Synthesis of pertrifluoromethyl pyridazine derivatives via a tandem reaction of aryldiazonium salts with hexafluoroacetylacetone

被引:10
|
作者
Wu, Wei [1 ,2 ]
Han, Xiaoyan [3 ]
Weng, Zhiqiang [1 ,2 ]
机构
[1] Fuzhou Univ, Coll Chem, Key Lab Mol Synth & Funct Discovery, Fuzhou 350108, Peoples R China
[2] Fuzhou Univ, Coll Chem, Fujian Prov Key Lab Electrochem Energy Storage Ma, Fuzhou 350108, Peoples R China
[3] Soochow Univ, Testing & Anal Ctr, Suzhou 215123, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2020年 / 7卷 / 21期
基金
中国国家自然科学基金;
关键词
EFFICIENT SYNTHESIS; FLUORINE; TRIFLUOROMETHYLATION; CHEMISTRY;
D O I
10.1039/d0qo00955e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new strategy for the construction of pertrifluoromethyl pyridazine derivatives is presented. The tandem reaction starts from the condensation of arenediazonium salts with hexafluoroacetylacetone leading to the formation of pertrifluoromethyl pyridazinols, which readily undergo electrophilic substitution reactions with phenols to afford benzo[5,6]chromeno[3,4-c]pyridazine products in the presence of concd H2SO4.
引用
收藏
页码:3499 / 3504
页数:6
相关论文
共 50 条
  • [31] Synthesis of unsymmetrical ketones via dual catalysed cross-coupling of α,β-unsaturated carboxylic acids with aryldiazonium salts
    Chand, Shiv
    Sharma, Anup Kumar
    Pandey, Anand Kumar
    Singh, Krishna Nand
    CHEMICAL COMMUNICATIONS, 2023, 59 (100) : 14827 - 14830
  • [32] Copper-mediated tandem ring-opening/cyclization reactions of cyclopropanols with aryldiazonium salts: synthesis of N-arylpyrazoles
    Liu, Jidan
    Xu, Erjie
    Jiang, Jinyuan
    Huang, Zeng
    Zheng, Liyao
    Liu, Zhao-Qing
    CHEMICAL COMMUNICATIONS, 2020, 56 (14) : 2202 - 2205
  • [33] Synthesis of Tetrahydropyridine Derivatives through a Reaction of 1,6-Enynes, Sulfur Dioxide, and Aryldiazonium Tetrafluoroborates
    An, Yuanyuan
    Wu, Jie
    ORGANIC LETTERS, 2017, 19 (21) : 6028 - 6031
  • [34] Synthesis of hydroxystilbenes and their derivatives via Heck reaction
    Farina, Angela
    Ferranti, Carolina
    Marra, Carolina
    Guiso, Marcella
    Norcia, Giulia
    NATURAL PRODUCT RESEARCH, 2007, 21 (06) : 564 - 573
  • [35] Synthesis of Nitrosobenzene Derivatives via Nitrosodesilylation Reaction
    Kohlmeyer, Corinna
    Klueppel, Maike
    Hilt, Gerhard
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (07): : 3915 - 3920
  • [36] Synthesis of cantharidinimide derivatives via the Mitsunobu reaction
    Lin, PY
    Shi, SJ
    Hsu, FL
    SYNTHETIC COMMUNICATIONS, 1999, 29 (09) : 1611 - 1616
  • [37] Synthesis of Substituted Quinazolin-4(3H)-imines From Aryldiazonium Salts, Nitriles and 2-Cyanoanilines via A Metal-Free Tandem Approach
    Ramanathan, Mani
    Liu, Yi-Hung
    Peng, Shie-Ming
    Liu, Shiuh-Tzung
    ORGANIC LETTERS, 2017, 19 (21) : 5840 - 5843
  • [38] Synthesis of fused tetrazole derivatives via a tandem cycloaddition and N-allylation reaction and parallel synthesis of fused tetrazole amines
    Ek, F
    Manner, S
    Wistrand, LG
    Frejd, T
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (04): : 1346 - 1352
  • [39] Further studies on the reaction of ethyl benzoylacetate with malononitrile: synthesis of some novel pyridine and pyridazine derivatives
    Abdelrazek, FM
    El-Din, AMS
    Mekky, AE
    TETRAHEDRON, 2001, 57 (31) : 6787 - 6791
  • [40] The reaction of β-amino-α,γ-dicyanocrotononitrile with acetophenone: Synthesis of pyridine, pyridazine and thiophene derivatives with antimicrobial activities
    Mohareb, Rafat M.
    El-Sharkawy, Karam A.
    Sherif, Sherif M.
    ACTA PHARMACEUTICA, 2008, 58 (04) : 429 - 444