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
来源：
TETRAHEDRON LETTERS | 2016年 / 57卷 / 43期
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
  • [41] Transition metal-free synthesis of primary amides from aldehydes and hydroxylamine hydrochloride
    Wang, Wei
    Zhao, Xue-Mei
    Wang, Jing-Li
    Geng, Xin
    Gong, Jun-Fang
    Hao, Xin-Qi
    Song, Mao-Ping
    TETRAHEDRON LETTERS, 2014, 55 (20) : 3192 - 3194
  • [42] Metal free, I2-catalyzed [3+1+1] cycloaddition reactions to synthesize 1,2,4-trisubstituted imidazoles
    Tang, Dong
    Guo, Xin
    Wang, Yu
    Wang, Jing
    Li, Jihui
    Huang, Qiangwei
    Chen, Baohua
    TETRAHEDRON LETTERS, 2015, 56 (44) : 5982 - 5985
  • [43] Synthesis of fused pyrroles containing 4-hydroxycoumarins by regioselective metal-free multicomponent reactions
    Mishra, Richa
    Jana, Asim
    Panday, Anoop Kumar
    Choudhury, Lokman H.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (17) : 3289 - 3302
  • [44] The synthesis and structure of 1,3,4-trisubstituted 2,5-dioxopyrrolidines and their behaviour in liquid crystalline systems
    Galatina, AI
    Derkach, LG
    Kilimenchuk, HD
    Kondratyeva, RV
    Novikova, NS
    Jarovoy, JK
    LIQUID CRYSTALS, 2000, 27 (09) : 1229 - 1233
  • [45] N-Alkylhydrazones of aliphatic ketones in the synthesis of 1,3,4-trisubstituted non-symmetric pyrazoles
    Ivonin, Sergey P.
    Kurpil, Bohdan B.
    Rusanov, Eduard B.
    Grygorenko, Oleksandr O.
    Volochnyuk, Dmitry M.
    TETRAHEDRON LETTERS, 2014, 55 (14) : 2187 - 2189
  • [46] Metal-free synthesis of 1,3,5-trisubstituted benzenes by the cyclotrimerization of enaminones or alkynes in water
    Wan, Jie-Ping
    Lin, Yunfang
    Hu, Kaikai
    Liu, Yunyun
    RSC ADVANCES, 2014, 4 (39) : 20499 - 20505
  • [47] Synthesis of 1,3,4-trisubstituted pyrrolidines as meropenem adjuvants targeting New Delhi metallo-β-lactamase
    Jin, Wen Bin
    Xu, Chen
    Qi, Xiao Lin
    Zeng, Ping
    Gao, Wei
    Lai, Ki Hon
    Chiou, Jiachi
    Chan, Edward W. C.
    Leung, Yun-Chung
    Chan, Tak Hang
    Wong, Kwok-Yin
    Chen, Sheng
    Chan, Kin-Fai
    NEW JOURNAL OF CHEMISTRY, 2021, 45 (07) : 3515 - 3534
  • [48] A Simple and Efficient Metal-Free Synthesis of Tetrasubstituted Pyrroles by Iodine-Catalyzed Four-Component Coupling Reaction of Aldehydes, Amines, Dialkyl Acetylenedicarboxylates, and Nitromethane
    Das, Biswanath
    Bhunia, Nisith
    Lingaiah, Maram
    SYNTHESIS-STUTTGART, 2011, (21): : 3471 - 3474
  • [49] STEREOSPECIFIC SYNTHESIS OF TRANS, CIS-1,3,4-TRISUBSTITUTED 1,2,3,4-TETRAHYDRO-BETA-CARBOLINES
    BEHFOROUZ, M
    WEST, SJ
    CHAKRABARTY, C
    RUSK, DA
    ZARRINMAYEH, H
    HETEROCYCLES, 1992, 34 (03) : 483 - 495
  • [50] ENANTIOSELECTIVE SYNTHESIS AND ANTIELASTASE ACTIVITY OF 1,3,4-TRISUBSTITUTED AND 3,4-DISUBSTITUTED BETA-LACTAM ANTIBIOTICS
    ADONIAS, M
    ANAYA, J
    CAMARA, J
    CANET, E
    GATEAUOLESKER, A
    GERO, SD
    GRANDE, M
    HERNANDO, JIM
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (12) : 2547 - 2552
12345