Synthesis of 3,4-bis(2,5-dimethyl-3-thienyl)furan-2,5-dione from mucobromic acid

Abstract

Palladium catalyzed cross coupling between 2,5 dimethyl 3 thienylboronic and mucobromic acids under phase transfer catalysis (PTC) conditions gave the expected 3,4 bis(2,5 dimethyl 3 thienyl) 5 hydroxyfuran 2 one in 32% yield. The by product was 2,2´,5,5´ tetramethyl 3,3´ bithiophene. The oxidation of the obtained hemiacylal with potas sium permanganate under PTC conditions afforded 3,4 bis(2,5 dimethyl 3 thienyl)furan 2,5 dione in high yield.

A ‘chemically-gated’ photoresponsive compound as a visible detector for organophosphorus nerve agents

“…The ring-open isomer of the phenolic dithienylethene (1o) was synthesized by following the procedures published for the preparation of a similar compound.w 13 The synthesis is shown in Scheme 1 and involves the double Suzuki coupling of two known starting materials, 3,4-dibromo-furan-2,5-dione 15 and acid, 16 to produce an anhydride (3) bearing the required hexatriene. This anhydride is converted to the maleimide 1o in good yield by reacting it with o-hydroxyaniline.…”