Iron-Catalyzed [4C+1N] Cyclization of 4-Acetylenic Ketones with Primary Amines: Synthesis of 5-(Aryl)alkylidene-4,5-dihydropyrroles

被引：12
|
作者：
Sun, Bo [1 ,2 ]
Ma, Quan [2 ]
Wang, Yeming [3 ]
Zhao, Yuegang [2 ]
Liao, Peiqiu [1 ]
Bi, Xihe [1 ,4 ]
机构：
[1] NE Normal Univ, Dept Chem, Changchun 130024, Peoples R China
[2] Changchun Univ Chinese Med, Sch Pharmaceut Sci, Changchun 130117, Peoples R China
[3] Jilin Normal Univ, Dept Chem, Siping 136000, Peoples R China
[4] State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 34期
基金：
中国国家自然科学基金;
关键词：
Amines; Cyclization; Iron; Ketones; Nitrogen heterocycles; OXO KETENE DITHIOACETALS; PROPARGYLIC ALCOHOLS; 3+2 CYCLOADDITION; TERMINAL ALKYNES; ALDEHYDES; 2,3-DIHYDROPYRROLES; HYDROAMINATION; HYDROAZIDATION; HETEROCYCLES; DERIVATIVES;
D O I：
10.1002/ejoc.201403097
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An environmentally friendly route to fully substituted 4,5-dihydropyrroles was developed through the iron-catalyzed [4C+1N] cyclization of 4-acetylenic ketones with primary amines in 1,5-pentanediol.
引用
收藏
页码：7552 / 7555
页数：4
相关论文
共 19 条
  • [1] Iron-catalyzed synthesis of polysubstituted pyrroles via [4C+1N] cyclization of 4-acetylenic ketones with primary amines
    Wang, Yeming
    Bi, Xihe
    Li, Dehua
    Liao, Peiqiu
    Wang, Yidong
    Yang, Jin
    Zhang, Qian
    Liu, Qun
    CHEMICAL COMMUNICATIONS, 2011, 47 (02) : 809 - 811
  • [2] Copper-catalyzed C-C coupling and cyclization: Synthesis of benzo [4,5] imidazo[1,2-a] pyridines and benzo[4,5] imidazo[2,1-a] isoquinolines
    Yang, Byeong Woo
    Pham Duy Quang Dao
    Yoon, Nam Sik
    Cho, Chan Sik
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2017, 851 : 136 - 142
  • [3] Copper-Catalyzed Oxidative Cross-Coupling/C-C Bond Cleavage/Cyclization of Aryl Methyl Ketones with 4-Aminocoumarins: Domino Synthesis of Dicoumarin-Fused [1,5]-Diazocines
    Peng, Fei
    Li, Lili
    Liu, Jin
    Chen, Zhiwei
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (08) : 1667 - 1673
  • [4] An Indium(III)-Catalyzed Synthesis of 4,4-Dichloro-1-aryl-N-alkyl-1-yn-3-amines via an Intermolecular C(sp2)-C(sp) Bond Formation
    Malakar, Chandi C.
    Maes, Bert U. W.
    Tehrani, Kourosch Abbaspour
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (18) : 3461 - 3467
  • [5] Magnetic MOF-199-Catalyzed Synthesis of Benzo[4,5]imidazo[1,2-f]phenanthridines and Their Analogues by Tandem C(sp2)-C Coupling and Cyclization Followed by Aromatization
    Kim, Min Jeong
    Lee, Seong Weon
    Dao, Pham Duy Quang
    Cho, Chan Sik
    CHEMISTRYSELECT, 2023, 8 (29):
  • [6] Cyclization of Activated Methylene Isocyanides with MethylN(N),N′-Di(tri)substituted Carbamimidothioate: A Novel Entry for the Synthesis of N,1-Aryl-4-tosyl/ethoxycarbonyl-1 H-imidazol-5-amines
    Dukanya
    Swaroop, Toreshettahally R.
    Rangappa, Shobith
    Rangappa, Kanchugarakoppal S.
    Basappa
    SYNOPEN, 2019, 3 (03): : 71 - 76
  • [7] Synthesis of 5-Aryl-5H-pyrido[2',1':2,3]imidazo[4,5-b]indoles by Domino Pd- and Cu-Catalyzed C-N Coupling Reactions
    Tran Quang Hung
    Nguyen Minh Quan
    Hoang Van Dong
    Trinh Duy Nguyen
    Hoang Le Tuan Anh
    Trieu Quy Hung
    Nguyen Van Tuyen
    Ngo Thi Thuan
    Tuan Thanh Dang
    Langer, Peter
    SYNLETT, 2019, 30 (03) : 303 - 306
  • [8] Microwave-Assisted Iron(III)Chloride Catalyzed One-Pot Michael Addition-Cyclization for the Synthesis of 6H-Chromeno[4',3':4,5] imidazo[1,2-a]pyridine
    Mishra, Mitali
    Mishra, Nilima P.
    Raiguru, Bishnu P.
    Das, Tapaswini
    Mohapatra, Seetaram
    Nayak, Sabita
    Mishra, Deepak R.
    Panda, Jasmine
    Sahoo, Dipak K.
    CHEMISTRYSELECT, 2021, 6 (15): : 3570 - 3575
  • [9] One-Pot Copper-Catalyzed Cascade Bicyclization Strategy for Synthesis of 2-(1H-Indol-1-yl)-4,5-dihydrothiazoles and 2-(1H-Indol-1-yl)thiazol-5-yl Aryl Ketones with Molecular Oxygen as an Oxygen Source
    Xie, Jialin
    Guo, Zhonglin
    Huang, Yuanqiong
    Qu, Yi
    Song, Hongjian
    Song, Haibin
    Liu, Yuxiu
    Wang, Qingmin
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (03) : 490 - 495
  • [10] Palladium(0)-catalyzed Domino C-N Coupling/Hydroamination/C-H Arylation: Efficient Synthesis of Benzothieno[2′,3′:4,5]pyrrolo[1,2-f]phenanthridines
    Salman, Ghazwan Ali
    Ngo Nghia Pham
    Thang Ngoc Ngo
    Ehlers, Peter
    Villinger, Alexander
    Langer, Peter
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (08) : 1402 - 1406
12