Issue 38, 2017

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

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

Supplementary files

Article information

Article type
Communication
Submitted
23 Aug 2017
Accepted
09 Sep 2017
First published
11 Sep 2017

Org. Biomol. Chem., 2017,15, 8013-8017

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

H. Wang, T. Shi, W. Gao, H. Zhang, Y. Wang, J. Li, Y. Hou, J. Chen, X. Peng and Z. Wang, Org. Biomol. Chem., 2017, 15, 8013 DOI: 10.1039/C7OB02101A

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