors: Diep, Thi Duyen, Dao, Pham Duy Quang, Cho, Chan Sik
Format: Article
Language:English
Subjects:
Acetonitrile
Ammonium nitrate
Benzimidazole‐4,7‐dione
Catalysis
Cerium ammonium nitrate
Diketones
Ferric chloride
Heterocycles
Heterogeneous catalysis
Iron chlorides
Iron oxides
Isoquinoline
Oxidation
Pyridine
Silicon dioxide
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Summary:2‐(2‐bromoaryl)‐4,7‐dimethoxy‐1H‐benzo[d]imidazoles and (Z)‐2‐(2‐bromovinyl)‐4,7‐dimethoxy‐1H‐benzo[d]imidazoles react with 1,3‐diketones by microwave irradiation in DMF in the presence of a catalytic amount of recyclable Fe3O4@SiO2@MOF‐199 along with a base to give binuclear isoquinoline‐ and pyridine‐fused benzimidazoles, respectively. Treatment of such binuclear N‐fused hybrid scaffolds with ceric ammonium nitrate in acetonitrile/H2O or HBr/FeCl3 in H2O affords binuclear isoquinoline‐ and pyridine‐fused benzimidazole‐4,7‐diones in good to high yields. A new synthetic method of binuclear isoquinoline‐ and pyridine‐fused benzimidazole‐4,7‐diones via a recyclable copper‐catalyzed coupling and cyclization followed by oxidation has been developed.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201900635