Bromodimethylsulfonium bromide (BDMS): a useful reagent for conversion of aldoximes and primary amides to nitriles

被引：49

作者：

Yadav, Lal Dhar S. ^{[1
]}

Srivastava, Vishnu P. ^{[1
]}

Patel, Rajesh ^{[1
]}

机构：

[1] Univ Allahabad, Green Synth Lab, Dept Chem, Allahabad 211002, Uttar Pradesh, India

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 39期

关键词：

Bromodimethylsulfonium bromide (BDMS); Elimination; Aldoximes; Nitriles; Primary amides; Acetonitrile; ONE-POT SYNTHESIS; EFFICIENT BECKMANN REARRANGEMENT; PALLADIUM-CATALYZED CYANATION; HIGHLY EFFICIENT; SOLVENT-FREE; (BROMODIMETHYL)SULFONIUM BROMIDE; SYNTHETIC METHODOLOGIES; CONJUGATE HYDROTHIOCYANATION; CONVENIENT CONVERSION; OXIDATIVE CONVERSION;

D O I：

10.1016/j.tetlet.2009.07.100

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An operationally simple and high yielding procedure has been developed for the preparation of nitrites from aldoximes and primary amides using bromodimethylsulfonium bromide (BDMS) as a novel and efficient reagent in the absence of any added base or catalyst. The optimal protocol is applicable to access a wide range of cyano compounds including aromatic, heterocyclic, and aliphatic species. The conversion of aldoximes to nitriles takes place at room temperature in acetonitrile, whereas acetonitrile at reflux temperature is required for rapid conversion in the case of primary amides. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：5532 / 5535

页数：4

共 115 条

[11] Ketones to amides via a formal Beckmann rearrangement in 'one pot': a solvent-free reaction promoted by anhydrous oxalic acid. Possible analogy with the Schmidt reaction [J].

Chandrasekhar, S ;

Gopalaiah, K .

TETRAHEDRON LETTERS, 2003, 44 (40) :7437-7439

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

Chaudhari, SS ;

Akamanchi, KG .

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

[13] Bromodimethylsulfonium bromide (BDMS): A versatile reagent in organic synthesis [J].

Choudhury, Md Lokman Hakim .

SYNLETT, 2006, (10) :1619-1620

[14] CYANIDE SUBSTITUTION IN ARYL HALIDES BY COPPER(L) COMPLEXES DERIVED FROM FORMAMIDE AND FROM FORMALDEHYDE OXIME [J].

CONNOR, JA ;

GIBSON, D ;

PRICE, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (03) :619-621

[15] Mild and efficient method for the synthesis of nitriles [J].

Coskun, N .

SYNTHETIC COMMUNICATIONS, 2004, 34 (09) :1625-1630

[16] Studies on novel synthetic methodologies, part 67.: (Bromodimethyl)sulfonium bromide catalyzed one-pot synthesis of α-aminonitriles [J].

Das, B ;

Ramu, R ;

Ravikanth, B ;

Reddy, KR .

SYNTHESIS-STUTTGART, 2006, 9 (09) :1419-1422

[17] Bromination of alkenes and alkynes with (bromodimethyl)sulfonium bromide [J].

Das, Biswanath ;

Srinivas, Yallamalla ;

Sudhakar, Chittaluri ;

Ravikanth, Bornmena .

JOURNAL OF CHEMICAL RESEARCH-S, 2008, (04) :188-190

[18] An efficient synthesis of benzyl bromides from aromatic aldehydes using polymethylhydrosiloxane and (bromodimethyl)sulfonium bromide or N-bromosuccinimide [J].

Das, Biswanath ;

Srinivas, Yallamalla ;

Holla, Harish ;

Laxminarayana, Keetha ;

Narender, Ravirala .

TETRAHEDRON LETTERS, 2007, 48 (38) :6681-6683

[19] Efficient (bromodimethyl)sulfonium bromide mediated synthesis of benzimidazoles [J].

Das, Biswanath ;

Holla, Harish ;

Srinivas, Yallamalla .

TETRAHEDRON LETTERS, 2007, 48 (01) :61-64

[20] Studies on novel synthetic methodologies, part 81.: A rapid and efficient stereoselective synthesis of (Z)- and (E)-allyl bromides from Baylis-Hillman adducts using bromo(dimethyl)sulfonium bromide [J].

Das, Biswanath ;

Venkateswarlu, Kafta ;

Krishnaiah, Maddeboina ;

Holla, Harish ;

Majhi, Anjoy .

HELVETICA CHIMICA ACTA, 2006, 89 (07) :1417-1421

← 1 2 3 4 5 6 7 8 9 10 →