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
  • [1] CATALYST-FREE SYNTHESIS OF α-AMINOACYL-AMIDES VIA N,N′-BIS(PHENYLMETHYLIDENE)PHENYLMETHANEDIAMINE AS IMINE SURROGATE IN UGI MULTICOMPONENT REACTION
    Alizadeh, Abdolali
    Mokhtari, Javad
    SYNTHETIC COMMUNICATIONS, 2012, 42 (05) : 686 - 693
  • [2] Formic acid as a natural green and bio-based catalyst promoted for the facile synthesis of functionalized dihydro-2-oxypyrroles under ambient temperature
    Mohamadpour, Farzaneh
    UPB Scientific Bulletin, Series B: Chemistry and Materials Science, 2019, 81 (01): : 96 - 102
  • [3] FORMIC ACID AS A NATURAL GREEN AND BIO-BASED CATALYST PROMOTED FOR THE FACILE SYNTHESIS OF FUNCTIONALIZED DIHYDRO-2-OXYPYRROLES UNDER AMBIENT TEMPERATURE
    Mohamadpour, Farzaneh
    UNIVERSITY POLITEHNICA OF BUCHAREST SCIENTIFIC BULLETIN SERIES B-CHEMISTRY AND MATERIALS SCIENCE, 2019, 81 (01): : 95 - 102
  • [4] Synthesis of functionalized dihydro-2-oxypyrroles and tetrahydropyridines using 2,6-pyridinedicarboxylic acid as an efficient and mild organocatalyst
    Khan, Md Musawwer
    Khan, Sarfaraz
    Iqbal, Safia
    Saigal
    Yousuf, Raveed
    NEW JOURNAL OF CHEMISTRY, 2016, 40 (09) : 7504 - 7512
  • [5] Al(H2PO4)3 as an efficient and reusable catalyst for the multi-component synthesis of highly functionalized piperidines and dihydro-2-oxypyrroles
    Seyed Sajad Sajadikhah
    Nourallah Hazeri
    Malek Taher Maghsoodlou
    Sayyed Mostafa Habibi-Khorassani
    Adel Beigbabaei
    Anthony C. Willis
    Journal of the Iranian Chemical Society, 2013, 10 : 863 - 871
  • [6] Al(H2PO4)3 as an efficient and reusable catalyst for the multi-component synthesis of highly functionalized piperidines and dihydro-2-oxypyrroles
    Sajadikhah, Seyed Sajad
    Hazeri, Nourallah
    Maghsoodlou, Malek Taher
    Habibi-Khorassani, Sayyed Mostafa
    Beigbabaei, Adel
    Willis, Anthony C.
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2013, 10 (05) : 863 - 871
  • [7] CAFFEINE AS A NATURALLY GREEN AND BIODEGRADABLE CATALYST PROMOTED CONVENIENT AND EXPEDIENT SYNTHETIC ROUTE FOR THE SYNTHESIS OF POLYSUBSTITUTED DIHYDRO-2-OXYPYRROLES
    Mohamadpour, Farzaneh
    BULLETIN OF THE CHEMICAL SOCIETY OF ETHIOPIA, 2019, 33 (01) : 149 - 158
  • [8] Synthesis of enaminones containing diverse N,N-disubstitution via simple transamination: a study with sustainable catalyst-free operation
    Yong Gao
    Yunyun Liu
    Li Wei
    Jieping Wan
    Research on Chemical Intermediates, 2017, 43 : 5547 - 5555
  • [9] Synthesis of enaminones containing diverse N,N-disubstitution via simple transamination: a study with sustainable catalyst-free operation
    Gao, Yong
    Liu, Yunyun
    Wei, Li
    Wan, Jieping
    RESEARCH ON CHEMICAL INTERMEDIATES, 2017, 43 (10) : 5547 - 5555
  • [10] Catalyst-Free and Stereoselective Synthesis of N,N-Bicyclic Pyrazolidinone Derivatives
    Yang, Desuo
    Fan, Mingjin
    Zhu, Haiyun
    Guo, Yaning
    Guo, Jiangtao
    SYNTHESIS-STUTTGART, 2013, 45 (10): : 1325 - 1332