Copper-Catalyzed Annulation of Electrophilic Benzannulated Heterocycles with 2-Aminopyridine and 2-Aminoquinoline: Direct Access toward Polyring-Fused Imidazo[1,2-a]pyridines

被引：9
|
作者：
Babu, Sheba Ann [1 ,2 ]
Varsha, P. V. [1 ]
Poulose, Susanna [1 ,2 ]
Varughese, Sunil [1 ,2 ]
John, Jubi [1 ,2 ]
机构：
[1] CSIR Natl Inst Interdisciplinary Sci & Technol CSI, Chem Sci & Technol Div, Thiruvananthapuram 695019, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 14期
关键词：
FIELD-EFFECT TRANSISTORS; METAL-FREE SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; HIGH-PERFORMANCE; 3-NITROINDOLES; DERIVATIVES; PALLADIUM; AMINOPYRIDINES; NITROOLEFINS; HETEROACENES;
D O I：
10.1021/acs.joc.3c00849
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We have developed a direct method for the synthesis ofpolyring-fusedimidazo[1,2-a]pyridines via a copper-catalyzed annulationof electrophilic benzannulated heterocycles with 2-aminopyridine and2-aminoquinoline. From 3-nitroindoles and 2-aminopyridine, we couldsynthesize tetracenes, viz., indole-fused imidazo[1,2-a]pyridines, and by starting from 2-aminoquinoline, we could generatepentacenes, viz., indolo-imidazo[1,2-a]quinolines.In addition, we could also extend the methodology toward the synthesisof benzothieno-imidazo[1,2-a]pyridines starting from3-nitrobenzothiophene. Furthermore, the basic photophysical propertiesof these synthesized heteroacenes were evaluated.
引用
收藏
页码：10027 / 10039
页数：13
相关论文
共 47 条
  • [11] Copper catalyzed tandem oxidative C-H amination/cyclizations: Direct access to imidazo[1,2-a]pyridines
    Pericherla, Kasiviswanadharaju
    Kaswan, Pinku
    Khedar, Poonam
    Khungar, Bharti
    Parang, Keykavous
    Kumar, Anil
    RSC ADVANCES, 2013, 3 (41): : 18923 - 18930
  • [12] Copper-Catalyzed Oxidative [3+2] Cycloaddition of N-Alkyl Pyridinium Salts to Imidazo[1,2-a]pyridines
    Zhang, Yuan
    Fan, Weibin
    Li, Yinghua
    Huang, Deguang
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (17): : 12244 - 12250
  • [13] Pd-catalyzed annulation of imidazo[1,2-a]pyridines with coumarins and indoles: synthesis of benzofuran and indole fused heterocycles (vol 58, pg 1585, 2022)
    Semwal, Rashmi
    Badhani, Gaurav
    Adimurthy, Subbarayappa
    CHEMICAL COMMUNICATIONS, 2022, 58 (17) : 2930 - 2930
  • [14] Copper-Promoted Annulation of Terminal Alkynes with 2-Aminopyridines to Assemble 2-Halogenated Imidazo[1,2-a]pyridines
    Liu, Yun
    Zhang, Yuxuan
    Sun, Jinwei
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (10) : 2804 - 2810
  • [15] Copper( II)-Catalyzed Aerobic Oxidative Coupling between Chalcone and 2-Aminopyridine via C HAmination:AnExpedientSynthesis of 3-AroylimidazoACHTUNGTRENUNG[ 1,2-a] pyridines
    Monir, Kamarul
    Bagdi, Avik Kumar
    Mishra, Subhajit
    Majee, Adinath
    Hajra, Alakananda
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (05) : 1105 - 1112
  • [16] Synthesis of Fused Tetracyclic Compounds via Oxidative Annulation: Access to Copper-Catalyzed Indolo[1,2-a]quinolines and to Ruthenium-Catalyzed Isoquinolin-1[2H]-ones
    Mali, Maruti
    Patil, Shashikant
    Sridhar, Balasubramanian
    Ghosh, Subhash
    Carboni, Bertrand
    Berree, Fabienne
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (09): : 5772 - 5779
  • [17] Copper-catalyzed formal [1+2+2]-annulation of alkyne-tethered diazoacetates and pyridines: access to polycyclic indolizines
    Dong, Shanliang
    Huang, Jingjing
    Sha, Hongkai
    Qiu, Lihua
    Hu, Wenhao
    Xu, Xinfang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (10) : 1926 - 1932
  • [18] CuBr catalyzed aerobic oxidative coupling of 2-aminopyridines with cinnamaldehydes: direct access to 3-formyl-2-phenyl-imidazo[1,2-a]pyridines
    Bharate, Jaideep B.
    Abbat, Sheenu
    Bharatam, Prasad V.
    Vishwakarma, Ram A.
    Bharate, Sandip B.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (28) : 7790 - 7794
  • [19] Au-catalyzed domino process synthesis of imidazo[1,2-a]pyridines from 2-aminopyridine and N-tosylhydrazones: An efficient C-N bond formation reaction
    Guo, Pengfeng
    Huang, Shuyu
    Mo, Jiaxian
    Chen, Xiaoyan
    Jiang, Hangqi
    Chen, Weifeng
    Cai, Hehuan
    Zhan, Haiying
    CATALYSIS COMMUNICATIONS, 2017, 90 : 43 - 46
  • [20] Hypervalent iodine in synthesis. 94. A facile synthesis of 2-substituted-imidazo[1,2-a]pyridines by cyclocondensation of alkynyl(phenyl) iodonium salts and 2-aminopyridine
    Liu, Z
    Chen, ZC
    Zheng, QG
    SYNTHETIC COMMUNICATIONS, 2004, 34 (02) : 361 - 367
12345