An expedient ruthenium(<sc>ii</sc>) catalyzed multicomponent access to phthalazinones bearing trisubstituted alkenes

被引:0
|
作者
Sekar, Manikandan [1 ]
Sreedharan, Ramdas [1 ]
Premkumar, Egambaram [1 ]
Purushothaman, Rajeshwaran [1 ]
Gandhi, Thirumanavelan [1 ]
机构
[1] Vellore Inst Technol Vellore, Sch Adv Sci, Dept Chem, Vellore 632014, Tamil Nadu, India
关键词
OLEFINS; ALKYNES;
D O I
10.1039/d4ob01890g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nitrogen based heterocycles bearing trisubstituted alkenes are prodigious and indispensable motifs in pharmaceuticals, clinical candidates and functional materials. Herein, we developed a tandem one-pot ruthenium-catalyzed multicomponent reaction to access phthalazinones bearing trisubstituted alkenes by employing readily available hydrazines, 2-formyl-benzoic acid and alkynes. The key highlights of this work are its atom economy and greenness, with water as the only byproduct. This reaction exhibits high functional group tolerance and is also scalable to gram-scale synthesis. Remarkably, the current protocol is applied to a four-component reaction involving in situ nitro reduction by utilizing TFE (2,2,2-trifluoroethanol) as a liquid hydrogen carrier, along with imine formation and esterification. A series of control experiments were conducted to elucidate the reaction mechanism. Importantly, the possible intermediates were confirmed by mass spectrometry. Moreover, the products obtained show strong emission properties that are aligning well with DFT calculations.
引用
收藏
页码:2411 / 2417
页数:7
相关论文
共 50 条
  • [1] Palladium(<sc>ii</sc>)-catalyzed enantioselective desymmetrization ring opening of oxabicyclic alkenes with alkynylanilines: efficient access to enantioenriched functionalized cyclohexenes
    Tan, Binhong
    Meng, Junjie
    Liu, Qianru
    Chen, Shixin
    Xue, Mingyue
    Zhang, Yue
    Zhang, Yuping
    Li, Zhaodong
    ORGANIC CHEMISTRY FRONTIERS, 2025,
  • [2] Visible light-induced ruthenium(<sc>ii</sc>)-catalyzed hydroarylation of unactivated olefins
    Trienes, Sven
    Golling, Stephane
    Gieuw, Matthew H.
    Di Matteo, Marco
    Ackermann, Lutz
    CHEMICAL SCIENCE, 2024, 15 (45) : 19037 - 19043
  • [3] Ruthenium(<sc>ii</sc>) complexes with photoswitchable and photoejectable ligands
    Sarma, Kavisha A.
    Middleton, Isis A.
    Chak, Man Him
    Violi, Jake P.
    Bhadbhade, Mohan
    Donald, William A.
    Beves, Jonathon E.
    DALTON TRANSACTIONS, 2025, 54 (12) : 4871 - 4875
  • [4] Dearomatized diimines for nickel(<sc>ii</sc>) and palladium(<sc>ii</sc>) catalyzed ethylene polymerization and copolymerization
    Guo, Lihua
    Zhao, Wei
    Ji, Mingjun
    Chen, Weiqiang
    Li, Pengwei
    Li, Lijie
    Li, Jiaxing
    Liu, Zhe
    INORGANIC CHEMISTRY FRONTIERS, 2024, 11 (05) : 1394 - 1412
  • [5] Cobalt(II)-Catalyzed Stereoselective Olefin Isomerization: Facile Access to Acyclic Trisubstituted Alkenes
    Zhang, Sheng
    Bedi, Deepika
    Cheng, Lu
    Unruh, Daniel K.
    Li, Guigen
    Findlater, Michael
    Journal of the American Chemical Society, 2020, 142 (19): : 8910 - 8917
  • [6] Cobalt(II)-Catalyzed Stereoselective Olefin Isomerization: Facile Access to Acyclic Trisubstituted Alkenes
    Zhang, Sheng
    Bedi, Deepika
    Cheng, Lu
    Unruh, Daniel K.
    Li, Guigen
    Findlater, Michael
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (19) : 8910 - 8917
  • [7] Ru(<sc>ii</sc>)-catalyzed cascade cis carbohalogenation and cyclization of alkyne-tethered cyclohexadienones for synthesizing tetrasubstituted alkenes
    Huang, Xiaoli
    Yi, Cui
    Xiong, Ruji
    Bai, Meiqi
    Tang, Yuhai
    Xu, Silong
    Li, Yang
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (09) : 2572 - 2578
  • [8] Ni(<sc>ii</sc>)-catalyzed nucleophilic substitution for the synthesis of allenylselenide
    Zeng, Ling-Hong
    Cui, Ranran
    Huang, Zhuo
    Zhang, Qing-Wei
    CHEMICAL COMMUNICATIONS, 2025, 61 (06) : 1192 - 1195
  • [9] (NHC)Ni(<sc>ii</sc>)-catalyzed regioselective hydroalkenylation of norbornene derivatives: fine-tuning of NHC ligands and donor alkenes
    Yu, Meng
    Gu, Xiao
    Ho, Chun-Yu
    CHEMICAL COMMUNICATIONS, 2024, 60 (76) : 10508 - 10511
  • [10] Ni(<sc>ii</sc>)-catalyzed enantioselective α-hydrazination of α-fluoroesters: access to chiral quaternary α-fluorinated α-amino acid derivatives
    Yang, Wei-Jing
    Zhang, Jun-Hao
    Li, Ning
    Xie, Ming-Sheng
    Guo, Hai-Ming
    ORGANIC CHEMISTRY FRONTIERS, 2025, 12 (08): : 2746 - 2751