Double 1,4-addition of (thio)salicylamides/thiosalicylic acids with propiolate derivatives: a direct, general synthesis of diverse heterocyclic scaffolds,Organic & Biomolecular Chemistry

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Double 1,4-addition of (thio)salicylamides/thiosalicylic acids with propiolate derivatives: a direct, general synthesis of diverse heterocyclic scaffolds
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2017-09-11 00:00:00 , DOI: 10.1039/c7ob02101a
Hui-Hong Wang _{1,

2,

3,

4} , Tao Shi _{1,

2,

3,

4} , Wei-Wei Gao _{1,

2,

3,

4} , Hong-Hua Zhang _{1,

2,

3,

4} , Yong-Qiang Wang _{1,

2,

3,

4} , Jun-Fang Li _{1,

2,

3,

4} , Yong-Sheng Hou _{1,

2,

3,

4} , Jin-Hong Chen _{1,

2,

3,

4} , Xue Peng _{1,

2,

3,

4} , Zhen Wang _{1,

2,

3,

4,

5}

Affiliation

A simple and practical ring-closure procedure to prepare a range of diverse heterocycles has been developed. In this transformation, a variety of substituted (thio)salicylamides and thiosalicylic acids undergo a double 1,4-addition reaction with propiolate derivatives in the presence of an inorganic base (K₃PO₄), as a result benzothiazinones, benzoxazinones and benzoxathiinones were prepared in good to excellent yields, respectively, even in gram scales. In addition, further transformation towards more complex structures and oxicam drug analogues has also been successfully carried out.

中文翻译：

（硫代）水杨酰胺/硫代水杨酸与丙酸酯衍生物的双1,4-加成：多种杂环骨架的直接合成

已经开发了一种简单实用的闭环方法来制备一系列不同的杂环。在该转化中，在无机碱（K ₃ PO ₄）存在下，各种取代的（硫代）水杨酰胺和硫代水杨酸与丙酸酯衍生物进行双1,4-加成反应，结果苯并噻嗪酮，苯并恶嗪酮和苯并噻吩并酮为即使以克为单位，也可以分别以良好或优异的收率制备。另外，还已经成功地进行了向更复杂结构和奥昔康药物类似物的进一步转化。

更新日期：2017-09-18

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