Derivatives of 4-Hydroxy-6-Methyl-Pryan-2-one (Triacetic Lactone)

Acylation, using aliphatic dicarboxylic acid chlorides of triacetic lactone (1) has led to the formation of bispyran-2~nes of type (10. The bispyrones (Ila) and (lIb) on treatment with hydrochloric acid gave bispyran-4~nes (IVa) and (IVb) respectively. The action of methyl amine on (lIa,b) yielded the corresponding bispyridones (Va,b). Reactions of (1) with other electrophiIic reagents such as thionyl cWoride, Vilsmeyer formylation mixture (dimethyl formamide and phosphor­yl cWoride) and benzene diazonium chloride have resulted in the formation of (VIla), (VIlla) and (VlIIb) respectively. 3-Amino-derivatives (VlIId) and (VIlle) have also been prepared. The 3-position of (1) has been found out to be the exclusive site of electrophilic substitution reactions. The spectro­scopic data of the compounds has also been recorded.

Zeeshan Shah ,