Efficient and extremely facile one-pot four-component synthesis of mono and bis-N-aryl/alkyl-3-aminodihydropyrrol-2-one-4-carboxylates catalyzed by p-TsOH•H2O

被引：9
|
作者：
Sajadikhah, Seyed Sajad [1 ]
Maghsoodlou, Malek Taher [2 ]
Hazeri, Nourallah [2 ]
机构：
[1] Islamic Azad Univ, Najafabad Branch, Dept Chem, Fac Sci, Najafabad, Esfahan, Iran
[2] Univ Sistan & Baluchestan, Dept Chem, Fac Sci, Zahedan, Iran
来源：
RESEARCH ON CHEMICAL INTERMEDIATES | 2015年 / 41卷 / 04期
关键词：
Dihydropyrrol-2-one; Heterocycle; p-TsOH center dot H2O; Four-component reaction; MULTICOMPONENT SYNTHESIS; DOMINO REACTION; INHIBITORS; ACETYLENEDICARBOXYLATES; 1,5-DIHYDROPYRROL-2-ONES; DIHYDROPYRROLES; DERIVATIVES; ARYLAMINES; ACIDS;
D O I：
10.1007/s11164-013-1364-0
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient and straightforward procedure has been developed for synthesis of mono and bis-N-aryl/alkyl-3-aminodihydropyrrol-2-one-4-carboxylates via one-pot four-component domino reaction of amines, dialkyl acetylenedicarboxylates, and formaldehyde, in the presence of p-TsOH center dot H2O (15 mol%), in MeOH at ambient temperature. The salient advantages of this method are mild reaction conditions, high to excellent yields, shorter reaction times, atom economy, easy operation, and no column chromatographic separation.
引用
收藏
页码：2503 / 2511
页数：9
相关论文
共 50 条
  • [1] Efficient and extremely facile one-pot four-component synthesis of mono and bis-N-aryl/alkyl-3-aminodihydropyrrol-2-one-4-carboxylates catalyzed by p-TsOH·H2O
    Seyed Sajad Sajadikhah
    Malek Taher Maghsoodlou
    Nourallah Hazeri
    Research on Chemical Intermediates, 2015, 41 : 2503 - 2511
  • [2] A simple and efficient approach to one-pot synthesis of mono- and bis-N-aryl-3-aminodihydropyrrol-2-one-4-carboxylates catalyzed by InCl3
    Sajadikhah, Seyed Sajad
    Maghsoodlou, Malek Taher
    Hazeri, Nourallah
    CHINESE CHEMICAL LETTERS, 2014, 25 (01) : 58 - 60
  • [3] A one-pot multi-component synthesis of N-aryl-3-aminodihydropyrrol-2-one-4-carboxylates catalysed by oxalic acid dihydrate
    Sajadikhah, Seyed Sajad
    Hazeri, Nourallah
    Maghsoodlou, Malek Taher
    Habibi-Khorassani, Sayyed Mostafa
    Khandan-Barani, Khatereh
    JOURNAL OF CHEMICAL RESEARCH, 2013, (01) : 40 - 42
  • [4] Ascorbic acid: a naturally green and efficient catalyst for one-pot synthesis of N-aryl-3-aminodihydropyrrol-2-one-4-carboxylates under ambient temperature
    Mohamadpour, Farzaneh
    BIOINTERFACE RESEARCH IN APPLIED CHEMISTRY, 2019, 9 (06): : 4458 - 4462
  • [5] Vitamin B12: An efficient type catalyst for the one-pot synthesis of 3,4,5-trisubstituted furan-2(5H)-ones and N-aryl-3-aminodihydropyrrol-2-one-4-carboxylates
    Kangani, Mehrnoosh
    Maghsoodlou, Malek-Taher
    Hazeri, Nourallah
    CHINESE CHEMICAL LETTERS, 2016, 27 (01) : 66 - 70
  • [6] Facile one-pot synthesis of novel dicyanoanilines fused to tetrahydro-4H-thiopyran-4-one ring via Et3N/H2O catalyzed pseudo four-component reaction
    Abaee, M. Saeed
    Forghani, Soodabeh
    Mojtahedi, Mohammad M.
    Harms, Klaus
    JOURNAL OF SULFUR CHEMISTRY, 2016, 37 (06) : 683 - 691
  • [7] ZrCl4 as an efficient catalyst for one-pot four-component synthesis of polysubstituted dihydropyrrol-2-ones
    Sajadikhah, Seyed Sajad
    Maghsoodlou, Malek Taher
    Hazeri, Nourallah
    Mohamadian-Souri, Sajad
    RESEARCH ON CHEMICAL INTERMEDIATES, 2016, 42 (04) : 2805 - 2814
  • [8] A Xylose-Catalyzed One-Pot Four-Component Domino Protocol for the Facile Synthesis of Highly Substituted Dihydropyrrol-2-ones
    Sajadikhah, Seyed Sajad
    Maghsoodlou, Malek Taher
    Hazeri, Nourallah
    Moein, Maryam
    Norouzi, Mahmoud
    Mohamadian-Souri, Sajad
    LETTERS IN ORGANIC CHEMISTRY, 2014, 11 (04) : 268 - 272
  • [9] An efficient synthesis of 3-aryl-2,3-dihydrothiophene-2-carboxamide derivatives by one-pot, four-component reaction
    Teng, Da
    Xia, Sheng
    Tao, Shimin
    Gao, Lijiu
    Feng, Youjian
    Rong, Liangce
    RESEARCH ON CHEMICAL INTERMEDIATES, 2013, 39 (02) : 561 - 568
  • [10] Potassium alum as a naturally mineral and economical catalyst for the one-pot, multi-component and clean synthesis of 2-oxo(thio)-1,2,3,4-teirahydropyrimidines and N-aryl-3-aminodihydropyrrol-2-one-4-carboxylates
    Mohamadpour, Farzaneh
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2020, 59 (08): : 1183 - 1190
12345