Ultrasound-Mediated Green Synthesis of Imidazo[1,2-a ]pyridines and Imidazo[2,1-b ]thiazoles through C(sp 3 )-H Functionalization

被引:0
作者
Chauhan, Swati [1 ]
Verma, Pratibha [2 ]
Srivastava, Vandana [2 ]
机构
[1] Gautam Buddha Univ, Sch Vocat Studies & Appl Sci, Dept Appl Chem, Greater Noida 201312, India
[2] Indian Inst Technol BHU, Dept Chem, Varanasi 221005, India
关键词
green chemistry; heterocycles; gram-scale synthesis; ultrasound; one-pot synthesis; ONE-POT SYNTHESIS; CATALYZED SYNTHESIS; POTASSIUM-IODIDE; DERIVATIVES; ACCESS; CONSTRUCTION; INHIBITORS; DISCOVERY; ALDEHYDES; LIGAND;
D O I
10.1055/s-0042-1751565
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An ultrasound-assisted expedient protocol has been developed for the synthesis of imidazo[1,2-a]pyridines and imidazo[2,1-b]thiazoles by the C-H functionalization of ketones using a KI/tert-butylhydroperoxide catalytic system. The reaction takes place in water, agreen solvent, and does not require a metal catalyst; it also gives goodyields of the products. The method offers numerous noteworthy char-acteristics, including mild reaction conditions, the absence of a base,broad functional-group compatibility, and excellent reaction yields.Moreover, it avoids the use of costly and air-sensitive chemicals, andcan be conducted under ambient reaction conditions.
引用
收藏
页码:1899 / 1905
页数:7
相关论文
共 50 条
  • [41] Synthesis of 3-Acyl and 2-Acyl Imidazo[1,2-a]pyridines by I2-Mediated Diamination of α,β-Unsaturated Ketones with 2-Aminopyridines
    Yu, Wenquan
    Song, Lina
    Tian, Xianhai
    Zhao, Ting
    Wang, Manman
    Wu, Jie
    Qiao, Yan
    Chang, Junbiao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (06) : 1530 - 1537
  • [42] Iodine-mediated C-N and C-S bond formation: regioselective synthesis of benzo[4,5]imidazo[2,1-b]thiazoles
    Ambethkar, Sethurajan
    Vellimalai, Muthalu
    Padmini, Vediappen
    Bhuvanesh, Nattamai
    NEW JOURNAL OF CHEMISTRY, 2017, 41 (01) : 75 - 80
  • [43] One-pot regioselective synthesis of new 5-(arylsulfonylamino)imidazo[2,1-b]thiazoles
    Serykh, Valery Y.
    Chernysheva, Gulnur N.
    Kondrashov, Evgeniy V.
    Vashchenko, Aleksandr V.
    Smirnov, Vladimir I.
    Rozentsveig, Igor B.
    ARKIVOC, 2015, : 377 - 391
  • [44] Copper-Catalyzed Regioselective C5 Sulfenylation of Imidazo[2,1-b]thiazoles with Thiols
    Liu, Wenjie
    Wang, Shaohua
    Jiang, Yi
    He, Peiling
    Zhang, Qi
    Cao, Hua
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (04) : 312 - 315
  • [45] Synthesis of 6-substituted imidazo[2,1-b]thiazoles via Pd/Cu-mediated Sonogashira coupling in water
    Kamali, Taghi A.
    Bakherad, Mohammad
    Nasrollahzadeh, Mahmoud
    Farhangi, Shiva
    Habibi, Davood
    TETRAHEDRON LETTERS, 2009, 50 (39) : 5459 - 5462
  • [46] Palladium-catalyzed site-selective C-H alkenylation of imidazo[2,1-b]thiazoles
    Huang, Guoli
    Teng, Mingyu
    Liu, Bo
    Rong, Meizhu
    Liu, Ying
    Chen, Yegao
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2016, 818 : 163 - 167
  • [47] Facile synthesis of imidazo[1,2-a]pyridines promoted by room-temperature ionic liquids under ultrasound irradiation
    Paengphua, Piyawat
    Chancharunee, Sirirat
    MONATSHEFTE FUR CHEMIE, 2018, 149 (10): : 1835 - 1840
  • [48] Pd-Cu-Mediated Synthesis of 2-Substituted Imidazo[1,2-A]pyridines in Water
    Bakherad, Mohammad
    Keivanloo, Ali
    Hashemi, Mahdieh
    SYNTHETIC COMMUNICATIONS, 2009, 39 (06) : 1002 - 1011
  • [49] Synthesis, crystal structures and spectral characterization of imidazo [1,2-a]pyrimidin-2-yl-acetic acid and related analog with imidazo[2,1-b]thiazole ring
    Dylong, Agnieszka
    Goldeman, Waldemar
    Sowa, Michal
    Slepokura, Katarzyna
    Drozdzewski, Piotr
    Matczak-Jon, Ewa
    JOURNAL OF MOLECULAR STRUCTURE, 2016, 1117 : 153 - 163
  • [50] Facile synthesis of imidazo[1,2-a]pyridines promoted by room-temperature ionic liquids under ultrasound irradiation
    Piyawat Paengphua
    Sirirat Chancharunee
    Monatshefte für Chemie - Chemical Monthly, 2018, 149 : 1835 - 1840