A Facile Synthesis of CF3-Substituted Pyrazolidines and Pyrazolines

被引:17
|
作者
Liu, Lili [1 ]
Huang, Danfeng [1 ]
Wang, Yuxiang [1 ]
Wen, Lan [1 ]
Yang, Zheng [1 ]
Su, Yingpeng [1 ]
Wang, Kehu [1 ]
Hu, Yulai [1 ]
机构
[1] Northwest Normal Univ, Coll Chem & Chem Engn, Lanzhou 730070, Gansu, Peoples R China
基金
中国国家自然科学基金;
关键词
trifluoromethyl building blocks; cycloaddition; trifluoromethylated N-acylhydrazones; alkenes; trifluoromethyl pyrazolidines; trifluoromethyl pyrazolines; SILICON LEWIS-ACID; ENANTIOSELECTIVE FLUORINATION; LOCAL-ANESTHETICS; AZOMETHINE IMINES; DERIVATIVES; TRIFLUOROMETHYLATION; ANTIDEPRESSANT; CYCLOADDITION; HYDRAZONES; KETONES;
D O I
10.6023/cjoc201712036
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Lewis acid-catalyzed [3+2] cycloaddition of trifluoromethylated N-acylhydrazones with alkenes was explored, and a series of CF3-substituted pryazolidines were obtained in high yields (up to 91%). The reaction features the use of cheap and readily available trifluoromethylated N-acylhydrazones as trifluoromethyl building blocks, mild reaction conditions and easy operation. Furthermore, the cycloadducts can be transformed into trifluoromethylated pyrazolines in excellent yields.
引用
收藏
页码:1469 / 1476
页数:8
相关论文
共 59 条
  • [1] Pyrazolidine derivatives with heteroaryl urea as dipeptidyl peptidase IV inhibitors
    Ahn, JH
    Jung, SH
    Kim, JA
    Song, SB
    Kwon, SJ
    Kim, KR
    Dal Rhee, S
    Park, SD
    Lee, JM
    Kim, SS
    Cheon, HG
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2005, 53 (08) : 1048 - 1050
  • [2] Behr L.C., 1967, Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings, P1
  • [3] Berenson H, 1976, US 3931406, Patent No. 3931406
  • [4] Chen HF, 2011, CHINESE J ORG CHEM, V31, P231
  • [5] Cross B., 1976, US 3948936, Patent No. 3948936
  • [6] Size effects on the optical properties of organic nanoparticles
    Fu, HB
    Yao, JN
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (07) : 1434 - 1439
  • [7] Successful fluorine-containing herbicide agrochemicals
    Fujiwara, Tomoya
    O'Hagan, David
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2014, 167 : 16 - 29
  • [8] Synthesis and Reactivity of Unsymmetrical Azomethine Imines Formed Using Alkene Aminocarbonylation
    Gan, Wei
    Moon, Patrick J.
    Clavette, Christian
    Das Neves, Nicolas
    Markiewicz, Thomas
    Toderian, Amy B.
    Beauchemin, Andre M.
    [J]. ORGANIC LETTERS, 2013, 15 (08) : 1890 - 1893
  • [9] Properties of a new pyrazoline derivative and its application in electroluminescence
    Gao, XC
    Cao, H
    Zhang, LQ
    Zhang, BW
    Cao, Y
    Huang, CH
    [J]. JOURNAL OF MATERIALS CHEMISTRY, 1999, 9 (05) : 1077 - 1080
  • [10] Applications of Fluorine in Medicinal Chemistry
    Gillis, Eric P.
    Eastman, Kyle J.
    Hill, Matthew D.
    Donnelly, David J.
    Meanwell, Nicholas A.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (21) : 8315 - 8359