An eco-benign and highly efficient procedure for N-acylation catalyzed by heteropolyanion-based ionic liquids using carboxylic acid under solvent-free conditions

被引：41

作者：

Chen, Zhikai ^{[1
]}

Fu, Renzhong ^{[2
]}

Chai, Wen ^{[2
]}

Zheng, Hao ^{[1
]}

Sun, Lin ^{[2
]}

Lu, Qiang ^{[2
]}

Yuan, Rongxin ^{[2
]}

机构：

[1] Changzhou Univ, Sch Petrochem Engn, Changzhou 213164, Peoples R China

[2] Changshu Inst Technol, Sch Chem & Mat Engn, Jiangsu Lab Adv Funct Mat, Changshu 215500, Peoples R China

来源：

TETRAHEDRON | 2014年 / 70卷 / 13期

基金：

中国博士后科学基金;

关键词：

Amide; Green chemistry; Ionic liquid; N-acylation; Solvent-free condition; ONE-POT SYNTHESIS; FORMAMIDE DERIVATIVES; ROOM-TEMPERATURE; SECONDARY-AMINES; FORMIC-ACID; FORMYLATION; POLYOXOMETALATE; FACILE; EPOXIDATION; ALKENES;

D O I：

10.1016/j.tet.2014.02.042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An eco-benign and highly efficient route for N-acylation of amines has been developed by treating amines with corresponding carboxylic acids in the presence of 2 mol % of heteropolyanion-based ionic liquids as catalysts under solvent-free conditions. This practical reaction could tolerate a wide range of substrates. Thus, various N-acylation products including N-acyl alpha-amino acid derivatives were obtained in moderate to excellent yields at 70 degrees C to 120 degrees C. Moreover, recycling studies revealed that heteropolyanion-based ionic liquids were easily reusable for this N-acylation. This method provides a green and much improved protocol over the existing methods.(c) 2014 Elsevier Ltd. All rights reserved.

引用

页码：2237 / 2245

页数：9

共 55 条

[1]

Anonymous, 2004, MANAGING INTELLECTUA, P9

[2]

[Anonymous], PARAGRAPH

[3] Silica supported perchloric acid catalyzed rapid N-formylation under solvent-free conditions [J].

Ansari, Mohd Imran ;

Hussain, Mohd Kamil ;

Yadav, Nisha ;

Gupta, Puneet K. ;

Hajela, K. .

TETRAHEDRON LETTERS, 2012, 53 (16) :2063-2065

[4] Protic [TBD][TFA] ionic liquid as a reusable and highly efficient catalyst for N-formylation of amines using formic acid under solvent-free condition [J].

Baghbanian, Seyed Meysam ;

Farhang, Maryam .

JOURNAL OF MOLECULAR LIQUIDS, 2013, 183 :45-49

[5] Amberlite IR-120: A Reusable Catalyst for N-Formylation of Amines with Formic Acid Using Microwaves [J].

Bhojegowd, Madhusudana Reddy Mvthukur ;

Nizam, Aatika ;

Pasha, Mohamed Afzal .

CHINESE JOURNAL OF CATALYSIS, 2010, 31 (05) :518-520

[6] Microwave promoted energy-efficient N-formylation with aqueous formic acid [J].

Bose, Ajay K. ;

Ganguly, Subhendu N. ;

Manhas, Maghar S. ;

Guha, Atri ;

Pombo-Villars, Esteban .

TETRAHEDRON LETTERS, 2006, 47 (27) :4605-4607

[7] A very simple and highly efficient procedure for N-formylation of primary and secondary amines at room temperature under solvent-free conditions [J].

Brahmachari, Goutam ;

Laskar, Sujay .

TETRAHEDRON LETTERS, 2010, 51 (17) :2319-2322

[8] Sulfated tungstate: a new solid heterogeneous catalyst for amide synthesis [J].

Chaudhari, Pramod S. ;

Salim, Suresh D. ;

Sawant, Ravindra V. ;

Akamanchi, Krishnacharya G. .

GREEN CHEMISTRY, 2010, 12 (10) :1707-1710

[9] A new facile method for the synthesis of 1-arylimidazole-5-carboxylates [J].

Chen, BC ;

Bednarz, MS ;

Zhao, RL ;

Sundeen, JE ;

Chen, P ;

Shen, ZQ ;

Skoumbourdis, AP ;

Barrish, JC .

TETRAHEDRON LETTERS, 2000, 41 (29) :5453-5456

[10] Reactivity of ionic liquids [J].

Chowdhury, Shahana ;

Mohan, Ram S. ;

Scott, Janet L. .

TETRAHEDRON, 2007, 63 (11) :2363-2389

← 1 2 3 4 5 6 →