Convenient Synthesis of 2,4-Disubstituted Tetrahydrothiophenes from Mannich's Adducts

Abstract

Ammonium salts of β-functionalized allylic amines 1 were successfully employed as electrophilic agents with functional thiols. The obtained intermediate 2 underwent intramolecular cyclization in the presence of potassium tert-butoxide to afford 2,4-disubstituted tetrahydrothiophenes 3.

Keywords:

• Mannich's adduct
• mercaptoacetonitrile
• methyl mercaptoacetate
• tetrahydrothiophene

Notes

^a Yields obtained after column chromatography.

^b Yields obtained with respect to products 2.