Microwave assisted synthesis of phenanthridine derivatives via Suzuki coupling and condensation

被引:2
|
作者
Dende, Satheesh Kumar [1 ,2 ,3 ]
Korupolu, Raghu Babu [2 ]
Doddipalla, Raju [1 ]
Leleti, Krishnakanth Reddy [1 ]
机构
[1] GVK Biosci Private Ltd, Med Chem Div, 28A IDA Nacharam, Hyderabad 500076, India
[2] Andhra Univ, Coll Engn A, Dept Engn Chem, Visakhapatnam 530003, Andhra Pradesh, India
[3] Sai Life Sci Ltd, Med Chem Div, DS-7,ICICI Knowledge Pk, Hyderabad 500078, India
关键词
Phenanthridines; Tosylhydrazones; 2 '-aminophenylboronic acid pinacol esters; Suzuki coupling; Condensation reaction; One pot synthesis; N-TOSYLHYDRAZONES; EXPEDITIOUS SYNTHESIS; CASCADE; ALDEHYDES; ALKALOIDS; CONSTRUCTION; METALATION; QUINOLINES; SYNTHONS; ANALOGS;
D O I
10.1016/j.rechem.2021.100149
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
One-pot synthesis of phenanthridine derivatives using appropriately substituted aromatic ortho-bromo N-tosylhydrazones and 2'-aminobenzeneboronic acid pinacol esters is described. In the presence of Pd(amphos)Cl-2 catalyst, tosylhydrazone precursors undergo a Suzuki cross-coupling reaction with 2'-aminobenzeneboronic acid pinacol ester derivatives followed by intramolecular condensation to form the corresponding phenanthridines derivatives in one step.
引用
收藏
页数:6
相关论文
共 50 条
  • [1] Synthesis of Phenanthridines and Analogues via Suzuki Coupling and Condensation
    Dhara, Shubhendu
    Ghosh, Munmun
    Ray, Jayanta K.
    [J]. SYNLETT, 2013, 24 (17) : 2263 - 2265
  • [2] Microwave-assisted synthesis of difuran and furan-thiophene via Suzuki coupling
    Lin, YS
    Lin, CY
    Huang, DY
    Tsai, TYR
    [J]. JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2005, 52 (05) : 849 - 852
  • [3] Versatile synthesis of functionalised dibenzothiophenes via Suzuki coupling and microwave-assisted ring closure
    Rodriguez-Aristegui, Sonsoles
    Clapham, Kate M.
    Barrett, Lauren
    Cano, Celine
    Desage-El Murr, Marine
    Griffin, Roger J.
    Hardcastle, Ian R.
    Payne, Sara L.
    Rennison, Tommy
    Richardson, Caroline
    Golding, Bernard T.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (17) : 6066 - 6074
  • [4] Solvent-free, microwave-assisted synthesis of thiophene oligomers via Suzuki coupling
    Melucci, M
    Barbarella, G
    Sotgiu, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25): : 8877 - 8884
  • [5] Microwave-assisted synthesis of phenylpyrimidine derivatives via Suzuki-Miyaura reactions in water
    Le, Yi
    Zhang, Yan
    Wang, Qin
    Rao, Nian
    Li, Dan
    Liu, Li
    Ouyang, Guiping
    Yan, Longjia
    [J]. TETRAHEDRON LETTERS, 2021, 68
  • [6] ORGN 567-Synthesis of phenanthrene derivatives via microwave-promoted Suzuki-Miyaura coupling/aldol condensation cascade reaction
    Heo, Jung-Nyoung
    Kim, Young Ha
    Kim, Bum Tae
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
  • [7] An Efficient and Green Microwave-Assisted Synthesis of Quinoline Derivatives via Knoevengal Condensation
    Tasqeeruddin, Syed
    Asiri, Yahya
    Alsherhri, Jaber Abdullah
    [J]. LETTERS IN ORGANIC CHEMISTRY, 2020, 17 (02) : 157 - 163
  • [8] Synthesis of Phenanthridine Derivatives via Photolysis
    Linsenmeier, Anna M.
    Williams, Craig M.
    Braese, Stefan
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (21): : 9127 - 9132
  • [9] Microwave-Assisted Synthesis of 5-Phenyl-2-hydroxyacetophenone Derivatives by a Green Suzuki Coupling Reaction
    Soares, Pedro
    Fernandes, Carlos
    Chavarria, Daniel
    Borges, Fernanda
    [J]. JOURNAL OF CHEMICAL EDUCATION, 2015, 92 (03) : 575 - 578
  • [10] Synthesis of biaryl-styrene monomers by microwave-assisted Suzuki coupling
    Zayas, Hazit A.
    Bowyer, Michael C.
    Gordon, Christopher P.
    Holdsworth, Clovia I.
    McCluskey, Adam
    [J]. TETRAHEDRON LETTERS, 2009, 50 (43) : 5894 - 5895