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

被引：1
|
作者：
Kim, Min Jeong [1 ]
Lee, Seong Weon [1 ]
Dao, Pham Duy Quang [1 ]
Cho, Chan Sik [1 ]
机构：
[1] Kyungpook Natl Univ, Dept Appl Chem, 80 Daehakro, Daegu 41566, South Korea
来源：
CHEMISTRYSELECT | 2023年 / 8卷 / 29期
关键词：
C-C coupling; cyclization; magnetic MOF-199 catalyst; N-fused heterocycles; aromatization; METAL-ORGANIC FRAMEWORK; ONE-POT SYNTHESIS; BENZIMIDAZOLE-FUSED PHENANTHRIDINES; C-C; EFFICIENT; 2-ARYLBENZIMIDAZOLES; CONSTRUCTION; DERIVATIVES; ARYLATION; CATALYST;
D O I：
10.1002/slct.202300926
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Treatment 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(sp(2))-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.
引用
收藏
页数：6
相关论文
共 50 条
  • [1] Synthesis of Imidazo[1,2-f]phenanthridines by Recyclable Magnetic MOF-Catalyzed Coupling and Cyclization of 2-(2-Bromoaryl)imidazoles with Cyclohexane-1,3-diones Followed by Aromatization
    Lee, Seong Weon
    Pham Duy Quang Dao
    Lim, Ho-Jin
    Cho, Chan Sik
    ACS OMEGA, 2022, 7 (22): : 18486 - 18497
  • [2] Copper-catalyzed C-C coupling and cyclization: Synthesis of benzo [4,5] imidazo[1,2-a] pyridines and benzo[4,5] imidazo[2,1-a] isoquinolines
    Yang, Byeong Woo
    Pham Duy Quang Dao
    Yoon, Nam Sik
    Cho, Chan Sik
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2017, 851 : 136 - 142
  • [3] Recyclable Magnetic Cu-MOF-74-Catalyzed C(sp2)-N Coupling and Cyclization under Microwave Irradiation: Synthesis of Imidazo[1,2-c]quinazolines and Their Analogues
    Lee, Seong Weon
    Dao, Pham Duy Quang
    Lim, Ho-Jin
    Cho, Chan Sik
    ACS OMEGA, 2023, 8 (18): : 16218 - 16227
  • [4] The Synthesis of Imidazo[1,2-f]phenanthridines, Phenanthro[9,10-d]imidazoles, and Phenanthro[9′, 10′:4,5]imidazo[1,2-f]phenanthridines via Intramolecular Oxidative Aromatic Coupling
    Skonieczny, Kamil
    Jazwinski, Jaroslaw
    Gryko, Daniel T.
    SYNTHESIS-STUTTGART, 2017, 49 (20): : 4651 - 4662
  • [5] Synthesis of Imidazo[1,2-f]phenanthridines through Palladium-Catalyzed Intramolecular C-C Bond Formation
    Saini, Hitesh Kumar
    Dhiman, Shiv
    Pericherla, Kasiviswanadharaju
    Kumar, Anil
    SYNTHESIS-STUTTGART, 2015, 47 (23): : 3727 - 3732
  • [6] Synthesis of Benzo[4,5] imidazo[1,2-c] pyrimidin-1-amines and Their Analogs via Copper-Catalyzed C-N Coupling and Cyclization
    Pham Duy Quang Dao
    Lee, Ha Kyeong
    Sohn, Ho-Sang
    Yoon, Nam Sik
    Cho, Chan Sik
    ACS OMEGA, 2017, 2 (06): : 2953 - 2958
  • [7] Synthesis of Quinolino[3′,4′:4,5] pyrrolo[1,2-f]phenanthridines by Regioselective Sonogashira Reaction Followed by Domino C-N Coupling/Hydroamination/C-H Arylation
    Ngo Nghia Pham
    Salman, Ghazwan Ali
    Ponce, Marian Blanco
    Tuan Thanh Dang
    Spannenberg, Anke
    Ehlers, Peter
    Langer, Peter
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (26) : 3865 - 3873
  • [8] Palladium(0)-catalyzed Domino C-N Coupling/Hydroamination/C-H Arylation: Efficient Synthesis of Benzothieno[2′,3′:4,5]pyrrolo[1,2-f]phenanthridines
    Salman, Ghazwan Ali
    Ngo Nghia Pham
    Thang Ngoc Ngo
    Ehlers, Peter
    Villinger, Alexander
    Langer, Peter
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (08) : 1402 - 1406
  • [9] Synthesis of Binuclear Isoquinoline- and Pyridine-Fused Benzimidazole-4,7-diones by Magnetic MOF-199-Catalyzed C-C Coupling/Cyclization Followed by Oxidation
    Thi Duyen Diep
    Pham Duy Quang Dao
    Cho, Chan Sik
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (25) : 4071 - 4079
  • [10] Pd(OAc)2-Catalyzed Synthesis of Imidazo[1,2-f]phenanthridines via a Sequential Ullmann Coupling and Oxidative Coupling Dehydrogenation
    Li, Ye
    Liang, Tongwei
    Liu, Jian-Quan
    Wang, Xiang-Shan
    JOURNAL OF ORGANIC CHEMISTRY, 2025, 90 (01): : 1 - 7
12345