Synthesis of Pyrrolone‐ and Isoindolinone‐Fused Benzimidazole‐4, 7‐diones by Stepwise Palladium‐Catalyzed Carbonylative Cyclization and Oxidation. Issue 9 (20th August 2019)

• Record Type: Journal Article
• Authors: Kim, Dong Young; Dao, Pham Duy Quang; Yoon, Nam Sik; Cho, Chan Sik
• Is Part Of: Asian journal of organic chemistry. Volume 8:Issue 9(2019)
• Page Start: 1726
• Page End: 1731
• Publication Date: 2019-08-20
• Subjects: carbonylation -- cyclization -- oxidation -- nitrogen heterocycles -- palladium; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201900423
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: 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 PdCl2 and PPh3 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‐H2 O gives unprecedented pyrrolone‐ and isoindolinone‐fused benzimidazole‐4, 7‐diones in high yields. Abstract : N‐fused rings : The finding presented here is the synthesis of binuclear N‐fused hybrid scaffolds, pyrrolone‐ and isoindolinone‐fused benzimidazole‐4, 7‐diones by stepwise palladium‐catalyzed carbonylative cyclization and oxidation.