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

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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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Publication details

The article was received on 23 Aug 2017, accepted on 09 Sep 2017 and first published on 11 Sep 2017


Article type: Communication
DOI: 10.1039/C7OB02101A
Citation: Org. Biomol. Chem., 2017, Advance Article
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    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, Advance Article , DOI: 10.1039/C7OB02101A

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