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
收藏
页码：1335 / 1339
页数：5
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