Four-component reaction of cyclic amines, 2-aminobenzothiazole, aromatic aldehydes and acetylenedicarboxylate

被引：10
|
作者：
Gao, Hong [1 ]
Sun, Jing [1 ]
Yan, Chao-Guo [1 ]
机构：
[1] Yangzhou Univ, Coll Chem & Chem Engn, Yangzhou 225002, Peoples R China
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 9卷
基金：
中国国家自然科学基金;
关键词：
benzothiazole; domino reaction; electron-deficient alkyne; multicomponent reaction; pyrrolidinone; QUINOLINE-DMAD ZWITTERION; MULTICOMPONENT SYNTHESIS; FACILE SYNTHESIS; DIALKYL ACETYLENEDICARBOXYLATES; 1,4-DIPOLAR CYCLOADDITION; 3-COMPONENT REACTION; EFFICIENT SYNTHESIS; METHYL PROPIOLATE; DOMINO REACTIONS; ARYLAMINES;
D O I：
10.3762/bjoc.9.330
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The four-component reaction of 2-aminobenzothiazole, aromatic aldehydes, acetylenedicarboxylate and piperidine or pyrrolidine in ethanol afforded the functionalized 2-pyrrolidinones containing both benzothiazolyl and piperidinyl (or pyrrolidinyl) units in good yields. On the other hand, the similar four-component reactions resulted in the functionalized morpholinium or piperidinium 2-pyrrolidinon-3-olates in the presence of p-toluenesulfonic acid.
引用
收藏
页码：2934 / 2939
页数：6
相关论文
共 50 条
  • [41] THE REACTION OF ALDEHYDES AND AROMATIC AMINES WITH 8-QUINOLINOL
    PHILLIPS, JP
    KEOWN, R
    FERNANDO, Q
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (17) : 4306 - 4307
  • [42] THE MANNICH REACTION OF BUTANONE, AROMATIC-ALDEHYDES AND AROMATIC-AMINES
    YI, L
    ZOU, JH
    LEI, HS
    HE, QL
    SYNTHETIC COMMUNICATIONS, 1991, 21 (20) : 2109 - 2117
  • [43] The Mannich reaction of 4-methylacetophenone with aromatic aldehydes and aromatic amines
    Yang, DC
    Zhang, GL
    Yang, Y
    Zhong, YG
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2000, 21 (11): : 1694 - 1696
  • [44] Coordination compounds in a pentacyclic aromatic system from 2-aminobenzothiazole derivatives and transition metal ions
    Tellez, Fabiola
    Pena-Hueso, Adrian
    Barba-Behrens, Norah
    Contreras, Rosalinda
    Flores-Parra, Angelina
    POLYHEDRON, 2006, 25 (12) : 2363 - 2374
  • [45] 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
  • [46] A novel synthesis of aminofurans using a four-component reaction
    Alizadeh, Abdolali
    Rostamnia, Sadegh
    Zoreh, Nasrin
    Oskueyan, Qasem
    SYNLETT, 2007, (10) : 1610 - 1612
  • [47] Four-component tandem reaction to synthesize dihydrotetrazolopyrimidinyl carbamides
    Zeng, Li-Yan
    Ji, Fei
    Cai, Chun
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (01) : 237 - 241
  • [48] Synthesis of stable ketenimines via a four-component reaction
    Abdolali Alizadeh
    Mahdi Ahmadi
    Monatshefte für Chemie - Chemical Monthly, 2011, 142 : 1249 - 1252
  • [49] Four-component domino reaction leading to multifunctionalized quinazolines
    Jiang, Bo
    Tu, Shu-Jiang
    Kaur, Parminder
    Wever, Walter
    Li, Guigen
    Journal of the American Chemical Society, 2009, 131 (33): : 11660 - 11661
  • [50] An efficient, four-component reaction for the synthesis of novel carbamodithioates
    Sadat-Ebrahimi, Seyed Esmail
    Karim, Leila
    Moghimi, Setareh
    Yahya-Meymandi, Azadeh
    Mahdavi, Mohammad
    Vosooghi, Mohsen
    Foroumadi, Alireza
    Shafiee, Abbas
    JOURNAL OF SULFUR CHEMISTRY, 2017, 38 (01) : 43 - 51
12345