Reactions of Thioamides with Iminoiodinanes: An Approach toward 1,2-Thiazines, Thiophenes, and Sulfonylisothiazolines

Abstract

Transition metal-catalyzed and noncatalytic reactions of acrylic thioamides with N-sulfonyliminoiodinanes enabling the selective synthesis under mild conditions of a series of fully decorated S- and N,S-containing heterocycles are described. Fine-tuning of the thioamide structure allows selective preparation in good yields of ortho-fused thiophenes, 1,2-thiazines, and spiro-fused isothiazolines. A one-pot thermally induced rearrangement of sulfonylisothiazolines was discovered as a complementary route to thiophenes.