An easy access to functionalized allyl dithiocarbamates from Baylis-Hillman adducts in water

被引：47

作者：

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

Patel, Rajesh ^{[1
]}

Srivastava, Vishnu P. ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 12期

关键词：

Baylis-Hillman adducts; Stereoselective synthesis; Dithiocarbamates; Nucleophilic displacement; 1,3-Thiazines; Green procedure; ONE-POT SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; FACILE SYNTHESIS; AQUEOUS-MEDIA; CONJUGATE HYDROTHIOCYANATION; ANTIFUNGAL ACTIVITY; CATALYZED SYNTHESIS; CARBONYL-COMPOUNDS; ORGANIC-REACTIONS; IONIC LIQUIDS;

D O I：

10.1016/j.tetlet.2009.01.023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and direct highly stereoselective synthesis of [E]- and [Z]-allyl dithiocarbamates has been accomplished from acetates of Baylis-Hillman (BH) adducts in catalyst-free one-pot three-component coupling reactions of carbon disulfide and amine in water under a mild and green procedure with high yields. The reaction pathway involves the nucleophilic displacement (SN2') of BH acetates by dithiocarbamate anions. The utility of these allyl dithiocarbamates has also been demonstrated in heterocyclic chemistry. (C) 2009 Elsevier Science. All rights reserved (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：1335 / 1339

页数：5

共 100 条

[1]

[Anonymous], J SULFUR CHEM

[2]

[Anonymous], [No title captured], Patent No. 3743669

[3]

[Anonymous], 1981, SYNTHESIS

[4]

APSIMON J, 1988, TOTAL SYNTHESIS NATU, V8, P102

[5] One-pot synthesis of dithiocarbamates accelerated in water [J].

Azizi, N ;

Aryanasab, F ;

Torkiyan, L ;

Ziyaei, A ;

Saidi, MR .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (09) :3634-3635

[6] Waste-free and environment-friendly uncatalyzed synthesis of dithiocarbamates under solvent-free conditions [J].

Azizi, Naimedin ;

Ebrahimi, Forogh ;

Aakbari, Elham ;

Aryanasab, Fezzeh ;

Saidi, Mohammad R. .

SYNLETT, 2007, (18) :2797-2800

[7] A simple and novel eco-friendly process for the one-pot synthesis of dithiocarbamates from amines, carbon disulfide, and epoxides [J].

Azizi, Najmedin ;

Pourhasan, Bahram ;

Aryanasab, Fezzeh ;

Saidi, Mohammad R. .

SYNLETT, 2007, (08) :1239-1242

[8] Straightforward and highly efficient catalyst-free one-pot synthesis of dithiocarbamates under solvent-free conditions [J].

Azizi, Najmedin ;

Aryanasab, Fezzeh ;

Saidi, Mohammad R. .

ORGANIC LETTERS, 2006, 8 (23) :5275-5277

[9]

BAKUZIS P, 1978, TETRAHEDRON LETT, P2371

[10] THE INVENTION OF CHEMICAL-REACTIONS - THE LAST 5 YEARS [J].

BARTON, DHR .

TETRAHEDRON, 1992, 48 (13) :2529-2544

← 1 2 3 4 5 6 7 8 9 10 →