An Effective and New Method for the Synthesis of Polysubstituted Imidazoles by the Use of CrCl3•6H2O as a Green and Reusable Catalyst: Synthasis of Some Novel Imidazole Derivatives

被引：16

作者：

Karami, Bahador ^{[1
,2
]}

Eskandari, Khalil ^{[1
]}

Farahi, Mahnaz ^{[1
]}

Barmas, Akram ^{[2
]}

机构：

[1] Univ Yasuj, Dept Chem, Yasuj 7591874831, Iran

[2] Islamic Azad Univ, Dept Chem, Gachsaran Branch, Gachsaran, Iran

来源：

JOURNAL OF THE CHINESE CHEMICAL SOCIETY | 2012年 / 59卷 / 04期

关键词：

Catalyst; CrCl3 center dot 6H(2)O; Benzil; Polysubstituted imidazoles; ONE-POT SYNTHESIS; TUNGSTATE SULFURIC-ACID; 1,2,4,5-TETRASUBSTITUTED IMIDAZOLES; TETRASUBSTITUTED IMIDAZOLES; MULTICOMPONENT REACTIONS; SUBSTITUTED IMIDAZOLES; EFFICIENT CATALYST; IONIC LIQUID; ALDEHYDES; CHLORIDE;

D O I：

10.1002/jccs.201100555

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

New, efficient and environmentally adapted synthesis of polysubstituted imidazoles in one-pot is found. The multicomponent reaction of various aldehydes, benzil, aliphatic and aromatic primary amines and ammonium acetate under solvent-free condition is explained. The highly efficient role of CrCl3 center dot 6H(2)O as catalyst in this synthesis was shown. By this advantage, several polysubstituted imidazoles as pharmaceutical important molecules can be prepared in high yield and high purity. This method is a very easy and a rapid reaction for the synthesis of imidazole derivatives. The crude products recrystallized to afford the crystalline pure products. Furthermore, catalyst exhibited remarkable reusable activity.

引用

页码：473 / 479

页数：7

共 45 条

[1]

Ahmad S, 2006, J MOL CATAL A-CHEM, V249, P246

[2] A novel one-pot synthesis of tetrasubstituted imidazoles under solvent-free conditions and microwave irradiation [J].

Balalaie, S ;

Hashemi, MM ;

Akhbari, M .

TETRAHEDRON LETTERS, 2003, 44 (08) :1709-1711

[3] One-pot synthesis of tetrasubstituted imidazoles catalyzed by zeolite HY and silica gel under microwave irradiation [J].

Balalaie, S ;

Arabanian, A .

GREEN CHEMISTRY, 2000, 2 (06) :274-276

[4] SULPHUR-METHYLENE ISOSTERISM IN DEVELOPMENT OF METIAMIDE, A NEW HISTAMINE H2-RECEPTOR ANTAGONIST [J].

BLACK, JW ;

DURANT, GJ ;

EMMETT, JC ;

GANELLIN, CR .

NATURE, 1974, 248 (5443) :65-67

[5] An efficient and one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles catalyzed by InCl3•3H2O [J].

Das Sharma, Salkat ;

Hazarika, Parasa ;

Konwar, Dilip .

TETRAHEDRON LETTERS, 2008, 49 (14) :2216-2220

[6] The action of ammonia on benzil [J].

Davidson, D ;

Weiss, M ;

Jelling, M .

JOURNAL OF ORGANIC CHEMISTRY, 1937, 2 (04) :319-327

[7] Green, One-Pot, Solvent-Free Synthesis of 1,2,4,5-Tetrasubstituted Imidazoles Using a BrOnsted Acidic Ionic Liquid as Novel and Reusable Catalyst [J].

Davoodnia, Abolghasem ;

Heravi, Majid M. ;

Safavi-Rad, Zahra ;

Tavakoli-Hoseini, Niloofar .

SYNTHETIC COMMUNICATIONS, 2010, 40 (17) :2588-2597

[8] Potent, orally absorbed glucagon receptor antagonists [J].

de Laszlo, SE ;

Hacker, C ;

Li, B ;

Kim, D ;

MacCoss, M ;

Mantlo, N ;

Pivnichny, JV ;

Colwell, L ;

Koch, GE ;

Cascieri, MA ;

Hagmann, WK .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (05) :641-646

[9] Solubility of imidazoles in ketones [J].

Domanska, U ;

Kozlowska, MK .

FLUID PHASE EQUILIBRIA, 2003, 206 (1-2) :253-266

[10] Catalyst-Free One-Pot Four Component Synthesis of Polysubstituted Imidazoles in Neutral Ionic Liquid 1-Butyl-3-methylimidazolium Bromide [J].

Hasaninejad, Alireza ;

Zare, Abdolkarim ;

Shekouhy, Mohsen ;

Rad, Javad Ameri .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (06) :844-849

← 1 2 3 4 5 →