Synthesis of allylic thiocyanates and novel 1,3-thiazin-4-ones from 2-(bromomethyl)alkenoates and S-nucleophiles in aqueous medium

被引：44
作者：
Sa, Marcus M. [1 ]
Fernandes, Luciano [1 ]
Ferreira, Misael [1 ]
Bortoluzzi, Adailton J. [1 ]
机构：
[1] Univ Fed Santa Catarina, Dept Quim, BR-88040900 Florianopolis, SC, Brazil
来源：
TETRAHEDRON LETTERS | 2008年 / 49卷 / 07期
关键词：
allylic thiocyanate; 1,3-thiazinone; 2-(bromomethyl)alkenoate; S-nucleophiles; aqueous solvent;
D O I：
10.1016/j.tetlet.2007.12.029
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Allylic thiocyanates and novel heterocycles containing the 1,3-thiazin-4-one core are easily obtained in high yields and mild conditions by nucleophilic displacement of 2-(bromomethyl)alkenoates (derived from Morita - Baylis - Hillman adducts) with sulphur-centred nucleophiles in aqueous acetone at 25 degrees C. Treatment of allylic bromides with NaSCN gave the corresponding (Z)-2-(thiocyanomethyl)alkenoates, while the reaction with thiourea followed by a basic work-up selectively produced (5Z)-2-amino-5-arylidene-1,3-thiazin-4-ones. The structural assignments were confirmed by X-ray diffraction analysis. (c) 2007 Elsevier Ltd. All rights reserved.
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收藏
页码：1228 / 1232
页数：5
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