Double 1, 4-addition of (thio)salicylamides/thiosalicylic acids with propiolate derivatives: a direct, general synthesis of diverse heterocyclic scaffolds. Issue 38 (18th September 2017)

• Record Type: Journal Article
• Authors: Wang, Hui-Hong; Shi, Tao; Gao, Wei-Wei; Zhang, Hong-Hua; Wang, Yong-Qiang; Li, Jun-Fang; Hou, Yong-Sheng; Chen, Jin-Hong; Peng, Xue; Wang, Zhen
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 38(2017)
• Page Start: 8013
• Page End: 8017
• Publication Date: 2017-09-18
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob02101a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A simple and practical ring-closure procedure to prepare a range of diverse heterocycles has been developed. 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 (K3 PO4 ), 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.