Synthesis and reactions of 3-arylidene-5-aryl 2 [3H] furanoses

ABSTRACT

Continuation of our work on 2- furanones [1] we are going to discuss here the effect of nucleophilicity of different reagents toward 3- arylidene -2-furanones [IIb,d,f,g]. 3- Arylidene -2[3H]-furanones [IIa-g] have been prepared via Perkin's [2,3]condensation of the corresponding beta-aroyl propionic acid [la, b] with aromatic aldehydes namely, benzaldehyde, m- and p- tolualdehyde, m-bromobenzaldehyde and / or salicylaldehyde. Beta- Aroyl propionic acids [Ia, b] used in this research have been prepared via Friedel- Craft's acylation reaction of phenanthrene [in nitrobenzene as solvent] and / or p- bromobenzene [as a reactant and solvent] with succinic anhydride in the presence of anhydrous aluminium chloride [scheme 1]