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Synthesis of Pyrrolone‐ and Isoindolinone‐Fused Benzimidazole‐4,7‐diones by Stepwise Palladium‐Catalyzed Carbonylative Cyclization and Oxidation
Author(s) -
Kim Dong Young,
Dao Pham Duy Quang,
Yoon Nam Sik,
Cho Chan Sik
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900423
Subject(s) - chemistry , catalysis , benzimidazole , toluene , palladium , acetonitrile , carbon monoxide , carbonylation , combinatorial chemistry , ceric ammonium nitrate , medicinal chemistry , organic chemistry , polymer , grafting
2‐(2‐Bromovinyl)‐ and 2‐(2‐bromoaryl)‐4,7‐dimethoxybenzimidazoles react with carbon monoxide (10 atm) in toluene in the presence of a catalytic amount of PdCl 2 and PPh 3 along with NaOAc to produce the corresponding pyrrolone‐ and isoindolinone‐fused 4,7‐dimethoxybenzimidazoles, respectively, in good yields. Oxidation of such binuclear N‐fused hybrid scaffolds with ceric ammonium nitrate in acetonitrile‐H 2 O gives unprecedented pyrrolone‐ and isoindolinone‐fused benzimidazole‐4,7‐diones in high yields.