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 50 条
  • [21] Benzo[1,2-c;4,5-c ']Bis[1,2,5]Thiadiazole in Organic Optoelectronics: A Mini-Review
    Tam, Teck Lip Dexter
    Wu, Jishan
    JOURNAL OF MOLECULAR AND ENGINEERING MATERIALS, 2015, 3 (1-2)
  • [22] 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)
  • [23] Simple inorganic base promoted C-N and C-C formation: synthesis of benzo[4,5]imidazo[1,2-a]pyridines as functional AIEgens used for detecting picric acid
    Yang, Kai
    Luo, Shi-He
    Chen, Si-Hong
    Cao, Xi-Ying
    Zhou, Yong-Jun
    Lin, Yan-Lan
    Huo, Yan-Ping
    Wang, Zhao-Yang
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (37) : 8133 - 8139
  • [24] SYNTHESIS OF SOME 1H,4H-BENZO[4,5]CYCLOHEPTA[1,2-C]PYRAZOL-4-ONE OR 2H,4H-BENZO[4,5]CYCLOHEPTA[1,2-C]PYRAZOL-4-ONE DERIVATIVES
    DESHAYES, C
    CHABANNET, M
    GELIN, S
    HETEROCYCLES, 1983, 20 (08) : 1581 - 1585
  • [25] 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
  • [26] Effective synthesis of 4,5-dibromobenzo[1,2-c:3,4-c']-bis([1,2,5]thiadiazole) by bromination of benzo[1,2-c:3,4-c']-bis([1,2,5]thiadiazole)
    N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave, Moscow
    119991, Russia
    不详
    300350, China
    不详
    300071, China
    不详
    119334, Russia
    Chem. Heterocycl. Compd., 7-8 (403-408): : 403 - 408
  • [27] A new heteroaromatic system -: benzo[4,5]imidazo[1,2-c]pyrido[3′,2′:4,5]-thieno[2,3-e][1,2,3]triazine
    Vasilin, VK
    Kaigorodova, EA
    Lipunov, MM
    Krapivin, GD
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2002, (05): : 713 - 714
  • [28] BENZO[4,5]CYCLOHEPTA[1,2-C]PYRROLE DERIVATIVES VIA INTRAMOLECULAR CYCLOADDITION AND SOLVOLYTIC RING EXPANSION
    COX, MT
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (22) : 903 - 905
  • [29] 1,2,3-BENZOTRIAZINES .3. SYNTHESIS OF PYRIDO[2',2'(3',2') - 4,5]IMIDAZO[1,2-C][1,2,3]BENZOTRIAZINE AND PYRIDO[3',4'(4',3') - 4,5]IMIDAZO[1,2-C][1,2,3]BENZOTRIAZINE
    SPECTOR, RH
    JOULLIE, MM
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1968, 5 (02) : 301 - &
  • [30] Synthesis of benzo[4,5]imidazo[1,2-a]indolo[1,2-c]quinazolines from 2-(2-bromoaryl)indoles and 2-methoxybenzimidazoles under recyclable magnetic MOF-199 catalysis
    Kim, Min Jeong
    Lee, Seong Weon
    Pham Duy Quang Dao
    Cho, Chan Sik
    APPLIED ORGANOMETALLIC CHEMISTRY, 2022, 36 (11)
12345