Solvent-free 1,3-Dipolar Cycloaddition of Azomethine Imines with Terminal Alkynes Promoted by Calcium Fluoride Under the Ball Milling Condition

被引：9
|
作者：
Chen Xianglong [1 ]
Jia Chunman [1 ,2 ]
Cao Li [1 ]
Zhang Dela [1 ]
Liu Shuixiang [2 ]
Zhang Qi [1 ]
机构：
[1] Hainan Univ, Hainan Prov Key Lab Fine Chem, Haikou 570228, Peoples R China
[2] Hainan Univ, Key Study Ctr Minist Educ Trop Resources Utilizat, Haikou 570228, Peoples R China
来源：
CHEMICAL RESEARCH IN CHINESE UNIVERSITIES | 2015年 / 31卷 / 04期
基金：
中国国家自然科学基金;
关键词：
Ball-milling; 1,3-Dipolar cycloaddition; Click chemistry; Solvent-free reaction; (S)-PROLINE-CONTAINING DIPEPTIDES; MECHANOCHEMISTRY; COPPER; CATALYST;
D O I：
10.1007/s40242-015-4480-0
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A convenient and efficient procedure for the synthesis of N, N-bicyclic pyrazolidinone derivatives has been developed via the reaction of azomethine imines with terminal alkynes under the ball milling condition without solvent, which was promoted by calcium fluoride with a catalyst of copper(I) salt. The cyclization reactions exhibited moderate to high yields.
引用
收藏
页码：543 / 548
页数：6
相关论文
共 50 条
  • [41] Porous calcium hydroxyapatite as an efficient catalyst for synthesis of pyrazolines via 1,3-dipolar cycoloaddition under solvent-free microwave irradiation
    Atir, R
    Mallouk, S
    Bougrin, K
    Soufiaoui, M
    Laghzizil, A
    SYNTHETIC COMMUNICATIONS, 2006, 36 (01) : 111 - 120
  • [42] Ultrasound-promoted regioselective and stereoselective synthesis of novel spiroindanedionepyrrolizidines by multicomponent 1,3-dipolar cycloaddition of azomethine ylides
    Elangovann Chandralekha
    Arumugam Thangamani
    Ramiah Valliappan
    Research on Chemical Intermediates, 2013, 39 : 961 - 972
  • [43] Ultrasound-promoted regioselective and stereoselective synthesis of novel spiroindanedionepyrrolizidines by multicomponent 1,3-dipolar cycloaddition of azomethine ylides
    Chandralekha, Elangovann
    Thangamani, Arumugam
    Valliappan, Ramiah
    RESEARCH ON CHEMICAL INTERMEDIATES, 2013, 39 (03) : 961 - 972
  • [44] Copper(I)-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides with Fluorinated Imines: The Expanded Scope and Mechanism Insights
    Wei, Liang
    Li, Qing-Hua
    Wang, Chun-Jiang
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (19): : 11814 - 11824
  • [45] 1,3-dipolar cycloaddition of azomethine ylides derived from imines and difluorocarbene to alkynes: a new active Pb-mediated approach to 2-fluoropyrrole derivatives
    Novikov, MS
    Khlebnikov, AF
    Sidorina, ES
    Kostikov, RR
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (02): : 231 - 237
  • [46] 1,3-dipolar cycloaddition of azomethine ylides derived from imines and difluorocarbene to alkynes: A new active Pb-mediated approach to 2-fluoropyrrole derivatives
    Novikov, Mikhail S.
    Khlebnikov, Alexander F.
    Sidorina, Elena S.
    Kostikov, Rafael R.
    Journal of the Chemical Society, Perkin Transactions 1, 2000, (02): : 231 - 237
  • [47] Copper(II)-Catalyzed Asymmetric 1,3-Dipolar [3+4] Cycloaddition and Kinetic Resolution of Azomethine Imines with Azoalkenes
    Wei, Liang
    Wang, Zuo-Fei
    Yao, Lu
    Qiu, Guofu
    Tao, Haiyan
    Li, Hua
    Wang, Chun-Jiang
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (24) : 3955 - 3959
  • [48] CATALYTIC ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION OF AZOMETHINE IMINES TO ALLYL ALCOHOL UTILIZING TARTARIC ACID ESTER AS A CHIRAL AUXILIARY
    Tanaka, Katsuyoshi
    Kato, Tomomitsu
    Ukaji, Yutaka
    Inomata, Katsuhiko
    HETEROCYCLES, 2010, 80 (02) : 887 - 893
  • [49] Unprecedented 1,3-dipolar cycloaddition of azomethine ylides derived from difluorcarbene and imines to carbonyl compounds - Synthesis of oxazolidine derivatives
    Novikov, MS
    Khlebnikov, AF
    Krebs, A
    Kostikov, RR
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1998, 1998 (01) : 133 - 137
  • [50] 1,3-DIPOLAR CYCLOADDITION OF IMIDATE YLIDES ON IMINO-ALCOHOLS - SYNTHESIS OF NEW IMIDAZOLONES USING SOLVENT-FREE CONDITIONS
    LERESTIF, JM
    PERROCHEAU, J
    TONNARD, F
    BAZUREAU, JP
    HAMELIN, J
    TETRAHEDRON, 1995, 51 (24) : 6757 - 6774
12345