Catalyst-free synthesis of functionalized dihydro-2-oxypyrroles by the reaction of enaminones and N,N′-bis(phenylmethylidene) phenylmethane

被引:5
|
作者
Alizadeh, Abdolali [1 ]
Mokhtari, Javad [1 ]
Zhu, Long-Guan [2 ]
机构
[1] Tarbiat Modares Univ, Dept Chem, Tehran, Iran
[2] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China
关键词
Primary amine; Dialkyl acetylenedicarboxylate; N; '-bis(phenylmethylidene)phenylmethane; Dihydro-2-oxypyrrole; Three-component reaction; AROMATIC-ALDEHYDES; ALKALOIDS;
D O I
10.1016/j.crci.2013.01.020
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A catalyst-free and convenient approach for the preparation of substituted dihydro-2-oxypyrrole is described. This three-component reaction between primary amines, dialkyl acetylenedicarboxylate, and N,N'-bis(phenylmethylidene)phenylmethane proceeds in MeOH under reflux conditions in good to excellent yields. (C) 2013 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:863 / 867
页数:5
相关论文
共 50 条
  • [31] A novel catalyst-free method for the synthesis of mono-N-substituted thioureas in water
    Kaboudin, Babak
    Hajmohammadi, Elham
    Sohrabi, Masoumeh
    Kazemi, Foad
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2024, 21 (02) : 561 - 567
  • [32] A novel catalyst-free method for the synthesis of mono-N-substituted thioureas in water
    Babak Kaboudin
    Elham Hajmohammadi
    Masoumeh Sohrabi
    Foad Kazemi
    Journal of the Iranian Chemical Society, 2024, 21 : 561 - 567
  • [33] Imin-based synthesis of polyfunctionalized dihydro-2-oxypyrroles catalyzed by glycine amino acid via tandem Michael-Mannich cyclocondensation reaction under ambient temperature
    Mohamadpour, Farzaneh
    RESEARCH ON CHEMICAL INTERMEDIATES, 2020, 46 (03) : 1931 - 1940
  • [34] A catalyst-free N-H insertion/Mannich-type reaction cascade of α-nitrodiazoesters
    Yang, Ting
    Zhuang, Hao
    Lin, Xichen
    Xiang, Jia-Ning
    Elliott, John D.
    Liu, Lianghui
    Ren, Feng
    TETRAHEDRON LETTERS, 2013, 54 (32) : 4159 - 4163
  • [35] On water: catalyst-free chemoselective synthesis of highly functionalized tetrahydroquinazolines from 2-aminophenylacrylate
    Saunthwal, Rakesh K.
    Patel, Monika
    Tiwari, Rakesh K.
    Parang, Keykavous
    Verma, Akhilesh K.
    GREEN CHEMISTRY, 2015, 17 (03) : 1434 - 1441
  • [36] A novel catalyst-free mechanochemical protocol for the synthesis of 2,3-dihydro-1H-perimidines
    Harry, Nissy Ann
    Radhika, Sankaran
    Neetha, Mohan
    Anilkumar, Gopinathan
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (04) : 2037 - 2043
  • [37] Catalyst-free three-component synthesis of highly functionalized 2,3-dihydropyrroles
    Wang, Dong
    Li, Linna
    Feng, Hairong
    Sun, Hua
    Almeida-Veloso, Fabrice
    Charavin, Marine
    Yu, Peng
    Desaubry, Laurent
    GREEN CHEMISTRY, 2018, 20 (12) : 2775 - 2780
  • [38] A catalyst-free and expeditious general synthesis of N-benzyl-N-arylcyanamides under ultrasound irradiation at room temperature
    Nasrollahzadeh, Mahmoud
    Sajjadi, Mohaddeseh
    Varma, Rajender S.
    ULTRASONICS SONOCHEMISTRY, 2019, 56 : 481 - 486
  • [39] Synthesis of 2-Aryl-5-oxo-4-[2-(phenylmethylidene)hydrazino]-2,5-dihydro-1H-pyrrole-3-carboxylates by the Reaction between Hydrazones, Acetylenedicarboxylates, and 1-Aryl-N,N′-bis(arylmethylidene)methanediamines
    Alizadeh, Abdolali
    Saberi, Vahid
    Mokhtari, Javad
    HELVETICA CHIMICA ACTA, 2013, 96 (10) : 1991 - 1996
  • [40] A Novel Catalyst-Free Tandem Reaction for the Synthesis of 5-Hydroxy-1,5-dihydro-2H-pyrrol-2-ones in Water Medium
    Wu, Ming-Yu
    Li, Kun
    Wang, Na
    He, Ting
    Yu, Xiao-Qi
    SYNTHESIS-STUTTGART, 2011, (12): : 1831 - 1839