Intramolecular dehydrogenative C–S bond coupling of thioamides to form 1,3-benzothiazines under metal-free conditions

Abstract

A novel HTIB-promoted direct intramolecular dehydrogenative C–S bond coupling reaction of thioamides has been developed to provide 1,3-benzothiazine derivatives in good yields. The reaction proceeds smoothly to reach completion at room temperature within 1 min under metal-free conditions. This protocol provides a mild and efficient strategy for the synthesis of six-membered N,S-containing heterocycles. Preliminary mechanistic studies indicate that a spirocyclic intermediate might be involved.