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.

引用

页码：1228 / 1232

页数：5

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