Microwave-enhanced synthesis of 2,3,6-trisubstituted pyridazines: application to four-step synthesis of gabazine (SR-95531)

被引：14
|
作者：
Gavande, Navnath [1 ]
Johnston, Graham A. R. [2 ]
Hanrahan, Jane R. [1 ]
Chebib, Mary [1 ]
机构：
[1] Univ Sydney, Fac Pharm, Sydney, NSW 2006, Australia
[2] Univ Sydney, Dept Pharmacol, Adrien Albert Lab Med Chem, Sydney, NSW 2006, Australia
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 18期
关键词：
AMINOBUTYRIC-ACID GABA; A ANTAGONISTS; FUNCTIONALIZED; 3-AMINOPYRIDAZINES; ACETYLCHOLINESTERASE INHIBITORS; CARBON NUCLEOPHILES; ORGANIC-SYNTHESIS; RECEPTOR-SITE; DERIVATIVES; AMINOPYRIDAZINES; AGONISTS;
D O I：
10.1039/c0ob00004c
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Microwave-enhanced, highly efficient protocols for the synthesis of synthetically and biologically important 2,3,6-trisubstituted pyridazine architectures have been developed by sequential amination/Suzuki coupling/alkylation reactions. This powerful strategy is an economical and highly chemoselective protocol for the synthesis of diversified pyridazines. The total synthesis of gabazine (SR-95531) has been achieved using a versatile strategy in four steps and 73% overall yield.
引用
收藏
页码：4131 / 4136
页数：6
相关论文
共 50 条
  • [31] Potent new NK1 antagonists from a modified piperidine template: Diastereoselective synthesis of 2,3,6-trisubstituted piperidines.
    Chappie, TA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U767 - U767
  • [32] Cu(II)-Catalyzed Synthesis of 2,3,6-Trisubstituted Pyridines from Saturated Ketone and Alkynones/1,3-Dicarbonyl Compounds
    Zhan, Zhen Z.
    He, Jian P.
    Jiang, Peng B.
    Zhang, Ming M.
    Wang, He S.
    Luo, Nan
    Huang, Guo S.
    CHEMISTRYSELECT, 2021, 6 (17): : 4160 - 4165
  • [33] Substituent-Controlled Electrocyclization of 2,4-Dienones: Synthesis of 2,3,6-Trisubstituted 2H-Pyran-5-carboxylates and Their Transformations
    Peng, Wei
    Hirabaru, Toshiaki
    Kawafuchi, Hiroyuki
    Inokuchi, Tsutomu
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (28) : 5469 - 5474
  • [34] Two-step Synthesis of 1, 2, 6-Trisubstituted Benzimidazoles from 3-Fluoro-4-nitrotoluene
    Zhang, Li-Jie
    Li, Chun-Yu
    Jin, Hua-Qiang
    Zhou, Li
    Song, Jia-Liang
    Sun, Ya-Quan
    Jingxi Huagong/Fine Chemicals, 2018, 35 (03): : 443 - 448
  • [35] Stereoselective Synthesis of 2,3,6-Trisubstituted Tetrahydropyridines via Tf2O-Mediated Grob Fragmentation: Access to Indolizidines (-)-2091 and (-)-223J
    Lemonnier, Gerald
    Charette, Andre B.
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (21): : 7465 - 7467
  • [36] Mannich Bases as Enone Precursors for Water-Mediated Efficient Synthesis of 2,3,6-Trisubstituted Pyridines and 5,6,7,8-Tetrahydroquinolines
    Hanashalshahaby, Essam Hamied Ahmed
    Unaleroglu, Canan
    ACS COMBINATORIAL SCIENCE, 2015, 17 (06) : 374 - 380
  • [37] Microwave assisted one-pot pseudo four-component synthesis of 2,4,6-trisubstituted pyridines using γ-MnO2 nanoparticles
    Mohammadi, Bagher
    MONATSHEFTE FUR CHEMIE, 2016, 147 (11): : 1939 - 1943
  • [38] Microwave assisted one-pot pseudo four-component synthesis of 2,4,6-trisubstituted pyridines using γ-MnO2 nanoparticles
    Bagher Mohammadi
    Monatshefte für Chemie - Chemical Monthly, 2016, 147 : 1939 - 1943
  • [39] Four-Step Synthesis of 3-Allyl-2-(allyloxy)-5-bromoaniline from 2-Allylphenol
    Aparicio, Enrique B.
    Isbel, Stephen R.
    Bugarin, Alejandro
    MOLBANK, 2024, 2024 (01)
  • [40] Synthesis of nonracemic 2,3,6-trisubstituted piperidine derivatives from sugar lactones via tandem Wittig [2+3] cycloaddition reaction. A novel entry to prosopis and cassia alkaloids
    Herdeis, C
    Schiffer, T
    TETRAHEDRON, 1999, 55 (04) : 1043 - 1056
12345