Selective access to sulfurated and selenated heterocycles by intramolecular cyclization of β-substituted sulfides and selenides

GRAPHICAL ABSTRACT

ABSTRACT

δ-Hydroxy- and δ-amino α-thio-esters, easily obtainable through S-alkylation of β-mercapto alcohols and β-amino thiols with bromo acetate, behave as suitable starting compounds to obtain various 2-hydroxy-1,4-oxathianes and (S)-3,4-dihydro-2H-1,4-thiazines via a reductive ring closure. Under similar conditions, selenated heterocycles are also synthesized.

KEYWORDS:

• 2-Hydroxy-1,4-oxathianes
• 3,4-dihydro-2H-1,4-thiazines
• 2-hydroxy-1,4-selenanes
• 3,4-dihydro-2H-1,4-selenazines
• ring closure