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β-LACTAM REARRANGEMENTS INTO FIVE-MEMBERED HETEROCYCLES

Tonko Drazic, Marin Roje
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Abstract


β-Lactams are compounds of great importance in both medicinal chemistry and as building blocks for the synthesis of different types of biologically relevant compounds. Among other transformations, β-lactams can easily be rearranged into five-membered heterocycles. The rearrangement occurs by cleavage of any of four β-lactam bonds. The type of final five-membered ring mainly depends on the side chain groups of starting β-lactam, as well as reaction conditions. Furthermore, rearrangement reactions are often stereoselective, with product rings retaining the stereochemistry of β-lactams. The ability of β-lactams to form a variety of diversely decorated five-membered heterocycles, often in stereoselective fashion, makes this class of compounds attractive synthons in organic chemistry. This review covers the progress in the field within last ten years.


Keywords


hydantoin; imidazolidinone; imidazolidinethione; imidazolone; β-lactam; pyrrolidinone; thiohydantoin; transformation

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