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Double 1,4-addition of (thio)salicylamides/thiosalicylic acids with propiolate derivatives: a direct, general synthesis of diverse heterocyclic scaffolds†
Hui-Hong Wang,Tao Shi,Wei-Wei Gao,Hong-Hua Zhang,Yong-Qiang Wang,Jun-Fang Li,Yong-Sheng Hou,Jin-Hong Chen,Xue Peng
Organic & Biomolecular Chemistry Pub Date : 09/11/2017 00:00:00 , DOI:10.1039/C7OB02101A
Abstract

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.

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