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
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
  • [1] Four-component reaction between cyclohexyl isocyanide, aromatic aldehydes, aromatic amines and trifluoroacetic anhydride
    Anary-Abbasinejad, Mohammad
    Anaraki-Ardakani, Hossein
    Rasekh, Maryam
    Tabatabaee, Masoumeh
    Nazari, Ali
    JOURNAL OF CHEMICAL RESEARCH, 2010, (05) : 259 - 262
  • [2] Synthesis of Polysubstituted Dihydropyridines by Four-Component Reactions of Aromatic Aldehydes, Malononitrile, Arylamines, and Acetylenedicarboxylate
    Sun, Jing
    Xia, Er-Yan
    Wu, Qun
    Yan, Chao-Guo
    ORGANIC LETTERS, 2010, 12 (16) : 3678 - 3681
  • [3] Three-component Reaction of 2-Aminobenzothiazole with Methylene-active Carbonyl Compounds and Aldehydes
    A. A. Pavlenko
    Kh. S. Shikhaliev
    A. Yu. Potapov
    D. V. Krylsky
    Chemistry of Heterocyclic Compounds, 2005, 41 (5) : 689 - 690
  • [4] The double four-component Ugi reaction between squaramic or squaramide acids with alkyl isocyanides, amines and aromatic aldehydes
    Mehrabi, Hossein
    Saleki, Tahereh
    JOURNAL OF CHEMICAL RESEARCH, 2015, (04) : 195 - 198
  • [5] FOUR-COMPONENT SYNTHESIS OF FUNCTIONALIZED 1, 3, 4-OXADIAZOLE DERIVATIVES BEARING THE 2-AMINOBENZOTHIAZOLE MOIETY
    Rastkar, Milad Bazaz
    Mohtat, Bita
    Marandi, Gholam Bagheri
    Djahaniani, Hoorieh
    HETEROCYCLES, 2021, 102 (10) : 1969 - 1981
  • [6] Four-component reaction between aryl aldehydes, ethyl cyanoacetate and dimethyl acetylenedicarboxylate in the presence of cyclohexyl isocyanide
    Anary-Abbasinejad, Mohammad
    Hassanabadi, Alireza
    Aiinparast, Farzaneh
    JOURNAL OF CHEMICAL RESEARCH, 2010, (11) : 613 - 615
  • [7] Synthesis of Functionalized Thiophenes by Four-component Reactions of 1,3-Thiazolidinedione, Aromatic Aldehydes, Cyanoacetamide and Cyclic Secondary Amines
    Yao Rong
    Xia Eryan
    Sun Jing
    Yan Chaoguo
    CHINESE JOURNAL OF CHEMISTRY, 2011, 29 (11) : 2461 - 2464
  • [8] On reaction of epichlorohydrine with 2-aminobenzothiazole and its derivatives
    Ambartsumova, RF
    Kosmacheva, LP
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2001, (07): : 993 - 997
  • [9] ON THE REACTION OF 2-CHLORONICOTINIC ACID WITH 2-AMINOBENZOTHIAZOLE
    GARIN, J
    MELENDEZ, E
    MERCHAN, FL
    TEJERO, T
    HETEROCYCLES, 1986, 24 (01) : 87 - 91
  • [10] Reaction of epichlorohydrin with 2-aminobenzothiazole and its derivatives
    Ambartsumova R.F.
    Kosmacheva L.P.
    Chemistry of Heterocyclic Compounds, 2001, 37 (07) : 916 - 917