Magnetic MOF‐199‐Catalyzed Synthesis of Benzo[4,5]imidazo[1,2‐f]phenanthridines and Their Analogues by Tandem C(sp2)−C Coupling and Cyclization Followed by Aromatization

Author:

Kim Min Jeong1ORCID,Lee Seong Weon1ORCID,Dao Pham Duy Quang1ORCID,Cho Chan Sik1ORCID

Affiliation:

1. Department of Applied Chemistry Kyungpook National University 80 Daehakro, Bukgu Daegu 41566 Republic of Korea

Abstract

AbstractTreatment of 2‐(2‐bromoaryl)‐ and 2‐(2‐bromovinyl)benzimidazoles with cyclohexane‐1,3‐diones in DMF in the presence of reusable Fe3O4@SiO2@MOF‐199 along with L‐proline and Cs2CO3 afforded 2,3‐dihydrobenzo[4,5]imidazo[1,2‐f]phenanthridin‐4(1H)‐ones and 2,3‐dihydrobenzo[4,5]imidazo[1,2‐a]quinolin‐4(1H)‐ones, respectively, in moderate to good yields. Such C(sp2)−C coupled and cyclized scaffolds were aromatized to benzo[4,5]imidazo[1,2‐f]phenanthridines and benzo[4,5]imidazo[1,2‐a]quinolines in good yields by a one‐pot sequential treatment with NaBH4, POCl3/pyridine, and DDQ.

Publisher

Wiley

Subject

General Chemistry

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