Reaction of (Z)-5-(Bromomethylene)thiophen-2(5H)-one with Some Nucleophiles in Search for New Biofilm Inhibitors

Abstract

(Z)-5-(Bromomethylene)thiophen-2(5H)-one reacts in a Michael-type addition across the methylene side chain with nucleophiles followed by elimination of bromide. The reaction was done at room temperature and the yields were good. The aromatic sulfur substitution products showed potent activity as biofilm inhibitors.

GRAPHICAL ABSTRACT

Keywords:

• Biofilm
• biofilm inhibitors
• elimination
• Michael addition
• thiophenones

Notes

^a Z-isomer. From the ¹H NMR of the crude product, in some cases signals seem to come from minor amounts of the E-isomer.

^b Ring-opening reaction occurs; see text.

^c Ref. 6.