Metal-Free Tandem Oxidative Cyclization for the Synthesis of 1,2-Dihydropyridazines and Pyrazoles

被引:15
作者
Cheng, Dongping [1 ]
Shen, Yinqiang [1 ]
Wu, Ziliang [1 ]
Xu, Xiaoliang [2 ]
Yan, Jizhong [1 ]
机构
[1] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Peoples R China
[2] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Peoples R China
关键词
SYNERGISTIC CATALYSIS; ALLYLIC ALCOHOLS; DERIVATIVES; ALKENES; DIAMINATION; GENERATION; STRATEGY;
D O I
10.1021/acs.joc.1c00020
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Mediated by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), a novel oxidative coupling of hydrazones and 1,3-diarylpropenes has been disclosed to generate appealing beta,gamma-unsaturated hydrazones, which further undergo 5-exo-trig or 6-endo-trig cascade cyclization to give the respective 1,2-dihydropyridazines or pyrazoles selectively under metal-free conditions. The mechanisms of the coupling and subsequent cyclization are proposed.
引用
收藏
页码:8563 / 8575
页数:13
相关论文
共 62 条
  • [1] Tri- and Tetrasubstituted Pyrazole Derivates: Regioisomerism Switches Activity from p38MAP Kinase to Important Cancer Kinases
    Abu Thaher, Bassam
    Arnsmann, Martina
    Totzke, Frank
    Ehlert, Jan E.
    Kubbutat, Michael H. G.
    Schaechtele, Christoph
    Zimmermann, Markus O.
    Koch, Pierre
    Boeckler, Frank M.
    Laufer, Stefan A.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (02) : 961 - 965
  • [2] Synergistic catalysis: A powerful synthetic strategy for new reaction development
    Allen, Anna E.
    MacMillan, David W. C.
    [J]. CHEMICAL SCIENCE, 2012, 3 (03) : 633 - 658
  • [3] NONPEPTIDE ANGIOTENSIN-II ANTAGONISTS DERIVED FROM 1H-PYRAZOLE-5-CARBOXYLATES AND 4-ARYL-1H-IMIDAZOLE-5-CARBOXYLATES
    ASHTON, WT
    HUTCHINS, SM
    GREENLEE, WJ
    DOSS, GA
    CHANG, RSL
    LOTTI, VJ
    FAUST, KA
    CHEN, TB
    ZINGARO, GJ
    KIVLIGHN, SD
    SIEGL, PKS
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (23) : 3595 - 3605
  • [4] Design, synthesis and biological evaluation of some pyrazole derivatives as anti-inflammatory-antimicrobial agents
    Bekhit, AA
    Abdel-Aziem, T
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (08) : 1935 - 1945
  • [5] One-Pot Synthesis of 2-Cyano-1,4-diketones: Applications to Synthesis of Cyanosubstituted Furans, Pyrroles, and Dihydropyridazines
    Chan, Chieh-Kai
    Chan, Yi-Ling
    Tsai, Yu-Lin
    Chang, Meng-Yang
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (17) : 8112 - 8120
  • [6] Synthesis of Trifluoroethyl Pyrazolines via Trichloroisocyanuric Acid Promoted Cascade Cyclization/Trifluoromethylation of β,γ-Unsaturated Hydrazones
    Chang, Bingbing
    Su, Yingpeng
    Huang, Danfeng
    Wang, Ke-Hu
    Zhang, Weigang
    Shi, Ya
    Zhang, Xinghu
    Hu, Yulai
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (08) : 4365 - 4374
  • [7] Copper(II) Triflate Catalyzed Allylic Arylation of Allylic Alcohols: Direct and Selective Access to C-Allylanilines
    Chen, Ke
    Chen, Houguang Jeremy
    Wong, Jonathan
    Yang, Jinglei
    Pullarkat, Sumod A.
    [J]. CHEMCATCHEM, 2013, 5 (12) : 3882 - 3888
  • [8] Synthesis of acyloxyl pyrazolines by copper-mediated aminoacyloxylation of unsaturated ketohydrazones
    Chen, Manman
    Qi, Lin
    Chen, Jia-Min
    Ren, Pei-Xing
    Du, Jie
    Wang, Li-Jing
    Li, Wei
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (28) : 5136 - 5143
  • [9] Copper-Catalyzed Diamination of Alkenes of Unsaturated Ketohydrazones with Amines
    Chen, Manman
    Wang, Li-Jing
    Ren, Pei-Xing
    Hou, Xiao-Ying
    Fang, Zhang
    Han, Meng-Nan
    Li, Wei
    [J]. ORGANIC LETTERS, 2018, 20 (03) : 510 - 513
  • [10] Copper(I)-Catalyzed Oxyamination of β,γ-Unsaturated Hydrazones: Synthesis of Dihydropyrazoles
    Chen, Shanshan
    Chen, Wenming
    Chen, Xu
    Chen, Guifang
    Ackermann, Lutz
    Tian, Xu
    [J]. ORGANIC LETTERS, 2019, 21 (19) : 7787 - 7790