Copper(I)-catalyzed synthesis of isoindolo[1,2-b]quinazoline derivatives via an α-arylation under Pd and ligand free conditions

被引：1
|
作者：
Zhang, Yan [1 ]
Liu, Jian-Quan [1 ]
Wang, Xiang-Shan [1 ]
机构：
[1] Jiangsu Normal Univ, Sch Chem & Chem Engn, Jiangsu Key Lab Green Synth Funct Mat, Xuzhou 221116, Jiangsu, Peoples R China
来源：
TETRAHEDRON LETTERS | 2020年 / 61卷 / 46期
关键词：
Isoindoloquinazoline; alpha-Arylation reaction; CuI; Pd-free; NUCLEOPHILIC AROMATIC-SUBSTITUTION; EFFICIENT SYNTHESIS; HIGHLY EFFICIENT; QUINAZOLINONES; ANNULATION; HYDROAMINATION; ISOCYANIDE; COMPLEXES; BROMIDES; DESIGN;
D O I：
10.1016/j.tetlet.2020.152508
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A tandem cyclization reaction of diethyl 2-(2-aminobenzamido)malonates and 2-bromobenzaldehydes was developed for the synthesis of isoindolo[1,2-b]quinazoline derivatives. The quinazoline was formed first catalyzed by CuI, followed by a noteworthy alpha-arylation reaction under Pd and ligand-free conditions in the presence of Cs2CO3. (C) 2020 Elsevier Ltd. All rights reserved.
引用
收藏
页数：4
相关论文
共 50 条
  • [1] Synthesis of Indolo[1,2-b]indazole Derivatives via Copper(I)-Catalyzed Intramolecular Amination Reaction
    Chi, Jianwen
    Hang, Chenchen
    Zhu, Yongming
    Katayama, Hajime
    SYNTHETIC COMMUNICATIONS, 2010, 40 (08) : 1123 - 1133
  • [2] Copper(I)-catalyzed synthesis of thienopyrazoloquinazolinone derivatives under ligand-free conditions
    Wen-Ting Zhang
    Dong-Sheng Chen
    Mei-Mei Zhang
    Xiang-Shan Wang
    Research on Chemical Intermediates, 2016, 42 : 6769 - 6776
  • [3] Copper(I)-catalyzed synthesis of thienopyrazolo-quinazolinone derivatives under ligand-free conditions
    Zhang, Wen-Ting
    Chen, Dong-Sheng
    Zhang, Mei-Mei
    Wang, Xiang-Shan
    RESEARCH ON CHEMICAL INTERMEDIATES, 2016, 42 (08) : 6769 - 6776
  • [4] 5H-ISOINDOLO[1,2-B][3]BENZAZEPINES .8. SYNTHESIS OF DERIVATIVES OF 5H-ISOINDOLO[1,2-B]ISOQUINOL-5-ONE
    PROKSA, B
    UHRIN, D
    VADKERTI, A
    CHEMICAL PAPERS, 1991, 45 (04): : 567 - 573
  • [5] Iodine-catalyzed synthesis of 5H-phthalazino[1,2-b]quinazoline and isoindolo[2,1-a]quinazoline derivatives via a chemoselective reaction of 2-aminobenzohydrazide and 2-formylbenzoic acid in ionic liquids
    Jin, Rong-Zhang
    Zhang, Wen-Ting
    Zhou, Yu-Jing
    Wang, Xiang-Shan
    TETRAHEDRON LETTERS, 2016, 57 (23) : 2515 - 2519
  • [6] Reigoselective Arylation of Thiazole Derivatives at 5-Position via Pd Catalysis under Ligand-Free Conditions
    Liu, Xiang-Wei
    Shi, Jiang-Ling
    Yan, Jia-Xuan
    Wei, Jiang-Bo
    Peng, Kun
    Dai, Le
    Li, Chen-Guang
    Wang, Bi-Qin
    Shi, Zhang-Jie
    ORGANIC LETTERS, 2013, 15 (22) : 5774 - 5777
  • [7] SYNTHESIS AND PHARMACOLOGICAL EVALUATION OF ISOINDOLO[1,2-B]QUINAZOLINONE AND ISOINDOLO[2,1-A]BENZIMIDAZOLE DERIVATIVES RELATED TO THE ANTITUMOR AGENT BATRACYLIN
    MEEGALLA, SK
    STEVENS, GJ
    MCQUEEN, CA
    CHEN, AY
    YU, C
    LIU, LF
    BARROWS, LR
    LAVOIE, EJ
    JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (20) : 3434 - 3439
  • [8] An Efficient Synthesis of Indeno [1,2-b]pyridine and Benzo[h]quinoline Derivatives Under Solvent-Free Conditions
    Rong, Liangce
    Han, Hongxia
    Jiang, Hong
    Tu, Shujiang
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 46 (03) : 465 - 468
  • [9] Pd-Catalyzed Arylation of 1,2-Amino Alcohol Derivatives via β-Carbon Elimination
    Sau, Miriam
    Pericas, Miquel A.
    Martin, Ruben
    SYNLETT, 2022, 33 (01) : 52 - 56
  • [10] Synthesis of Quinoxaline Derivatives via Copper(I)-Catalyzed Cross-Coupling Reaction of 1,2-Dihalobenzenes with N,N′-Disubstituted Ethane-1,2-diamines under Ligand- and Solvent-Free Conditions
    Shen, Guodong
    Zhao, Lingyu
    Zhao, Xiliang
    Huangfu, Xinlei
    Li, Zhe
    Wang, Rui
    Zhang, Tongxin
    SYNLETT, 2017, 28 (09) : 1111 - 1115
12345