Pd(II)-Catalyzed Benzimidazole-Assisted Annulation of 3-(1H-Benzo[d]imidazol-2-yl)-2H-chromen-2-one: Access to Imidazo[1,2-a]chromeno[3,4-c]pyridine

被引：1
|
作者：
Singla, Dinesh [1 ]
Luxami, Vijay [1 ]
Paul, Kamaldeep [1 ]
机构：
[1] Thapar Inst Engn & Technol, Sch Chem & Biochem, Patiala 147001, India
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 26卷 / 34期
关键词：
coumarin; C-H functionalization; Lippert Plot; oxidative annulation; palladium; CATALYZED OXIDATIVE ANNULATION; H FUNCTIONALIZATION; BIS-COUMARINS; DERIVATIVES; ALKYLATION;
D O I：
10.1002/ejoc.202300531
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Palladium-catalyzed [4+2] oxidative annulation of coumarin-benzimidazoles with olefins for the synthesis of polycyclic aromatic hydrocarbons have been achieved. This synthetic protocol gives access to a wide range of structurally distinct imidazo[1,2-a]chromeno[3,4-c]pyridines in moderate to good yield with wide functional group tolerance. Further, photophysical properties of annulated scaffolds have been examined, which discloses their interesting solvatochromic emission behaviors.
引用
收藏
页数：5
相关论文
共 50 条
  • [41] Crystal structure of {tris((1H-benzo[d]imidazol-2-yl)methyl)amine-κ4N,N′, N",N"′}-(nitrito-κ2O,O′)nickel(II) perchlorate - ethanol (1/1), C26H27ClN8NiO7
    Li, Xin-Lun
    Luo, Zhong-Ping
    Zhang, Jun-Chao
    Nie, Feng-Mei
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2020, 235 (04): : 767 - 769
  • [42] Synthesis of Some Novel 3-Alkyl/aryl-6-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles
    Chen, Xiqing
    Liu, Chenjiang
    Wang, Jide
    Li, Yanping
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2010, 47 (05) : 1225 - 1229
  • [43] Green Synthesis of 1H-Benzo[d]Imidazol-2-yl-4-(Aryldiazenyl)Phenol and Bis Benzo[d]Imidazoles Using Fe3O4@Silicapropyl@Vanillin/Thiamin Nanoparticles
    Fekri, Leila Zare
    Hojjati-Zolpirani, Zahra
    Kadivar-Kalmarzi, Mohaddeseh
    POLYCYCLIC AROMATIC COMPOUNDS, 2023, 43 (07) : 6291 - 6305
  • [44] Synthesis, characterization, biological evaluation and molecular docking studies of 2-(1H-benzo[d] imidazol-2-ylthio)-N-(substituted 4-oxothiazolidin-3-yl) acetamides
    Yadav, Snehlata
    Narasimhan, Balasubramanian
    Lim, Siong M.
    Ramasamy, Kalavathy
    Vasudevan, Mani
    Shah, Syed Adnan Ali
    Selvaraj, Manikandan
    CHEMISTRY CENTRAL JOURNAL, 2017, 11
  • [45] Cu-Catalyzed Oxidative [3+2] Annulation of 2-(Pyridine-2-yl)acetates with Maleimides: Synthesis of 1H-Pyrrolo[3,4-b]indolizine-1,3-diones
    Lv, Kai-Hong
    Zhao, Qing-Sheng
    Zhao, Ke-Hua
    Yang, Jia-Ming
    Yan, Sheng-Jiao
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (22): : 15301 - 15311
  • [46] Ru(<sc>ii</sc>)-catalyzed oxidative (4+3) C-H/C-H annulation of 2-aryl-4H-pyrido[1,2-a]pyrimidin-4-ones with allyl alcohol
    Jangir, Tarun
    Nipate, Dhananjay S.
    Rangan, Krishnan
    Kumar, Anil
    CHEMICAL COMMUNICATIONS, 2025,
  • [47] Formation of epoxychromeno[4,3-c]isoquinolines through diastereoselective one-pot IMDA reaction of 4-chloro-3-[(1E)-3-oxo-3-phenyl-1-propen-1-yl]-2H-chromen-2-one and furfurylamine
    Alizadeh, Abdolali
    Amir Ashjei Asalemi, Kaveh
    Farajpour, Behnaz
    Halvagar, Mohammad Reza
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2020, 17 (12) : 3393 - 3399
  • [48] Planarity of substituted pyrrole and furan rings in (3R*, 1'S*, 3'R*)-3-(1'-tert-butylamino-1'H, 3'H-benzo[c] furan-3'- yl)-2-tert-butyl-2,3-dihydro-1H-benzo[c] pyrrol-1-one
    Dazie, Joel Donkeng
    Liska, Alan
    Ludvik, Jiri
    Fabry, Jan
    Dusek, Michal
    Eigner, Vaclav
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-CRYSTALLINE MATERIALS, 2017, 232 (06): : 441 - 452
  • [49] Design, synthesis, and application of 1H-imidazol-3-ium trinitromethanide {[HIMI]C(NO2)3} as a recyclable nanostructured ionic liquid (NIL) catalyst for the synthesis of imidazo[1,2-a]pyrimidine-3-carbonitriles
    Yarie, Meysam
    Zolfigol, Mohammad Ali
    Baghery, Saeed
    Khoshnood, Abbas
    Alonso, Diego A.
    Kalhor, Mehdi
    Bayat, Yadollah
    Asgari, Asiye
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2018, 15 (10) : 2259 - 2270
  • [50] Microwave-Assisted Palladium-catalyzed double C-H Activation: One-pot Synthesis of Benzo[a]imidazo[5,1,2-cd]indolizines from 2-Phenylimidazo[1,2-a]pyridines and 1,2-Diiodobenzene
    Prajapati, Ronak, V
    Prajapati, Vaibhav D.
    Purohit, Vishal B.
    Avalani, Jemin R.
    Kamani, Ronak D.
    Sapariya, Nirav H.
    Karad, Sharad C.
    Raval, Dipak K.
    CHEMISTRYSELECT, 2022, 7 (24):
12345