Synthesis of benzo[4, 5]imidazo[1, 2‐a]indolo[1, 2‐c]quinazolines from 2‐(2‐bromoaryl)indoles and 2‐methoxybenzimidazoles under recyclable magnetic MOF‐199 catalysis. (29th August 2022)

• Record Type: Journal Article
• Authors: Kim, Min Jeong; Lee, Seong Weon; Dao, Pham Duy Quang; Cho, Chan Sik
• Is Part Of: Applied organometallic chemistry. Volume 36:Number 11(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-08-29
• Subjects: 2‐methoxybenzimidazole -- C‐N coupling -- cyclization -- N‐fused heterocycles -- recyclable copper catalyst; Organometallic chemistry -- Periodicals; Organometallic compounds -- Periodicals; 547.05
• DOI: 10.1002/aoc.6871
• Languages: English
• ISSNs: 0268-2605

Abstract

Abstract : 2‐(2‐Bromoaryl)indoles react with 2‐methoxybenzimidazoles in DMF in the presence of a catalytic amount of recyclable Fe3 O4 @SiO2 @MOF‐199 along with K2 CO3 to afford a series of benzo[4, 5]imidazo[1, 2‐ a ]indolo[1, 2‐ c ]quinazolines in good yields. The reaction applies to a broad scope of 2‐(2‐bromoaryl)indoles containing electron‐donating or ‐withdrawing substituents on bromophenyl and indole moieties, and alkyl substituents at 3‐position of indole moiety. A reaction pathway involving a copper‐catalyzed Ullmann‐type C (sp 2 )‐N coupling and an addition‐elimination nucleophilic aromatic substitution via Meisenheimer complex followed by cyclocondensation is proposed for this catalytic process. The Fe3 O4 @SiO2 @MOF‐199 catalyst could be recovered and reused several times without any change of catalytic activity. Abstract :