SO3H-Functionalized Ionic Liquids: Green, Efficient and Reusable Catalysts for the Facile Dehydration of Aldoximes into Nitriles

被引：32

作者：

Davoodnia, Abolghasem ^{[1
]}

Khojastehnezhad, Amir ^{[1
]}

Bakavoli, Mehdi ^{[1
]}

Tavakoli-Hoseini, Niloofar ^{[1
]}

机构：

[1] Islamic Azad Univ, Mashhad Branch, Dept Chem, Fac Sci, Mashhad, Iran

来源：

CHINESE JOURNAL OF CHEMISTRY | 2011年 / 29卷 / 05期

关键词：

ionic liquid; aldoxime; nitrile; dehydration; CONVENIENT ACCESS; ONE-POT; CONVERSION; ALDEHYDES; SYSTEM; KETONES;

D O I：

10.1002/cjoc.201190199

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Easily synthesized aldoximes have been converted to the corresponding nitriles under very mild conditions by a simple reaction using two halogen-free SO3H-functionalized ionic liquids, 3-methyl-1-(4-sulfonic acid)butylimidazolium hydrogen sulfate [MIM(CH2)(4)SO3H][HSO4] and 1-(4-sulfonic acid) butylpyridinium hydrogen sulfate [PY(CH2)(4)SO3H][HSO4], as catalyst and reaction medium without any additional organic solvent. The method was equally effective for aromatic aldoximes bearing electron-donating and electron-withdrawing substituents. Taking into account environmental and economical consideration, the protocol presented here has the merits of environmentally friendly, simple operation, easy work-up and very good yields. The catalysts could be recycled and reused for several times without noticeably decreasing in their catalytic activities.

引用

页码：978 / 982

页数：5

共 37 条

[1]

ATTANASI O, 1983, SYNTHESIS-STUTTGART, P741

[2] Nitration of aromatic compounds with NO2/air catalyzed by sulfonic acid-functionalized ionic liquids [J].

Cheng, Guangbin ;

Duan, Xuelei ;

Qi, Xiufang ;

Lu, Chunxu .

CATALYSIS COMMUNICATIONS, 2008, 10 (02) :201-204

[3] [RuCl2(p-cymene)]2 on carbon:: An efficient, selective, reusable, and environmentally versatile heterogeneous catalyst [J].

Choi, E ;

Lee, C ;

Na, Y ;

Chang, S .

ORGANIC LETTERS, 2002, 4 (14) :2369-2371

[4] Novel bronsted acidic ionic liquids and their use as dual solvent-catalysts [J].

Cole, AC ;

Jensen, JL ;

Ntai, I ;

Tran, KLT ;

Weaver, KJ ;

Forbes, DC ;

Davis, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (21) :5962-5963

[5] A new route to the synthesis of thieno [2,3-d] pyrimidin-4(3H)-one derivatives catalyzed by 12-tungstophosphoric acid (H3PW12O40) [J].

Davoodnia, A. ;

Bakavoli, M. ;

Barakouhi, Gh. ;

Tavakoli-Hoseini, N. .

CHINESE CHEMICAL LETTERS, 2007, 18 (12) :1483-1486

[6] 7-Deazapurines: Synthesis of new pyrrolo[2,3-d]pyrimidin-4-ones catalyzed by a Bronsted-acidic ionic liquid as a green and reusable catalyst [J].

Davoodnia, A. ;

Bakavoli, M. ;

Moloudi, R. ;

Khashi, M. ;

Tavakoli-Hoseini, N. .

CHINESE CHEMICAL LETTERS, 2010, 21 (01) :1-4

[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] Bronsted-acidic ionic liquid [HO3S(CH2)4MIM][HSO4] as efficient and reusable catalyst for one-pot synthesis of β-acetamido ketones [J].

Davoodnia, Abolghasem ;

Heravi, Majid M. ;

Rezaei-Daghigh, Leila ;

Tavakoli-Hoseini, Niloofar .

MONATSHEFTE FUR CHEMIE, 2009, 140 (12) :1499-1502

[9] CYANATION OF AROMATIC HALIDES [J].

ELLIS, GP ;

ROMNEYALEXANDER, TM .

CHEMICAL REVIEWS, 1987, 87 (04) :779-794

[10]

Fatiadi A.J., 1983, Preparation and Synthetic Applications of Cyano Compounds

← 1 2 3 4 →