Metal-free cascade reactions of aldehydes and primary amines for the synthesis of 1,3,4-trisubstituted pyrroles

被引:8
作者
Gao, Yong [1 ]
Hu, Changfeng [2 ]
Wan, Jie-Ping [1 ]
Wen, Chengping [2 ]
机构
[1] Jiangxi Normal Univ, Coll Chem & Chem Engn, Nanchang 330022, Peoples R China
[2] Zhejiang Chinese Med Univ, Coll Basic Med Sci, Hangzhou 310053, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
Cascade reaction; Metal-free; Oxidation; Polysubstituted; Pyrroles; HIGHLY SUBSTITUTED PYRROLES; ONE-POT SYNTHESIS; POLYSUBSTITUTED PYRROLES; TETRASUBSTITUTED PYRROLES; MULTICOMPONENT REACTIONS; DIVERGENT SYNTHESIS; HERONAPYRROLE C; CONSTRUCTION; ISOCYANIDES; DERIVATIVES;
D O I
10.1016/j.tetlet.2016.09.063
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of 1,3,4-trisubstituted pyrroles has been realized via the cascade reactions of phenylacetaldehydes and primary amines. It is the first time that this annulation involving the construction of one new C-C and two new C-N bonds has been successfully conducted under metal-free conditions. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4854 / 4857
页数:4
相关论文
共 50 条
  • [31] Development of an unexpected reaction pathway for the synthesis of 1,2,4-trisubstituted pyrrolo[1,2-a]quinoxalines through palladium-catalyzed cascade reactions
    Keivanloo, Ali
    Soozani, Atena
    Bakherad, Mohammad
    Mirzaee, Mandi
    Rudbari, Hadi Amiri
    Bruno, Giuseppe
    TETRAHEDRON, 2017, 73 (12) : 1633 - 1639
  • [32] A solvent and transition metal-free, highly efficient Bronsted acidic ionic liquid promoted one-potthree-component reactions for the synthesis of tetrasubstituted pyrroles
    Atar, Amol Balu
    Han, Eunbi
    Sohn, Dae Hyup
    Kang, Jongmin
    SYNTHETIC COMMUNICATIONS, 2019, 49 (09) : 1181 - 1192
  • [33] A new route for the synthesis of 1,3,4-trisubstituted pyrazolo[4,3-c] quinolines via a multicomponent reaction
    Alizadeh, Abdolali
    Moafi, Leila
    Ghanbaripour, Rashid
    Abadi, Marziyeh Hossein
    Zhu, Zhe
    Kubicki, Maciej
    TETRAHEDRON, 2015, 71 (21) : 3495 - 3499
  • [34] Synthesis, characterization, and cytotoxic activity of some new 1,3,4-trisubstituted pyrazoles against diverse tumor cell lines
    Srour, Aladdin M.
    Fahmy, Hoda H.
    Khater, Mai A.
    El-Manawaty, May A.
    Shalaby, ElSayed M.
    MONATSHEFTE FUR CHEMIE, 2018, 149 (06): : 1137 - 1147
  • [35] Metal-Free Synthesis of Pyrimidine and Naphthoquinone-Fused Pyrroles from Arylglyoxal-Based Domino Reactions
    Panday, Anoop Kumar
    Ali, Danish
    Parvin, Tasneem
    Choudhury, Lokman H. H.
    CHEMISTRYSELECT, 2023, 8 (14):
  • [36] Acid-promoted metal-free synthesis of 3-ketoquinolines from amines, enaminones and DMSO
    Jiang, Tao-Shan
    Zhou, Yuhui
    Dai, Long
    Liu, Xiaojun
    Zhang, Xiuli
    TETRAHEDRON LETTERS, 2019, 60 (31) : 2078 - 2083
  • [37] A metal-free cascade reaction of β-halo-α,β-unsaturated aldehydes and 1,4-dithiane-2,5-diols: synthesis of polycyclic 2-formylthiophenes
    Goswami, Limi
    Neog, Kashmiri
    Sharma, Kumud
    Gogoi, Pranjal
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (31) : 6470 - 6473
  • [38] Direct amination of 2-(1-tosylalkyl)phenols with aqueous ammonia: a metal-free synthesis of primary amines
    Wu, Bo
    Gao, Xiang
    Chen, Mu-Wang
    Zhou, Yong-Gui
    TETRAHEDRON LETTERS, 2015, 56 (09) : 1135 - 1137
  • [39] Metal-Free Synthesis of Highly Diversified Pyrazole C-3/4/5 Tethered 1,3,4-Oxadiazoles and Their Photophysical Assessment
    Sharma, Shubham
    Vaishali, Nisha
    Devi, Nisha
    Singh, Virender
    CHEMISTRY-AN ASIAN JOURNAL, 2025, 20 (04)
  • [40] Metal-free synthesis of cyano acrylates via cyanuric chloride-mediated three-component reactions involving a cascade consists of Knoevenagel condensation/cyano hydration/esterification
    Wan, Jie-Ping
    Jing, Yanfeng
    Liu, Yunyun
    Sheng, Shouri
    RSC ADVANCES, 2014, 4 (109) : 63997 - 64000