A Novel Ionic Liquid Based on Imidazolium Cation as an Efficient and Reusable Catalyst for the One-pot Synthesis of Benzoxazoles, Benzthiazoles, Benzimidazoles and 2-Arylsubstituted Benzimidazoles

被引：8

作者：

Hasanpour, Maede ^{[1
]}

Eshghi, Hossein ^{[1
]}

Bakavoli, Mehdi ^{[1
]}

Mirzaei, Mahdi ^{[1
]}

机构：

[1] Ferdowsi Univ Mashhad, Sch Sci, Dept Chem, Mashhad 917751436, Iran

来源：

JOURNAL OF THE CHINESE CHEMICAL SOCIETY | 2015年 / 62卷 / 05期

关键词：

Ionic liquid; Imidazolium cation; Benzoxazoles; Benzthiazoles; Benzimidazoles; Reusable catalyst; HETEROGENEOUS CATALYST; DERIVATIVES; BENZOTHIAZOLES; MILD; OXIDATION; 2-ARYLBENZIMIDAZOLE; PHENYLENEDIAMINE; HETEROCYCLES; COMPLEX; DESIGN;

D O I：

10.1002/jccs.201400372

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel dicationic ionic liquid based on imidazolium cation is designed, synthesized and successfully used as catalyst for the one-pot synthesis of benzoxazoles, benzthiazoles, benzimidazoles and 2-arylsubstituted benzimidazoles. The remarkable feature of this new catalyst is its ethyleneoxy bridge which participates in dissolving organic compound in ionic liquid. The application of this ionic liquid is studied in a new one-pot method for synthesis of heterocyclic compounds under solvent-free conditions. Simple and convenient procedure, high conversion, reusability of catalyst, easy purification and shorter reaction time are the advantageous features of this method.

引用

页码：412 / 419

页数：8

共 52 条

[31] Design and synthesis of novel imidazolium-based ionic liquids with a pseudo crown-ether moiety: diastereomeric interaction of a racemic ionic liquid with enantiopure europium complexes [J].

Ishida, Y ;

Sasaki, D ;

Miyauchi, H ;

Saigo, K .

TETRAHEDRON LETTERS, 2004, 45 (51) :9455-9459

[32]

Itoh T, 2004, HETEROCYCLES, V63, P2769

[33] Efficient selective dehydration of fructose and sucrose into 5-hydroxymethylfurfural (HMF) using dicationic room temperature ionic liquids as a catalyst [J].

Jadhav, Arvind H. ;

Kim, Hern ;

Hwang, In Taek .

CATALYSIS COMMUNICATIONS, 2012, 21 :96-103

[34] Synthesis and evaluation of anticancer benzoxazoles and benzimidazoles related to UK-1 [J].

Kumar, D ;

Jacob, MR ;

Reynolds, MB ;

Kerwin, SM .

BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (12) :3997-4004

[35] [bmim]Br3as a new reagent for regioselective monobromination of arylamines under solvent-free conditions [J].

Le, ZG ;

Chen, ZC ;

Hu, Y ;

Zheng, QG .

SYNTHESIS-STUTTGART, 2004, (17) :2809-2812

[36] A study of the ionic liquid mediated microwave heating of organic solvents [J].

Leadbeater, NE ;

Torenius, HM .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (09) :3145-3148

[37] Traceless solid-phase synthesis of 5-benzoylbenzimidazoles [J].

Lee, KJ ;

Janda, KD .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2001, 79 (11) :1556-1561

[38] Study on the relationship between the interaction energy and the melting point of amino acid cation based ionic liquids [J].

Li, Wei ;

Wu, Xinmin ;

Qi, Chuansong ;

Rong, Hua ;

Gong, Liangfa .

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2010, 942 (1-3) :19-25

[39] Mild and efficient synthesis of benzoxazoles, benzothiazoles, benzimidazoles, and oxazolo[4,5-b]pyridines catalyzed by Bi(III) salts under solvent-free conditions [J].

Mohammadpoor-Baltork, Iraj ;

Khosropour, Ahmad R. ;

Hojati, Seyedeh F. .

MONATSHEFTE FUR CHEMIE, 2007, 138 (07) :663-667

[40] PURINES .51. SYNTHESIS AND BIOLOGICAL-ACTIVITY OF HYPOXANTHINE 7-N-OXIDE AND RELATED-COMPOUNDS [J].

OGAWA, K ;

NISHII, M ;

NOHARA, F ;

SAITO, T ;

ITAYA, T ;

FUJII, T .

CHEMICAL & PHARMACEUTICAL BULLETIN, 1992, 40 (03) :612-616

← 1 2 3 4 5 6 →