Highly efficient one-pot synthesis of tetrahydropyridines

被引:15
作者
Ramin, Ghorbani-Vaghei [1 ]
Hajar, Shahbazi [1 ]
机构
[1] Bu Ali Sina Univ, Fac Chem, Dept Organ Chem, Hamadan 65174, Iran
关键词
Multicomponent reaction; One-pot; TBBDA; PBBS; Tetrahydropyridines; Heterocycles; MULTICOMPONENT REACTION; CATALYTIC REAGENTS; N,N,N',N'-TETRABROMOBENZENE-1,3-DISULFONAMIDE; ALDEHYDES; SCAFFOLDS; ALCOHOLS; POLY(N,N'-DIBROMO-N-ETHYL-BENZENE-1,3-DISULFONAMIDE); N,N,N',N'-TETRACHLOROBENZENE-1,3-DISULFONAMIDE; DERIVATIVES; PIPERIDINES;
D O I
10.1016/j.crci.2013.02.015
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The combination of aromatic aldehydes, and 1,3-dicarbonyl compounds in the presence of a catalytic amount of poly(N,N'-dibromo-N-ethyl-benzene-1,3-disulfonamide) [PBBS] and N,N,N',N'-tetrabromobenzene-1,3-disulfonamide [TBBDA] leads to the formation of highly substituted tetrahydropyridines. In this way, a series of pharmacologically interesting substituted piperidine derivatives were obtained in moderate to high yields at room temperature. (C) 2013 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:1047 / 1054
页数:8
相关论文
共 32 条
[1]   Bismuth nitrate-catalyzed multicomponent reaction for efficient and one-pot synthesis of densely functionalized piperidine scaffolds at room temperature [J].
Brahmachari, Goutam ;
Das, Suvankar .
TETRAHEDRON LETTERS, 2012, 53 (12) :1479-1484
[2]   Pot, atom and step economic (PASE) synthesis of highly functionalized piperidines: a five-component condensation [J].
Clarke, Paul A. ;
Zaytzev, Andrey V. ;
Whtwoo, Adrian C. .
TETRAHEDRON LETTERS, 2007, 48 (30) :5209-5212
[3]   One-step synthesis of heterocyclic privileged medicinal scaffolds by a multicomponent reaction of malononitrile with aldehydes and thiols [J].
Evdokimov, Nikolai M. ;
Kireev, Artem S. ;
Yakovenko, Andrey A. ;
Antipin, Mikhail Yu. ;
Magedov, Igor V. ;
Kornienko, Alexander .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (09) :3443-3453
[4]   New three-component reaction:: Novel formation of a seven-membered ring by the unexpected reaction at the γ-position of the β-keto ester [J].
Fujioka, Hiromichi ;
Murai, Kenichi ;
Kubo, Ozora ;
Ohba, Yusuke ;
Kita, Yasuyuki .
ORGANIC LETTERS, 2007, 9 (09) :1687-1690
[5]   Mild and regioselective bromination of aromatic compounds with N,N,N′,N′-tetrabromobenzene-1,3-disulfonylamide an poly (N-bromobenzene-1,3-di-sulfonylamide) [J].
Ghorbani-Vaghei, R ;
Jalili, H .
SYNTHESIS-STUTTGART, 2005, (07) :1099-1102
[6]   Poly(N,N'-dibromo-N-ethyl-benzene-1,3-disulfonamide), N,N,N',N'-tetrabromobenzene-1,3-disulfonamide as new reagents for conjugate addition of indole, pyrrole with α,β-unsaturated ketones [J].
Ghorbani-Vaghei, R. ;
Hajinazari, S. ;
Engashte, M. .
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2012, 9 (05) :655-660
[7]   The application of N,N′-dibromo-N,N′-1,2-ethanediylbis-(p-toluenesulphonamide) as a powerful reagent for the oxidation of primary and secondary alcohols to aldehydes and ketones [J].
Ghorbani-Vaghei, R ;
Khazaei, A .
TETRAHEDRON LETTERS, 2003, 44 (40) :7525-7527
[8]   Poly(N,N′-dibromo-N-ethyl-benzene-1,3-disulfonamide) and N,N,N′,N′-Tetrabromobenzene-1,3-disulfonamide as Effective Catalysts for Conversion of Aldehydes to 1,1-Diacetates and Acetals [J].
Ghorbani-Vaghei, R. ;
Amiri, M. ;
Moshfeghifar, N. ;
Veisi, H. ;
Dadamahaleh, S. Akbari .
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2009, 6 (04) :754-760
[9]   Poly(N,N′-dichloro-N-ethyl-benzene-1,3-disulfonamide, N,N,N′,N′-tetrachlorobenzene-1,3-disulfonamide, Poly(N,N′-dibromo-N-ethyl-benzene-1,3-disulfonamide, and N,N,N′,N′′-Tetrabromobenzene-1,3-disulfonamide Catalyzed Formylation of Amines and Alcohols Using Ethyl Formate under Microwave Irradiation [J].
Ghorbani-Vaghei, R. ;
Veisi, H. ;
Amiri, M. .
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2009, 6 (04) :761-768
[10]  
Ghorbani-Vaghei R., 2009, SYNTHESIS-STUTTGART, V41, P945