No abstract

No abstract

No abstract

Novel oxospirobicyclic γ-butenolides containing barbiturate moiety have been synthesised by the Michael-addition of primary amines to dialkyl acetylenedicarboxylates followed by aldol-like reaction with alloxan derivatives, and then γ-lactonisation. Subsequent 1,4-addition of water and elimination of the amine group completes the sequence. This tandem reaction sequence represents a rapid and unprecedented route to the described biologically interesting molecules.

Multicomponent Tandem Synthesis of Oxospirobicyclic Butenolidobarbiturates.-The sequence of this new one-pot, multicomponent reaction involves a 1,4-Michael addition, aldol-like reaction, lactonization, 1,4-addition-elimination and an acid-base reaction and leads to biologically relevant oxospirocyclic compounds (IV), containing two different pharmacophoric subunits. Surprisingly, in some cases with alloxan (Id) as starting material, the hydroxy barbiturates (V) are obtained instead of spirocyclic butenolides. The formation of (V) provides clear-cut evidence for the existence of this type of intermediate in the reaction pathway. The protocol employed has some advantages over sequential multi-step procedures including superior atom economy, simplified work-up, and superior overall yields. -(TEIMOURI*, M. B.; ABBASI, T.; KHAVASI, H. R.; J.