Ionic liquid-promoted dehydration of aldoximes: a convenient access to aromatic, heteroaromatic and aliphatic nitriles

被引：36

作者：

Saha, Debasree ^{[1
]}

Saha, Amit ^{[1
]}

Ranu, Brindaban C. ^{[1
]}

机构：

[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, India

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 44期

关键词：

Aldoxime; Nitrile; Dehydration; Ionic liquid; Organic solvent-free reaction; CATALYTIC BECKMANN REARRANGEMENT; OXIDATIVE CONVERSION; MICHAEL ADDITION; SOLVENT; OXIMES; REAGENT; CYANATION; EPOXIDES; SYSTEM; AMIDES;

D O I：

10.1016/j.tetlet.2009.08.069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and convenient procedure for the synthesis of nitrites by dehydration of aldoximes using an ionic liquid, 1-pentyl-3-methylimidazolium tetrafluoroborate, [pmim]BF4 under organic solvent-free condition, has been developed. A variety of aromatic, heteroaromatic and aliphatic aldoximes are converted to the corresponding nitrites. The ionic liquid is recovered and reused for subsequent reactions. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：6088 / 6091

页数：4

共 44 条

[1] Direct oxidative conversion of aldehydes to nitriles using IBX in aqueous ammonia [J].

Arote, Nitin D. ;

Bhalerao, Dinesh S. ;

Akamanchi, Krishnacharya G. .

TETRAHEDRON LETTERS, 2007, 48 (21) :3651-3653

[2] P(CH3NCH2CH2)(3)N: A nonionic superbase for efficient dehydrohalogenation [J].

Arumugam, S ;

Verkade, JG .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) :4827-4828

[3] AlCl3•6H2O/KI/H2O/CH3CN:: A new alternate system for dehydration of oximes and amides in hydrated media [J].

Boruah, M ;

Konwar, D .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :7138-7139

[4] Laboratory-scale synthesis of Nitriles by catalysed dehydration of Amides and Oximes under flash vacuum pyrolysis (FVP) conditions [J].

Campbell, Jacqueline A. ;

McDougald, Graham ;

Mcnab, Hamish ;

Rees, Lovat V. C. ;

Tyas, Richard G. .

SYNTHESIS-STUTTGART, 2007, (20) :3179-3184

[5] On Catalysis by Ionic Liquids [J].

Chakraborti, Asit K. ;

Roy, Sudipta Raha .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (20) :6902-+

[6] Thionyl chloride-benzotriazole: An efficient system for transformation of aldoximes to nitriles [J].

Chaudhari, SS ;

Akamanchi, KG .

SYNTHETIC COMMUNICATIONS, 1999, 29 (10) :1741-1745

[7] Oxidative conversion of amines into their corresponding nitriles using o-iodoxybenzoic acid (IBX)/iodine:: Selective oxidation of aminoalcohols to hydroxynitriles [J].

Chiampanichayakul, Supanimit ;

Pohmakotr, Manat ;

Reutrakul, Vichai ;

Jaipetch, Thaworn ;

Kuhakarn, Chutima .

SYNTHESIS-STUTTGART, 2008, (13) :2045-2048

[8] Ionic liquid catalyst for biphasic atom transfer radical polymerization of methyl methacrylate [J].

Ding, SJ ;

Radosz, M ;

Shen, YQ .

MACROMOLECULES, 2005, 38 (14) :5921-5928

[9] Paradigm confirmed: The first use of ionic liquids to dramatically influence the outcome of chemical reactions [J].

Earle, MJ ;

Katdare, SP ;

Seddon, KR .

ORGANIC LETTERS, 2004, 6 (05) :707-710

[10] CYANATION OF AROMATIC HALIDES [J].

ELLIS, GP ;

ROMNEYALEXANDER, TM .

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

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