Thermal 1,3-dipolar cycloaddition of azomethine imines with alkynes affording N,N-bicyclic pyrazolidinones under microwave irradiation

被引：20
|
作者：
Yang, Zhi-Wei [1 ]
Wang, Jing-Fang [1 ]
Peng, Li-Jie [1 ]
You, Xiao-Lin [1 ]
Cui, Hai-Lei [1 ]
机构：
[1] Chongqing Univ Arts & Sci, Int Acad Targeted Therapeut & Innovat, 319 Honghe Ave, Chongqing 402160, Peoples R China
来源：
TETRAHEDRON LETTERS | 2016年 / 57卷 / 47期
基金：
美国国家科学基金会;
关键词：
1,3-Dipolar cycloaddition; Microwave; Internal alkynes; Azomethine imines; N; N-Bicyclic pyrazolidinones; CATALYZED 3+2 CYCLOADDITION; ASSISTED ORGANIC-SYNTHESIS; HETEROCYCLES; ANNULATIONS; DERIVATIVES; ALLENOATES; CHEMISTRY; YLIDES;
D O I：
10.1016/j.tetlet.2016.10.030
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A metal and catalyst free 1,3-dipolar cycloaddition reaction of azomethine imines with internal alkynes has been developed. Various N,N-bicyclic pyrazolidinones could be prepared quickly under microwave irradiation in moderate to excellent yields (up to 96%). A wide range of azomethine imines and electron-deficient internal alkynes were applicable to this reaction. In addition, gram-scale reaction could be achieved and fully substituted pyrazole can be obtained by easy transformation of N,N-bicyclic pyrazolidinone. This environment friendly dipolar cycloaddition is remarkable for its simplicity in conditions and wide structural diversity. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5219 / 5222
页数：4
相关论文
共 50 条
  • [1] Enantioselective 1,3-dipolar cycloaddition of methyleneindolinones and N, N′-cyclic azomethine imines
    Hong, Liang
    Kai, Ming
    Wu, Chongyang
    Sun, Wangsheng
    Zhu, Gongming
    Li, Guofeng
    Yao, Xiaojun
    Wang, Rui
    CHEMICAL COMMUNICATIONS, 2013, 49 (60) : 6713 - 6715
  • [2] Diastereoselective 1,3-Dipolar Cycloadditions of N,N′-Cyclic Azomethine Imines with Iminooxindoles for Access to Oxindole Spiro-N,N-bicyclic Heterocycles
    Zhao, Hong-Wu
    Li, Bo
    Pang, Hai-Liang
    Tian, Ting
    Chen, Xiao-Qin
    Song, Xiu-Qing
    Meng, Wei
    Yang, Zhao
    Zhao, Yu-Di
    Liu, Yue-Yang
    ORGANIC LETTERS, 2016, 18 (04) : 848 - 851
  • [3] Copper-catalyzed 1,3-dipolar cycloaddition of methyleneindolinones and N,N'-cyclic azomethine imines
    Di Zhang
    Da-Ming Zhang
    Guang-Yang Xu
    Jiang-Tao Sun
    Chinese Chemical Letters, 2015, (03) : 301 - 303
  • [4] Copper-catalyzed 1,3-dipolar cycloaddition of methyleneindolinones and N,N′-cyclic azomethine imines
    Zhang, Di
    Zhang, Da-Ming
    Xu, Guang-Yang
    Sun, Jiang-Tao
    CHINESE CHEMICAL LETTERS, 2015, 26 (03) : 301 - 303
  • [5] Chiral NHC-catalyzed 1,3-dipolar [3+2] cycloaddition of azomethine imines with α-chloroaldehydes for the synthesis of bicyclic pyrazolidinones
    Yang, Limin
    Lv, Yunbo
    Wang, Fei
    Zhong, Guofu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (24) : 4433 - 4438
  • [6] Thermal 1,3-dipolar cycloaddition reaction of azomethine imines with active esters
    He, Liwenze
    Liu, Lin
    Han, Runfeng
    Zhang, Weiwei
    Xie, Xingang
    She, Xuegong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (28) : 6757 - 6761
  • [7] 1,3-Dipolar cycloaddition reactions of azomethine ylides and alkynes
    Gulevskaya, Anna V.
    Nelina-Nemtseva, Julia I.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2018, 54 (12) : 1084 - 1107
  • [8] 1,3-Dipolar cycloaddition reactions of azomethine ylides and alkynes
    Anna V. Gulevskaya
    Julia I. Nelina-Nemtseva
    Chemistry of Heterocyclic Compounds, 2018, 54 : 1084 - 1107
  • [9] An Efficient Copper-mediated 1,3-Dipolar Cycloaddition of Pyrazolidinone-based Dipoles to Terminal Alkynes to Produce N,N-Bicyclic Pyrazolidinone Derivatives
    Oishi, Takamichi
    Yoshimura, Kazuaki
    Yamaguchi, Kazuya
    Mizuno, Noritaka
    CHEMISTRY LETTERS, 2010, 39 (10) : 1086 - 1087
  • [10] Organocatalytic Asymmetric Inverse-Electron-Demand 1,3-Dipolar Cycloaddition of N,N′-Cyclic Azomethine Imines
    Zhu, Ren-Yi
    Wang, Cong-Shuai
    Zheng, Jian
    Shi, Feng
    Tu, Shu-Jiang
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (19): : 9305 - 9312
12345