Iodine Mediated Annulation of Triethylamine, Aldehydes and 2-Aminopyridines for the Synthesis of 3-Formyl-Imidazo [1,2-a]pyridine Derivatives

被引：2
|
作者：
Zhang, Wenqing [1 ]
Shen, Lihong [2 ]
Zhang, Jun [1 ]
机构：
[1] Ningxia Univ, Coll Chem & Chem Engn, Yinchuan 750021, Ningxia, Peoples R China
[2] Handan Univ, Hebei Key Lab Heterocycl Cpds, Handan 056005, Hebei, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2024年 / 366卷 / 18期
关键词：
heterocycle; formylation; iodine; triethylamine; annulation; TERTIARY-AMINES; FORMYLATION;
D O I：
10.1002/adsc.202400473
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
With triethylamine as a synthon, an alternative method for the synthesis of 3-formyl imidazo[1,2-a]pyridines has been accomplished from aldehydes, and 2-aminopyridines. The reaction proceeded via iodine-catalyzed C-N bond cleavage of triethylamine, generation of alpha,beta-unsaturated aldehyde in situ, and oxidative cyclization with air as the oxygen source. This protocol may facilitate the synthesis of imidazo[1,2-a]pyridine derivatives and provide a reference for the usage of triethylamine as a synthon. image
引用
收藏
页码：3796 / 3801
页数：6
相关论文
共 50 条
  • [21] A NEW SYNTHESIS OF IMIDAZO[1,2-A]PYRIDINE AND IMIDAZO[2,1-A]ISOQUINOLINE DERIVATIVES
    TOMINAGA, Y
    MOTOKAWA, S
    SHIROSHITA, Y
    HOSOMI, A
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1987, 24 (05) : 1365 - 1369
  • [22] Synthesis of imidazo[1,2a]pyridines via three-component reaction of 2-aminopyridines, aldehydes and alkynes
    Liu, Ping
    Fang, Li-song
    Lei, Xinsheng
    Lin, Guo-qiang
    TETRAHEDRON LETTERS, 2010, 51 (35) : 4605 - 4608
  • [23] Visible Light Driven Coupling of 2-aminopyridines and α-Keto Vinyl Azides for the Synthesis of Imidazo[1,2-a]pyridines and Their Cytotoxicity
    Adiyala, Praveen Reddy
    Sastry, Kasinathuni Naga Visweswara
    Kovvuri, Jeshma
    Nagarajan, Apoorva
    Reddy, Velma Ganga
    Bin Sayeed, Ibrahim
    Nayak, Vedinthe Lakshma
    Maurya, Ram Awatar
    Kamal, Ahmed
    CHEMISTRYSELECT, 2017, 2 (26): : 8158 - 8161
  • [24] Cu-Pybox catalyzed synthesis of 2,3-disubstituted imidazo[1,2-a]pyridines from 2-aminopyridines and propargyl alcohol derivatives
    Cheng, Cang
    Ge, Luo
    Lu, Xuehe
    Huang, Jianping
    Huang, Haocheng
    Chen, Jie
    Cao, Weiguo
    Wu, Xiaoyu
    TETRAHEDRON, 2016, 72 (43) : 6866 - 6874
  • [25] Synthesis and antiepileptic studies of new imidazo[1,2-a]pyridine derivatives
    Ulloora, Shrikanth
    Adhikari, Airody Vasudeva
    Shabaraya, Ramakrishna
    CHINESE CHEMICAL LETTERS, 2013, 24 (09) : 853 - 856
  • [26] SYNTHESIS AND ANTIBACTERIAL ACTION OF SOME IMIDAZO[1,2-A]PYRIDINE DERIVATIVES
    SALDABOL, NO
    POPELIS, YY
    ALEKSEEVA, LN
    YALYNSKAYA, AK
    MOSKALEVA, ND
    KHIMIKO-FARMATSEVTICHESKII ZHURNAL, 1977, 11 (06): : 64 - 70
  • [27] A Convenient Synthesis of C-3-Aryloxymethyl Imidazo[1,2-a]Pyridine Derivatives
    Kona, Sridevi
    Ravi, Rama Suresh
    Chava, Venkata N. R.
    Perali, Ramu Sridhar
    JOURNAL OF CHEMISTRY, 2013, 2013
  • [28] Synthesis and antiepileptic studies of new imidazo[1,2-a]pyridine derivatives
    Shrikanth Ulloora
    Airody Vasudeva Adhikari
    Ramakrishna Shabaraya
    Chinese Chemical Letters, 2013, 24 (09) : 853 - 856
  • [29] Synthesis of 2-(1-adamantyl)imidazo [1,2-a]pyridine and 2-(1-adamantyl)imidazo[1,2-a]pyrimidine derivatives
    Matschay, A
    Skwarski, D
    Sobiak, S
    POLISH JOURNAL OF CHEMISTRY, 2000, 74 (12) : 1707 - 1712
  • [30] A copper-catalyzed synthesis of benzo[4,5]imidazo[1,2-a]pyridine derivatives via C-N bond formation of 2-aminopyridines with arylboronic acids
    Li, Xiao-Tang
    Han, Chuan-Jie
    Zhang, Zhan-Hui
    RESEARCH ON CHEMICAL INTERMEDIATES, 2025, 51 (04) : 1733 - 1747
12345