A Protocol to 2-Aminobenzimidazoles via Copper-Catalyzed Cascade Addition and Cyclization of o-Haloanilines and Carbodiimides

被引：76
|
作者：
Wang, Fei [1 ]
Cai, Shangjun [1 ]
Liao, Qian [1 ]
Xi, Chanjuan [1 ]
机构：
[1] Tsinghua Univ, Dept Chem, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Minist Educ, Beijing 100084, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 09期
基金：
中国国家自然科学基金;
关键词：
PHASE COMBINATORIAL SYNTHESIS; NITROGEN BOND FORMATION; ONE-POT SYNTHESIS; NF-KAPPA-B; BENZIMIDAZOLE DERIVATIVES; EFFICIENT SYNTHESIS; AMINATION PROCESS; SNAR REACTION; INDOLES; INHIBITORS;
D O I：
10.1021/jo200014v
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient strategy for the synthesis of a variety of 2-animobenzimidazole derivatives has been developed. The reaction proceeded from o-haloanilines and carbodiimides via copper(I)-catalyzed domino reaction in the presence of tert-butoxide to afford the corresponding 2-animobenzimidazole derivatives in good to excellent yields. o-Haloanilines could be o-iodoaniline, o-bromoaniline, and o-chloroaniline derivatives. Carbodiimides could be symmetrical and unsymmetrical substrates with aryl or alkyl substituents. The reaction exhibited a good regioselectivity when unsymmetrical carbodiimides were employed.
引用
收藏
页码：3174 / 3180
页数：7
相关论文
共 50 条
  • [1] Copper-catalyzed synthesis of 2-aminobenzimidazoles from carbonimidoyl dichlorides and amines
    Yu, Hui
    Liu, Qiong
    Li, Yuzhe
    Ni, Chongzhi
    TETRAHEDRON LETTERS, 2012, 53 (39) : 5253 - 5256
  • [2] Synthesis of Indoles by Conjugate Addition and Ligand-Free Copper-Catalyzed Intramolecular Arylation of Activated Acetylenes with o-Haloanilines
    Gao, Detian
    Parvez, Masood
    Back, Thomas G.
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (48) : 14281 - 14284
  • [3] Copper-catalyzed synthesis of quinazolines via cascade cyclization/hydrodehalogenation
    Ma, Peng
    Wang, Yuhang
    Wang, Jianhui
    Ma, Ning
    NEW JOURNAL OF CHEMISTRY, 2023, 47 (19) : 9377 - 9382
  • [4] Synthesis of Benzoxazole and Benzimidazole Derivatives via Ligand-Free Copper(I)-Catalyzed Cross-Coupling Reaction of o-Halophenols or o-Haloanilines with Carbodiimides
    Shen, Guodong
    Bao, Weiliang
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (06) : 981 - 986
  • [5] Ligand-Free Copper-Catalyzed Synthesis of Substituted Benzimidazoles, 2-Aminobenzimidazoles, 2-Aminobenzothiazoles, and Benzoxazoles
    Saha, Prasenjit
    Ramana, Tamminana
    Purkait, Nibadita
    Ali, Md Ashif
    Paul, Rajesh
    Punniyamurthy, Tharmalingam
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (22): : 8719 - 8725
  • [6] Copper-Catalyzed CNH2 Arylation of 2-Aminobenzimidazoles and Related C-Amino-NH-azoles
    Rao, Desaboini Nageswar
    Rasheed, Sk.
    Kumar, Karampoori Anil
    Reddy, Annem Siva
    Das, Parthasarathi
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (13) : 2126 - 2133
  • [7] Copper-Catalyzed Decarboxylative Cascade Cyclization for the Synthesis of 2-Arylquinolines
    Chatterjee, Rana
    Pothireddy, Mohanreddy
    Dandela, Rambabu
    SYNLETT, 2023, 34 (09) : 1058 - 1062
  • [8] Copper-Catalyzed Cascade Addition/Cyclization: An Efficient and Versatile Synthesis of N-Substituted 2-Heterobenzimidazoles
    Lv, Xin
    Bao, Weiliang
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15): : 5618 - 5621
  • [9] Copper-Catalyzed Synthesis of Trisubstituted Isoxazoles via a Cascade Cyclization-Migration Process
    Ueda, Masafumi
    Sugita, Shoichi
    Sato, Aoi
    Miyoshi, Tetsuya
    Miyata, Okiko
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (20): : 9344 - 9351
  • [10] Construction of Phosphorothiolated 2-Pyrrolidinones via Photoredox/Copper-Catalyzed Cascade Radical Cyclization/Phosphorothiolation
    Zhang, Pengbo
    Li, Wenwu
    Yang, Shuai
    Qu, Weilong
    Wang, Longyu
    Lin, Jinming
    Gao, Xia
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (07): : 4947 - 4957
12345