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
  • [11] Efficient Pd(ii)-catalyzed regioselective ortho-halogenation of arylcyanamides
    Boddapati, S. N. Murthy
    Tamminana, Ramana
    Alam, M. Mujahid
    Gugulothu, Sailaja
    Varala, Ravi
    Bollikolla, Hari Babu
    NEW JOURNAL OF CHEMISTRY, 2021, 45 (37) : 17176 - 17182
  • [12] Sequential In-catalyzed intramolecular hydroarylation and Pd-catalyzed cross-coupling reactions using bromopropargyl aryl ethers and amines
    Alonso-Maranon, Lorena
    Sarandeses, Luis A.
    Montserrat Martinez, M.
    Perez Sestelo, Jose
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (04): : 500 - 505
  • [13] A NEW SYNTHESIS OF 2-ARYL-4-QUINOLONES
    KASAHARA, A
    IZUMI, T
    WATABE, H
    TAKAHASHI, S
    CHEMISTRY & INDUSTRY, 1981, (04) : 121 - 121
  • [14] Gold-catalyzed post-Ugi alkyne hydroarylation for the synthesis of 2-quinolones
    Du, Xiaochen
    Huang, Jianjun
    Nechaev, Anton A.
    Yao, Ruwei
    Gong, Jing
    Van der Eycken, Erik V.
    Pereshivko, Olga P.
    Peshkov, Vsevolod A.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2018, 14 : 2572 - 2579
  • [15] SYNTHESIS OF 4-ARYL-SUBSTITUTED BUTENOLIDES AND PENTENOLIDES BY COPPER-CATALYZED HYDROARYLATION
    Yamamoto, Yoshihiko
    Kirai, Naohiro
    HETEROCYCLES, 2010, 80 (01) : 269 - 279
  • [16] Palladium-Catalyzed Enantioselective Intramolecular Hydroarylation of Alkynes To Form Axially Chiral 4-Aryl 2-Quinolinones
    Shibuya, Tetsuro
    Shibata, Yu
    Noguchi, Keiichi
    Tanaka, Ken
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (17) : 3963 - 3967
  • [17] Ruthenium(II)-Catalyzed Regioselective Synthesis of Allyl Ketones from Alkynes and their Silver(I)-Catalyzed Hydroarylation into γ-Functionalized Ketones
    Zhang, Min
    Jiang, Huanfeng
    Dixneuf, Pierre H.
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (10) : 1488 - 1494
  • [18] A NEW METHOD OF SYNTHESIS OF 2-ARYL-4-QUINOLONES VIA PD-CATALYZED CARBONYLATION OF ORTHO-IODOANILINES AND TERMINAL ARYLACETYLENES
    KALININ, VN
    SHOSTAKOVSKII, MV
    PONOMAREV, AB
    DOKLADY AKADEMII NAUK SSSR, 1991, 317 (06): : 1395 - 1397
  • [19] Efficient Synthesis of 6-Aryl-2-chloronicotinic Acids via Pd Catalyzed Regioselective Suzuki Coupling of 2,6-Dichloronicotinic Acid
    Ma, Mingliang
    Li, Chengwei
    Li, Xiaoyan
    Wen, Ke
    Liu, Yahu A.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (06) : 1847 - 1849
  • [20] Regioselective Synthesis of Diversely Substituted Diazoninones Through a Post-Ugi Gold-Catalyzed Intramolecular Hydroarylation Process
    Li, Zhenghua
    Kumar, Amit
    Vachhani, Dipak D.
    Sharma, Sunil K.
    Parmar, Virinder S.
    Van der Eycken, Erik V.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (10) : 2084 - 2091