Base-Promoted Synthesis of Isoquinolines through a Tandem Reaction of 2-Methyl-arylaldehydes and Nitriles

被引:1
|
作者
Shuai, Sujuan [1 ,2 ,4 ]
Mao, Jianyou [3 ]
Zhou, Fan [1 ,2 ,4 ]
Yan, Qifeng [1 ,2 ]
Chen, Lingfeng [1 ]
Li, Jie [1 ,2 ]
Walsh, Patrick J. [5 ]
Liang, Guang [1 ]
机构
[1] Hangzhou Med Coll, Sch Pharmaceut Sci, Hangzhou 311399, Zhejiang, Peoples R China
[2] Zhejiang Univ City Coll, Sch Med, Dept Pharm, Hangzhou 310015, Peoples R China
[3] Nanjing Tech Univ, Inst Adv Synth, Jiangsu Natl Synerget Innovat Ctr Adv Mat, Sch Chem & Mol Engn, Nanjing 211816, Peoples R China
[4] Zhejiang Univ, Coll Pharmaceut Sci, Hangzhou 310058, Peoples R China
[5] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA
来源
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 10期
基金
美国国家科学基金会;
关键词
IRIDIUM COMPLEXES; BETA-PHENYLETHYLAMINES; EFFICIENT SYNTHESIS; DERIVATIVES; FUNCTIONALIZATION; CYCLIZATION; ALLYLATION; ANNULATION; ALDEHYDES; INDOLES;
D O I
10.1021/acs.joc.4c00123
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient method for preparing 3-aryl isoquinolines via a base-promoted tandem reaction is presented. Simply combining commercially available 2-methyl-arylaldehydes, benzonitriles, NaN(SiMe3)(2), and Cs2CO3 enabled the synthesis of a variety of isoquinolines (23 examples, <= 90% yield). Among the syntheses of isoquinolines, the transition metal-free method described here is straightforward, practical, and operationally simple.
引用
收藏
页码:6793 / 6797
页数:5
相关论文
共 50 条
  • [1] Base-promoted tandem synthesis of 2-azaaryl indoline
    Chen, Shuguang
    Tan, Jiahong
    Wu, Hao
    Zhao, Quansheng
    Shang, Yongjia
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (46) : 9133 - 9137
  • [2] Base-Promoted Tandem Synthesis of 2-Azaaryl Tetrahydroquinolines
    Chen, Shuguang
    Yang, Langxuan
    Shang, Yongjia
    Mao, Jianyou
    Walsh, Patrick J.
    ORGANIC LETTERS, 2021, 23 (05) : 1594 - 1599
  • [3] Base-Promoted Tandem Synthesis of 3,4-Dihydroisoquinolones
    Li, Jie
    Wang, Huan
    Jin, Huimin
    Xiang, Zhenhua
    Chen, Lingfeng
    Walsh, Patrick J.
    Liang, Guang
    ORGANIC LETTERS, 2022, 24 (44) : 8125 - 8129
  • [4] Concise Synthesis of (±)-Aurantioclavine through a Base-Promoted Pictet-Spengler Reaction
    Yamada, Koji
    Namerikawa, Yuichi
    Haruyama, Tomohiro
    Miwa, Yoshihisa
    Yanada, Reiko
    Ishikura, Minoru
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (33) : 5752 - 5759
  • [5] Base-Promoted Tandem Synthesis of 6-H-Phenanthridine and its Derivatives
    Jin, Haoyu
    Zeng, Min
    Wang, Shouliang
    Ding, Yitian
    Chen, Suyang
    Feng, Jinxi
    Chen, Xianhao
    Miao, Tingting
    Wu, Fen
    Shi, Qian
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 28 (10)
  • [6] Base-Promoted Tandem Reaction Involving Insertion into Carbon-Carbon σ-Bonds: Synthesis of Xanthone and Chromone Derivatives
    Cheng, Xingcan
    Zhou, Yuanyuan
    Zhang, Fangfang
    Zhu, Kai
    Liu, Yuanyuan
    Li, Yanzhong
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (36) : 12655 - 12659
  • [7] Y Harnessing the reactivity of ortho-formyl-arylketones: base-promoted regiospecific synthesis of functionalized isoquinolines
    Mishra, Pawan K.
    Verma, Shalini
    Kumar, Manoj
    Kumar, Ankit
    Verma, Akhilesh K.
    CHEMICAL COMMUNICATIONS, 2019, 55 (57) : 8278 - 8281
  • [8] Synthesis of Chromenoimidazoles, Annulated with an Azaindole Moiety, through a Base-Promoted Domino Reaction of Cyanomethyl Quaternary Salts
    Voskressensky, Leonid G.
    Storozhenko, Olga A.
    Festa, Alexey A.
    Novikov, Roman A.
    Varlamov, Alexey V.
    SYNTHESIS-STUTTGART, 2017, 49 (12): : 2753 - 2760
  • [9] Base-Promoted Tandem Synthesis of 2-Substituted Indoles and N-Fused Polycyclic Indoles
    Zhou, Fan
    Jin, Huimin
    Zhang, Yuanhang
    Li, Jie
    Walsh, Patrick J.
    Lin, Shengzhang
    ORGANIC LETTERS, 2023, 25 (39) : 7132 - 7136
  • [10] Quinazolinone Synthesis through Base-Promoted SNAr Reaction of ortho-Fluorobenzamides with Amides Followed by Cyclization
    Iqbal, Muhammad Asif
    Lu, Le
    Mehmood, Hina
    Khan, Dost Muhammad
    Hua, Ruimao
    ACS OMEGA, 2019, 4 (05): : 8207 - 8213