Iodine-Mediated Oxidative Annulation by C-C Cleavage: A Domino Synthetic Approach to Quinazolinones and Benzo[4,5]imidazo[1,2-c]quinazolines

被引:5
作者
Donthiboina, Kavitha [1 ]
Mani, Geeta Sai [1 ]
Shankaraiah, Nagula [1 ]
Kamal, Ahmed [1 ,2 ]
机构
[1] NIPER Hyderabad, Dept Med Chem, Hyderabad 500037, Andhra Pradesh, India
[2] Jamia Hamdard, SPER, New Delhi 110062, India
来源
CHEMISTRYSELECT | 2020年 / 5卷 / 13期
关键词
Annulation; Benzimidazo-quinazolines; C-C bond cleavage; Cleavage reactions; Copper iodide; Domino process; I-2; Quinazolinones; ONE-POT SYNTHESIS; CARBON BOND-CLEAVAGE; CONTAINING HETEROCYCLES; O-AMINOBENZAMIDES; N-HETEROCYCLES; ACTIVATION; CHEMISTRY; CONSTRUCTION; AMINES; QUINAZOLIN-4(3H)-ONES;
D O I
10.1002/slct.202000682
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A facile iodine-mediated unprecedented C-C cleavage by employing CuI has been established towards the synthesis of quinazolin-4(3H)-ones and benzo[4,5]imidazo[1,2-c]quinazolines. This protocol involves peroxide free synthetic approach for the stable C-C bond cleavage followed by oxidative annulation to develop a library of fused N-heterocyclic molecules.
引用
收藏
页码:3923 / 3928
页数:6
相关论文
共 33 条
  • [1] Copper-catalyzed C-C coupling and cyclization: Synthesis of benzo [4,5] imidazo[1,2-a] pyridines and benzo[4,5] imidazo[2,1-a] isoquinolines
    Yang, Byeong Woo
    Pham Duy Quang Dao
    Yoon, Nam Sik
    Cho, Chan Sik
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2017, 851 : 136 - 142
  • [2] An Extensive Analysis of Current Synthetic Methodologies and Applications of Imidazo/Benzimidazo[1,2-c]Quinazolines
    Bairy, Gurupada
    Sinha, Chittaranjan
    CHEMISTRYSELECT, 2024, 9 (22):
  • [3] An Efficient Synthesis of Pyrrolo[1,2-a] or Pyrido[1,2-a]benzo[4,5]imidazo[1,2-c]quinazoline Derivatives in Ionic Liquids Catalyzed by Iodine
    Wang, Yue
    Liu, Jian-Quan
    Wang, Xiang-Shan
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2017, 54 (06) : 3440 - 3446
  • [4] Synthesis of Benzo[4,5] imidazo[1,2-c] pyrimidin-1-amines and Their Analogs via Copper-Catalyzed C-N Coupling and Cyclization
    Pham Duy Quang Dao
    Lee, Ha Kyeong
    Sohn, Ho-Sang
    Yoon, Nam Sik
    Cho, Chan Sik
    ACS OMEGA, 2017, 2 (06): : 2953 - 2958
  • [5] Base/DMSO-Promoted Synthesis of Benzo[4,5]imidazo[2,1-a]isoquinolines via C-C Bond Formation
    Lee, Seong Weon
    Dao, Pham Duy Quang
    Lim, Ho-Jin
    Cho, Chan Sik
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (05) : 1182 - 1188
  • [6] Metal-Free, Photoredox-Catalyzed Synthesis of Quinazolin-4(3H)-ones and Benzo[4,5]imidazo[1,2-c]quinazolines Using Trialkylamines as Alkyl Synthon
    Arumugam, Ajithkumar
    Palani, Pushbaraj
    Anandan, Mageshwari
    Nutalapati, Venkatramaiah
    Senadi, Gopal Chandru
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (12)
  • [7] An efficient green synthesis of 5H-spiro[benzo[4,5] imidazo[1,2-c] quinazoline-6,3′-indolin]-2′-ones catalyzed by iodine in ionic liquids
    Zhang, Mei-Mei
    Wang, Yue
    Liu, Jian-Quan
    Wang, Xiang-Shan
    HETEROCYCLIC COMMUNICATIONS, 2017, 23 (05) : 385 - 388
  • [8] Rh-Catalyzed Annulation of ortho-C-H Bonds of 2-Arylimidazoles with 1,4,2-Dioxazol-5-ones toward 5-Arylimidazo[1,2-c]quinazolines
    Wu, Xiaopeng
    Sun, Song
    Xu, Shengbo
    Cheng, Jiang
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (06) : 1111 - 1115
  • [9] Iodine-Mediated Domino Oxidative Cyclization: One-Pot Synthesis of 1,3,4-Oxadiazoles via Oxidative Cleavage of C(sp2)-H or C(sp)-H Bond
    Fan, Yuxing
    He, Yongqin
    Liu, Xingxing
    Hu, Ting
    Ma, Haojie
    Yang, Xiaodong
    Luo, Xinliang
    Huang, Guosheng
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (15) : 6820 - 6825
  • [10] Synthesis of benzo[4,5]imidazo[1,2-a]quinoxalines by I2-mediated sp3 C-H amination
    Chen, Wenjun
    Du, Yangxu
    Wang, Manman
    Fang, Yingchao
    Yu, Wenquan
    Chang, Junbiao
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (22) : 3705 - 3708