Hydrothiolation and Intramolecular Cyclization Sequence for the Synthesis of 1,3-Oxathiine Frameworks

Abstract

1,3-Oxathiine frameworks can be prepared via the sequential addition and intramolecular cyclization of thiosalicylic acid onto alkynes. A substituent on the alkyne and the presence of a palladium catalyst can allow product regioselectivity control. This strategy is applicable to the synthesis of heterocycles comprising sulfur and oxygen atoms, namely 3,1-benzoxathiines, without any unwanted byproduct.

Key words

heterocycles - hydrothiolation - palladium - sequential reaction - alkynes - 3,1-benzoxathiines

• References


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• 18 The trans-vinyl sulfides 5c′ (see Supporting Information) were also transformed into 4j under the same reaction conditions of Equation 2
• 19 In this case, AIBN did not work as an appropriate promoter; 4j was obtained in 52% yield and unknown mixture of products was observed