Nucleophilic Ring Enlargement of 2-Substituted-3-isothiazolones to 1,3-Thiazin-4-ones

Abstract

1,3-Thiazin-4-ones 9 and 10 have been prepared from the corresponding isothiazolones 7 and 8 by a clean and smooth reaction with tertiary amines at room temperature. This rearrangement is attributed to the abstraction of a methine proton from the 2-position isothiazolone substituent, followed by ring enlargement through cleavage of the S-N bond.

Keywords:

• 3-Isothiazolones
• 1,3-Thiazin-4-ones
• Nucleophilic ring expansion
• Two phase reactions