A simple one-pot procedure for the direct conversion of alcohols into alkyl nitriles using TsIm

被引：39

作者：

Rad, Mohammad Navid Soltani ^{[1
]}

Khalafi-Nezhad, Ali

Behrouz, Somayeh

Faghihi, Mohammad All

机构：

[1] Shiraz Univ Technol, Fac Basic Sci, Dept Chem, Shiraz 71555 313, Iran

[2] Shiraz Univ, Coll Sci, Dept Chem, Shiraz 71454, Iran

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 38期

关键词：

nitrite; alcohol; N-(p-toluenesulfonyl)imidazole (TsIm); triethylamine (TEA); tetrabutylammonium iodide (TBAI);

D O I：

10.1016/j.tetlet.2007.07.091

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient and efficient one-pot preparation of nitriles from alcohols using N-(p-toluenesulfonyl)imidazole (TsIm) is described. In this method, treatment of alcohols with a mixture of NaCN, TsIm and triethylamine in the presence of catalytic amounts of tetra-n-butylammonium iodide (TBAI) in refluxing DMF furnishes the corresponding alkyl nitriles in good yields. This methodology is highly efficient for various structurally diverse alcohols with selectivity for ROH: 1 degrees > 2 degrees > 3 degrees. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：6779 / 6784

页数：6

共 76 条

[1] PREPARATION OF UNSATURATED NITRILES BY THE MODIFICATION OF MITSUNOBU-WILK PROCEDURE .2. CARBON ELONGATION OF BETA-ACETYLENIC ALCOHOLS
AESA, MC
BAAN, G
NOVAK, L
SZANTAY, C
[J]. SYNTHETIC COMMUNICATIONS, 1995, 25 (17) : 2575 - 2578
[2] Direct oxidative conversion of aldehydes to nitriles using IBX in aqueous ammonia
Arote, Nitin D.
Bhalerao, Dinesh S.
Akamanchi, Krishnacharya G.
[J]. TETRAHEDRON LETTERS, 2007, 48 (21) : 3651 - 3653
[3] Highly convenient, one-pot synthesis of nitriles from aldehydes using the NH2OH•HCl/NaI/MeCN system
Ballini, R
Fiorini, D
Palmieri, A
[J]. SYNLETT, 2003, (12) : 1841 - 1843
[4] Organic reactions in water: Highly rapid CAN mediated one-pot synthesis of nitriles from aldehydes under mild conditions
Bandgar, BP
Makone, SS
[J]. SYNLETT, 2003, (02) : 262 - 264
[5] Biogegrain R., 1975, TETRAHEDRON LETT, V30, P2529
[6] BOGDAN KW, 1993, SYNTHETIC COMMUN, V23, P2481
[7] Organic azides:: An exploding diversity of a unique class of compounds
Bräse, S
Gil, C
Knepper, K
Zimmermann, V
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) : 5188 - 5240
[8] SUGARS WITH POTENTIAL ANTIVIRAL ACTIVITY .I. CONVERSION OF HYDROXY COMPOUNDS TO NITRILES
BRETT, D
DOWNIE, IM
LEE, JB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (03) : 855 - &
[9] Buehler C.A., 1977, SURVEY ORGANIC SYNTH, V2
[10] A SIMPLE ONE-POT SYNTHESIS OF NITRILES FROM ALCOHOLS
CAMPS, F
GASOL, V
GUERRERO, A
[J]. SYNTHETIC COMMUNICATIONS, 1988, 18 (04) : 445 - 452

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