A new synthesis of 4H-1-benzothiopyran-4-ones using (trimethylsilyl)methylenetriphenylphosphorane

The reaction of silyl ester of S-acyl(aroyl) thiosalicylic acids 3 with (trimethylsilyl)methylenetriphenylphosphorane 4 in step wise fashion leads to the acylphosphoranes 7, which subsequently undergo intramolecular Wittig cyclization on the thiolester carbonyl to afford the 4H-1-benzothiopyran-4-ones 8 in good to excellent yields. (C) 2001 Elsevier Science Ltd. All rights reserved.