Cationic Pd(II) catalyzed regioselective intramolecular hydroarylation for the efficient synthesis of 4-aryl-2-quinolones

被引:21
|
作者
Singh, Karandeep [1 ,2 ]
Malviya, Bhanwar Kumar [1 ]
Verma, Ved Prakash [3 ]
Badsara, Satpal Singh [4 ]
Bhardwaj, Vimal K. [5 ]
Sharma, Siddharth [1 ]
机构
[1] Mohanlal Sukhadia Univ, Dept Chem, Udaipur 313001, Rajasthan, India
[2] Guru Nanak Dev Univ, UGC Ctr Advance Studies Chem, Dept Chem, Amritsar 143005, Punjab, India
[3] Banasthali Univ, Dept Chem, Newai Jodhpuriya Rd, Vanasthali 304022, India
[4] Univ Rajasthan, Ctr Adv Study, Dept Chem, MFOS Lab, JLN Marg, Jaipur 302004, Rajasthan, India
[5] Natl Inst Technol Jalandhar, Dept Chem, Jalandhar 144011, Punjab, India
关键词
Multi-component reaction; Ugi reaction; Isocyanide; Hydroarylation; Cyclization; Palladium catalyst; BIOAVAILABLE OXYTOCIN ANTAGONISTS; ONE-POT; MULTICOMPONENT REACTION; COMBINATORIAL SYNTHESIS; CASCADE REACTION; BETA-LACTAMS; METAL-FREE; DERIVATIVES; CYCLIZATION; 2,5-DIKETOPIPERAZINES;
D O I
10.1016/j.tet.2019.03.026
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A divergent regioselective palladium (II) catalyzed approach through post Ugi cyclization is described. The Ugi adduct underwent intramolecular ortho-hydroarylation via 6-endo-dig cyclization for the direct access to 4-aryl-2-quinolones. Incorporation of iodine at the C-3 position of 2-quinolone followed by Suzuki-Miyaura coupling results into the more diversified 3,4-diaryl-2-quinolones. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2506 / 2520
页数:15
相关论文
共 50 条
  • [41] A palladium-catalyzed intramolecular carbonylative annulation reaction for the synthesis of 4,5-fused tricyclic 2-quinolones
    Zhang, Xiwu
    Liu, Haichao
    Jia, Yanxing
    CHEMICAL COMMUNICATIONS, 2016, 52 (49) : 7665 - 7667
  • [42] Total synthesis of SS20846A via intramolecular Pd(II)-catalyzed cyclization
    Yokoyama, H
    Otaya, K
    Yamaguchi, S
    Hirai, Y
    TETRAHEDRON LETTERS, 1998, 39 (33) : 5971 - 5974
  • [43] Silver-catalyzed intramolecular hydroamination of alkynes in aqueous media: efficient and regioselective synthesis for fused benzimidazoles
    Zhang, Xu
    Zhou, Yu
    Wang, Hengshuai
    Guo, Diliang
    Ye, Deju
    Xu, Yungen
    Jiang, Hualiang
    Liu, Hong
    GREEN CHEMISTRY, 2011, 13 (02) : 397 - 405
  • [44] Asymmetric Synthesis of 2-Aryl-2,3-dihydro-4-quinolones via Bifunctional Thiourea-Mediated Intramolecular Cyclization
    Liu, Xiaoqian
    Lu, Yixin
    ORGANIC LETTERS, 2010, 12 (23) : 5592 - 5595
  • [45] Efficient Pd-Catalyzed Allene Synthesis from Alkynes and Aryl Bromides through an Intramolecular Base-Assisted Deprotonation (iBAD) Mechanism
    Nella, Natalie
    Parker, Evelyne
    Hitce, Julien
    Larini, Paolo
    Jazzar, Rodolphe
    Baudoin, Olivier
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (41) : 13272 - 13278
  • [46] Synthesis of 4-Aryl-2(5H)-furanones by Gold(I)-Catalyzed Intramolecular Annulation
    Sun, Haifeng
    Huang, He
    Zhang, Dengyou
    Feng, Enguang
    Qian, Wangke
    Zhang, Lei
    Chen, Kaixian
    Liu, Hong
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (09) : 1413 - 1419
  • [47] Synthesis of tetrahydroquinolines by gold-catalyzed cascade ring-opening-intramolecular hydroarylation of 2-alkynylazetidines
    Kariya, Touya
    Hirokane, Tsukasa
    Yoshida, Masahiro
    TETRAHEDRON, 2024, 150
  • [48] 4-aryl-2-quinolones through a pseudo-domino Heck/Buchwald-Hartwig reaction in a molten tetrabutylammonium acetate/tetrabutylammonium bromide mixture
    Battistuzzi, Gianfranco
    Bernini, Roberta
    Cacchi, Sandro
    De Salve, Ilse
    Fabrizi, Giancarlo
    ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (03) : 297 - 302
  • [49] Pd-catalysed intramolecular regioselective arylation of 2-pyrones, pyridones, coumarins and quinolones by C-H bond functionalization
    Nolan, Marie-Therese
    Bray, Joshua T. W.
    Eccles, Kevin
    Cheung, Man Sing
    Lin, Zhenyang
    Lawrence, Simon E.
    Whitwood, Adrian C.
    Fairlamb, Ian J. S.
    McGlacken, Gerard P.
    TETRAHEDRON, 2014, 70 (40) : 7120 - 7127
  • [50] Pd-catalyzed intramolecular Heck reaction for the synthesis of 2-methylbenzofurans
    Zhou, Lixin
    Shi, Yuxing
    Zhu, Xueyan
    Zhang, Peng
    TETRAHEDRON LETTERS, 2019, 60 (30) : 2005 - 2008