Sequential decarboxylative azide-alkyne cycloaddition and dehydrogenative coupling reactions: one-pot synthesis of polycyclic fused triazoles

被引:8
|
作者
Bharathimohan, Kuppusamy [1 ,2 ]
Ponpandian, Thanasekaran [3 ]
Ahamed, A. Jafar [1 ]
Bhuvanesh, Nattamai [4 ]
机构
[1] Bharathidasan Univ, Jamal Mohamed Coll, PG & Res Dept Chem, Thiruchirapalli 620020, Tamil Nadu, India
[2] Orchid Chem & Pharmaceut Ltd, R&D Ctr, Drug Discovery Res, Madras 600119, Tamil Nadu, India
[3] Inogent Labs Pvt Ltd, API R&D, IDA, Hyderabad 500076, Andhra Pradesh, India
[4] Texas A&M Univ, Dept Chem, Xray Diffract Lab, College Stn, TX 77842 USA
来源
关键词
copper(II) acetate; decarboxylative CuAAC; dehydrogenative coupling; fused triazoles; one-pot synthesis; H BOND FUNCTIONALIZATION; DIRECT ARYLATIONS; PALLADIUM; 1,2,3-TRIAZOLES; ACID; ACTIVATION; THIAZOLES; MECHANISM; INDOLES;
D O I
10.3762/bjoc.10.321
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we describe a one-pot protocol for the synthesis of a novel series of polycyclic triazole derivatives. Transition metal-catalyzed decarboxylative CuAAC and dehydrogenative cross coupling reactions are combined in a single flask and achieved good yields of the respective triazoles (up to 97% yield). This methodology is more convenient to produce the complex polycyclic molecules in a simple way.
引用
收藏
页码:3031 / 3037
页数:7
相关论文
共 50 条
  • [41] Well-defined copper(I) complexes for Click azide-alkyne cycloaddition reactions: one Click beyond
    Diez-Gonzalez, Silvia
    CATALYSIS SCIENCE & TECHNOLOGY, 2011, 1 (02) : 166 - 178
  • [42] Regioselective synthesis of multisubstituted 1,2,3-triazoles: moving beyond the copper-catalyzed azide-alkyne cycloaddition
    Wei, Fang
    Wang, Weiguo
    Ma, Yudao
    Tung, Chen-Ho
    Xu, Zhenghu
    CHEMICAL COMMUNICATIONS, 2016, 52 (99) : 14188 - 14199
  • [43] Modular synthesis of bis- and tris-1,2,3-triazoles by permutable sequential azide-aryne and azide-alkyne cycloadditions
    Yoshida, Suguru
    Nonaka, Takako
    Morita, Takamoto
    Hosoya, Takamitsu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (38) : 7489 - 7493
  • [44] Heterogeneous Gold Nanoparticle-Based Catalysts for the Synthesis of Click-Derived Triazoles via the Azide-Alkyne Cycloaddition Reaction
    Librando, Ivy L.
    Mahmoud, Abdallah G.
    Carabineiro, Sonia A. C.
    Guedes da Silva, M. Fatima C.
    Maldonado-Hodar, Francisco J.
    Geraldes, Carlos F. G. C.
    Pombeiro, Armando J. L.
    CATALYSTS, 2022, 12 (01)
  • [45] One-pot sequential C-N coupling and cross dehydrogenative couplings: synthesis of novel azole fused imidazo[1,2-a]pyridines
    Pericherla, Kasiviswanadharaju
    Khedar, Poonam
    Khungar, Bharti
    Kumar, Anil
    CHEMICAL COMMUNICATIONS, 2013, 49 (28) : 2924 - 2926
  • [46] One-Pot Reactions for Modular Synthesis of Polysubstituted and Fused Pyridines
    Song, Zhidong
    Huang, Xin
    Yi, Wenbin
    Zhang, Wei
    ORGANIC LETTERS, 2016, 18 (21) : 5640 - 5643
  • [47] One-pot Sonogashira coupling, hydroamination of alkyne and intramolecular C-H arylation reactions toward the synthesis of indole-fused benzosultams
    Debnath, Sudarshan
    Mondal, Shovan
    TETRAHEDRON LETTERS, 2018, 59 (23) : 2260 - 2263
  • [48] Polymer anchored ruthenium complex: A highly active and recyclable catalyst for one-pot azide-alkyne cycloaddition and transfer-hydrogenation of ketones under mild conditions
    Molla, Rostam Ali
    Roy, Anupam Singha
    Ghosh, Kajari
    Salam, Noor
    Iqubal, Md Asif
    Tuhina, K.
    Islam, Sk Manirul
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2015, 776 : 170 - 179
  • [49] One-Pot Sequential N-Heterocyclic Carbene/Rhodium(III) Catalysis: Synthesis of Fused Polycyclic Isocoumarins
    Youn, So Won
    Yoo, Huen Ji
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (13) : 2176 - 2183
  • [50] Development of a one-pot sequential Sonogashira coupling for the synthesis of benzofurans
    Csekei, Marton
    Novak, Zoltan
    Kotschy, Andras
    TETRAHEDRON, 2008, 64 (37) : 8992 - 8996