Cyclization of sulfoxonium ylides with 2-aminopyridines towards imidazo [1,2-a]pyridines

被引：0
|
作者：
Luu, Vu H. [1 ,2 ]
Trinh, Hoang V. M. [1 ,2 ]
Tran, Dat H. [1 ,2 ]
Le, Tuong Q. [1 ,2 ]
Nguyen, Tung T. [1 ,2 ]
机构：
[1] Ho Chi Minh City Univ Technol HCMUT, VNU HCM Key Lab Struct Adv Mat, 268 Ly Thuong Kiet,Dist 10, Ho Chi Minh City, Vietnam
[2] Vietnam Natl Univ Ho Chi Minh City, Ho Chi Minh City, Vietnam
来源：
TETRAHEDRON LETTERS | 2025年 / 156卷
关键词：
Sulfoxonium ylides; Imidazo[1; a ]pyridines; Lewis acid catalyst; C-H AMINATION; CATALYST; FACILE;
D O I：
10.1016/j.tetlet.2024.155438
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A method for cyclization of 2-aminopyridines and sulfoxonium ylides is developed. The approach would avoid the requirement of pre-functionalized, Ortoleva-King typed alpha-haloketones for such cyclization. The annulation was facilitated in the presence of nickel(II) bromide, presumably as the Lewis acid catalyst. An array of functionalities including secondary amine, nitro, and halogen groups were tolerated. Two examples of alkyl sulfoxonium ylides were also presented. Our method feature a new approach to afford synthetically useful C 2substituted imidazo[1,2-a]pyridines from derivatives of benzoic acids.
引用
收藏
页数：3
相关论文
共 50 条
  • [21] Phospharylated imidazo[1,2-a]pyridines
    Tolmachev, AA
    Yurchenko, AA
    Kozlov, ES
    Merkulov, AS
    Semenova, MG
    Pinchuk, AM
    HETEROATOM CHEMISTRY, 1995, 6 (05) : 419 - 432
  • [22] DIASTEREOISOMERIC IMIDAZO[1,2-A]PYRIDINES
    KUBIK, R
    NEMECEK, J
    BOHM, S
    HRADILEK, M
    KUTHAN, J
    MENDELEEV COMMUNICATIONS, 1995, (01) : 29 - 30
  • [23] Iron(III)-catalyzed synthesis of 3-aroylimidazo[1,2-a]pyridines from 2-aminopyridines and ynals
    Chen, Zhengwang
    Liu, Botao
    Liang, Pei
    Yang, Zhixiong
    Ye, Min
    TETRAHEDRON LETTERS, 2018, 59 (07) : 667 - 670
  • [24] Photoisomerization of imidazo[1,2-a]pyridines
    Kubik, R
    Bohm, S
    Havlicek, V
    Kuthan, J
    MENDELEEV COMMUNICATIONS, 1996, (06) : 225 - 226
  • [25] SYNTHESIS OF IMIDAZO[1,2-A]PYRIDINES DIRECTLY FROM METHYLKETONES OR METHYLENEKETONES - IODATION OF IMIDAZO[1,2-A]PYRIDINES
    SALDABOL, NO
    HILLER, SA
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1976, (10): : 1396 - 1405
  • [26] 2,3-Disubstituted imidazo[1,2-a]pyridines from 2-aminopyridines and acetophenones. Catalyst's efficiency and solid state NMR study.
    Kurteva, V. B.
    Lubenov, L. A.
    Simova, S. D.
    BULGARIAN CHEMICAL COMMUNICATIONS, 2014, 46 : 47 - 52
  • [27] Metal- and base-free synthesis of imidazo[1,2-a]pyridines through elemental sulfur-initiated oxidative annulation of 2-aminopyridines and aldehydes
    Tan, Jing
    Ni, Penghui
    Huang, Huawen
    Deng, Guo-Jun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (23) : 4227 - 4230
  • [28] Electrochemical Synthesis of 3-Bromoimidazo[1,2-a]pyridines Directly from 2-Aminopyridines and alpha-Bromoketones
    Jian, Wen-Qian
    Wang, Hai-Bin
    Du, Ke-Si
    Zhong, Wei-Qiang
    Huang, Jing-Mei
    CHEMELECTROCHEM, 2019, 6 (10): : 2733 - 2736
  • [29] IMMUNOMODULATORY PYRROLO[1,2-A]IMIDAZOLES AND IMIDAZO[1,2-A]PYRIDINES
    MURRAY, RJ
    LOCH, JT
    DAVIDSON, TA
    RADOV, LA
    GAWLAK, DL
    KAMP, D
    TRUSSO, LA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1986, 192 : 81 - MEDI
  • [30] Synthesis of Imidazo[1,2-a]pyridines by the Bis(acetyloxy)(phenyl)-λ3-iodane-Mediated Oxidative Coupling of 2-Aminopyridines with β-Keto Esters and 1,3-Diones
    Wang, Xianpei
    Ma, Lijuan
    Yu, Wei
    SYNTHESIS-STUTTGART, 2011, (15): : 2445 - 2453
12345