An efficient FeCl3/SiO2 NPs as a reusable heterogeneous catalyzed five-component reactions of tetrahydropyridines under mild conditions

被引:24
作者
Safaei-Ghomi, Javad [1 ]
Ziarati, Abolfazl [1 ]
机构
[1] Univ Kashan, Fac Chem, Dept Organ Chem, Kashan 51167, Iran
关键词
Tetrahydropyridines; Five-component; Nano silica; Reusable catalyst; One pot; ONE-POT SYNTHESIS; DIELS-ALDER REACTION; MULTICOMPONENT REACTIONS; ASYMMETRIC-SYNTHESIS; CONCISE SYNTHESIS; DERIVATIVES; PIPERIDINES; ATOM;
D O I
10.1007/s13738-012-0134-z
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A convenient, simple, and multicomponent coupling strategy has been developed for the synthesis of highly functionalized tetrahydropyridines using FeCl3/SiO2 NPs as catalyst. This method demonstrated five-component coupling reactions of 1,3-dicarbonyl compounds, aromatic aldehydes and amines without an inert atmosphere. Atom economy, good yields, environmentally benign, and mild reaction conditions are some of the important features of this protocol. Notably, this catalyst could be recycled and reused for several times without noticeably decreasing the catalytic activity.
引用
收藏
页码:135 / 139
页数:5
相关论文
共 23 条
[1]   A novel highly selective chiral auxiliary for the asymmetric synthesis of L- and D-α-amino acid derivatives via a multicomponent Ugi reaction [J].
Basso, A ;
Banfi, L ;
Riva, R ;
Guanti, G .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (02) :575-579
[2]   Heterocycles derived from heteroatom-substituted carbenes [J].
Cheng, Y ;
Meth-Cohn, O .
CHEMICAL REVIEWS, 2004, 104 (05) :2507-2530
[3]   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
[4]   Intramolecular Mannich reaction in the asymmetric synthesis of polysubstituted piperidines: Concise synthesis of the dendrobate alkaloid (+)-241D and its C-4 epimer [J].
Davis, FA ;
Chao, B ;
Rao, A .
ORGANIC LETTERS, 2001, 3 (20) :3169-3171
[5]   Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].
Dömling, A .
CHEMICAL REVIEWS, 2006, 106 (01) :17-89
[6]  
Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
[7]  
2-U
[8]   Catalytic asymmetric inverse-electron-demand Diels-Alder reaction of N-sulfonyl-1-aza-1,3-dienes [J].
Esquivias, Jorge ;
Gomez Arrayas, Ramon ;
Carretero, Juan C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (06) :1480-+
[9]   Enantioselective organocatalytic intramolecular aza-Michael reaction:: a concise synthesis of (+)-sedamine., (+)-allosedamine, and (+)-coniine [J].
Fustero, Santos ;
Jimenez, Diego ;
Moscardo, Javier ;
Catalan, Silvia ;
del Pozo, Carlos .
ORGANIC LETTERS, 2007, 9 (25) :5283-5286
[10]   Synthesis and structure-activity relationships of potential anticonvulsants based on 2-piperidinecarboxylic acid and related pharmacophores [J].
Ho, B ;
Crider, AM ;
Stables, JP .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2001, 36 (03) :265-286