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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 3
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Original Articles

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

, &
Pages 431-437 | Received 28 Apr 2011, Published online: 02 Nov 2012
 

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

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.

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