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 29 条
  • [11] 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
  • [12] Sodium Hydroxide Catalyzed N-Alkylation of (Hetero) Aromatic Primary Amines and N1,C5-Dialkylation of 4-Phenyl-2-aminothiazoles with Benzyl Alcohols
    Donthiri, Ramachandra Reddy
    Pappula, Venkatanarayana
    Mohan, Darapaneni Chandra
    Gaywala, Hiren H.
    Adimurthy, Subbarayappa
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (13): : 6775 - 6781
  • [13] 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):
  • [14] Anions Containing Tripoid Conjugated N4- System: Salts of 5-(Substituted Amino)-[1,2,3]triazolo[4,5-c][1,2,5]oxadiazol-5-ium-4-ides, as well as Their Synthesis, Structure, and Thermal Stability
    Voronin, Alexey A.
    Balabanova, Sofya P.
    Fedyanin, Ivan, V
    Churakov, Aleksandr M.
    Pivkina, Alla N.
    Strelenko, Yurii A.
    Klenov, Michael S.
    Tartakovsky, Vladimir A.
    MOLECULES, 2022, 27 (19):
  • [15] Regioselective Synthesis of 4,5-Diaryl-1-methyl-1H-imidazoles Including Highly Cytotoxic Derivatives by Pd-Catalyzed Direct C-5 Arylation of 1-Methyl-1H-imidazole with Aryl Bromides
    Bellina, Fabio
    Cauteruccio, Silvia
    Di Fiore, Annarita
    Rossi, Renzo
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (32) : 5436 - 5445
  • [16] 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
  • [17] A copper-catalyzed synthesis of benzo[4,5]imidazo[1,2-a]pyridine derivatives via C-N bond formation of 2-aminopyridines with arylboronic acids
    Li, Xiao-Tang
    Han, Chuan-Jie
    Zhang, Zhan-Hui
    RESEARCH ON CHEMICAL INTERMEDIATES, 2025, 51 (04) : 1733 - 1747
  • [18] Application of p-TSA in the one pot synthesis of N-methyl-3-nitro-aryl-benzo[4,5]imidazo[1,2-c]pyrimidin-2-amine
    Jadhav, Amol Maruti
    Kim, Yeong Il
    Lim, Kwon Taek
    Jeong, Yeon Tae
    TETRAHEDRON LETTERS, 2018, 59 (06) : 554 - 557
  • [19] New N-(Aryl)-5-((quinolin-8-yloxy)methyl)-1,3,4-oxa/Thiadiazol-2-amines and 4-Aryl-5-((quinolin-8-yloxy)methyl)-2H-1,2,4-triazole-3(4H)-thiones, Synthesis and Characterization
    Saeed, Aamer
    Abbas, Naeem
    Ibrar, Aliya
    Bolte, Michael
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 (05) : 1357 - 1362
  • [20] Practical synthesis of 5H-pyrido[2',1:2,3]imidazo[4,5-b]indoles by Cu- catalyzed double C-N coupling reactions
    Van Phuc, Ban
    Dinh, Quang Huy
    Chi, Nguyen Linh
    Nguyen, Quyet Tien
    Van Tuyen, Nguyen
    Nguyen, Hien
    Langer, Peter
    Dang, Tuan Thanh
    Hung, Tran Quang
    TETRAHEDRON, 2023, 136
123