55212-09-4Relevant articles and documents
One-pot synthesis of benzo[e]1,4-oxathiepin-5-ones under solvent-free condition via self-promoted thiolysis of 1,2-epoxides
Fringuelli, Francesco,Pizzo, Ferdinando,Tortoioli, Simone,Vaccaro, Luigi
, p. 8780 - 8785 (2004)
Under solvent-free conditions, thiosalicylic acid (2) efficiently self-promotes the thiolysis of 1,2-epoxides 1, anti-stereoselectively and generally totally β-regioselectively. The resulting β-hydroxysulfide products 3 have been obtained in very good yields. Benzo[e]1,4-oxathiepin-5-ones 4 have been easily prepared in a regio- and diasteroselective manner and in satisfactory yields under SFC by a one-pot protocol including nucleophilic ring opening of 1,2-epoxides 1 by thiosalicylic acid (2) and thermally induced lactonization of β-hydroxy arylsulfides 3. Solvent-free condition and the absence of any catalyst make this procedure atom-economical and environmentally friendly.
