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
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
收藏
页码:6088 / 6091
页数:4
相关论文
共 44 条
[31]   Ionic liquid as reagent.: A green procedure for the regioselective conversion of epoxides to vicinal-halohydrins using [AcMIm]X under catalyst- and solvent-free conditions [J].
Ranu, BC ;
Banerjee, S .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (11) :4517-4519
[32]   Ionic liquid promoted interrupted Feist-Benary reaction with high diastereoselectivity [J].
Ranu, Brindaban C. ;
Adak, Laksmikanta ;
Banerjee, Subhash .
TETRAHEDRON LETTERS, 2008, 49 (31) :4613-4617
[33]   Catalysis by ionic liquids: Significant rate acceleration with the use of [pmIm]Br in the three-component synthesis of dithiocarbamates [J].
Ranu, Brindaban C. ;
Saha, Amit ;
Banerjee, Subhash .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (03) :519-523
[34]   Efficient regio- and stereo-selective cleavage of aziridines and epoxides using an ionic liquid as reagent and reaction medium [J].
Ranu, Brindaban C. ;
Adak, Laksmikanta ;
Banerjee, Subhash .
CANADIAN JOURNAL OF CHEMISTRY, 2007, 85 (05) :366-371
[35]   Ionic liquid as catalyst and solvent: the remarkable effect of a basic ionic liquid, [bmIm]OH on Michael addition and alkylation of active methylene compounds [J].
Ranu, Brindaban C. ;
Banerjee, Subhash ;
Jana, Ranjan .
TETRAHEDRON, 2007, 63 (03) :776-782
[36]   Formation of ε-caprolactam via catalytic Beckmann rearrangement using P2O5 in ionic liquids [J].
Ren, RX ;
Zueva, LD ;
Ou, W .
TETRAHEDRON LETTERS, 2001, 42 (48) :8441-8443
[37]  
ROGERS RD, 2002, IONIC LIQUIDS IND AP, P474
[38]   Synthesis and structure-activity relationships of new benzodioxinic lactones as potential anticancer drugs [J].
Romero, Manel ;
Renard, Pierre ;
Caignard, Daniel-Henry ;
Atassi, Ghanen ;
Solans, Xavier ;
Constans, Pere ;
Bailly, Christian ;
Pujol, Maria Dolors .
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (02) :294-307
[39]   Remarkable influence of substituent in ionic liquid in control of reaction: simple, efficient and hazardous organic solvent free procedure for the synthesis of 2-aryl benzimidazoles promoted by ionic liquid, [pmim]BF4 [J].
Saha, Debasree ;
Saha, Amit ;
Ranu, Brindaban C. .
GREEN CHEMISTRY, 2009, 11 (05) :733-737
[40]   Efficient Beckmann rearrangement and dehydration of oximes via phosphonate intermediates [J].
Sardarian, A. R. ;
Shahsavari-Fard, Z. ;
Shahsavari, H. R. ;
Ebrahimi, Z. .
TETRAHEDRON LETTERS, 2007, 48 (14) :2639-2643