Late-stage diversification of biologically active pyridazinones via a direct C-H functionalization strategy

被引:6
|
作者
Li, Wei [1 ]
Fan, Zhoulong [2 ,3 ]
Geng, Kaijun [2 ,3 ]
Xu, Youjun [1 ]
Zhang, Ao [2 ,3 ]
机构
[1] Shenyang Pharmaceut Univ, Sch Pharmaceut Engn, Shenyang 110016, Peoples R China
[2] Chinese Acad Sci, SIMM, CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China
[3] Chinese Acad Sci, SIMM, SOMCL, Shanghai 201203, Peoples R China
关键词
CATALYZED DIRECT ARYLATION; STAPHYLOCOCCUS-AUREUS; MULTIKILOGRAM SYNTHESIS; COUPLING REACTIONS; INTERNAL ALKYNES; BOND FORMATION; ACTIVATION; OXIDATION; VERSATILE; ACCESS;
D O I
10.1039/c4ob02061h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Divergent C-H functionalization reactions (arylation, carboxylation, olefination, thiolation, acetoxylation, halogenation, naphthylation) using a pyridazinone moiety as an internal directing group were successfully established. This approach offers a late-stage, ortho-selective diversification of a biologically active pyridazinone scaffold. Seven series of novel pyridazinone analogues were synthesized conveniently as the synthetic precursors of potential sortase A (SrtA) inhibitors.
引用
收藏
页码:539 / 548
页数:10
相关论文
共 50 条
  • [31] Electrochemical C-H phosphorylation of arenes in continuous flow suitable for late-stage functionalization
    Long, Hao
    Huang, Chong
    Zheng, Yun-Tao
    Li, Zhao-Yu
    Jie, Liang-Hua
    Song, Jinshuai
    Zhu, Shaobin
    Xu, Hai-Chao
    NATURE COMMUNICATIONS, 2021, 12 (01)
  • [32] Characterization of MalA, an iterative halogenase for late-stage C-H functionalization of indole alkaloids
    Fraley, Amy
    Tran, Hong
    Dan, Qingyun
    Mercado, Eduardo
    Li, Shengying
    Smith, Janet
    Sarpong, Richmond
    Williams, Robert
    Sherman, David
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
  • [33] Late-Stage C-H Functionalization of Nicotinamides for the Expedient Discovery of Novel Antifungal Leads
    Wang, Guotong
    Cui, Pengcheng
    Bai, Hongjin
    Wei, Sanyue
    Li, Shengkun
    JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2019, 67 (43) : 11901 - 11910
  • [34] Mechanistic insights into Fe catalyzed late-stage functionalization of amine C-H bonds
    Emmert, Marion
    Legacy, Christopher
    Frenette, Mathieu
    Greenaway, Frederick
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
  • [35] Late-Stage Functionalization of the Periphery of Oligophenylene Dendrimers with Various Arene Units via Fourfold C-H Borylation
    Masuda, Ryosuke
    Kuwano, Satoru
    Goto, Kei
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (21): : 14433 - 14443
  • [36] SYNTHESIS OF A NEW OSELTAMIVIR DERIVATIVE THROUGH LATE-STAGE CATALYTIC C-H FUNCTIONALIZATION
    Saito, Kenta
    Kanai, Motomu
    HETEROCYCLES, 2012, 86 (02) : 1565 - 1574
  • [37] Late stage C-H functionalization via chalcogen and pnictogen salts
    Kelly, Christopher B.
    Padilla-Salinas, Rosaura
    CHEMICAL SCIENCE, 2020, 11 (37) : 10047 - 10060
  • [38] Selective C-H fluorination of pyridines and diazines: Development and applications to late-stage functionalization
    Fier, Patrick S.
    Hartwig, John F.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [39] Programmable late-stage C-H bond functionalization enabled by integration of enzymes with chemocatalysis
    Craven, Elliott J.
    Latham, Jonathan
    Shepherd, Sarah A.
    Khan, Imtiaz
    Diaz-Rodriguez, Alba
    Greaney, Michael F.
    Micklefield, Jason
    NATURE CATALYSIS, 2021, 4 (05) : 385 - 394
  • [40] C-H bond activation enables the rapid construction and late-stage diversification of functional molecules
    Wencel-Delord, Joanna
    Glorius, Frank
    NATURE CHEMISTRY, 2013, 5 (05) : 369 - 375