2azetidinone

2-Azetidinone, also known as azetidin-2-one, is the smallest member of the beta-lactam family. It features a four-membered ring containing one nitrogen atom and a carbonyl group that is part of the ring, creating a strained cyclic amide (lactam). The unsubstituted parent compound serves primarily as a building block in medicinal chemistry and synthesis.

IUPAC naming places the carbonyl at position 2 on the azetidine ring, hence azetidin-2-one. The ring’s strain affects its reactivity, making the beta-lactam core prone to ring opening by acids, bases, or nucleophiles. Substituents on nitrogen or carbon can modulate stability and reactivity.

Preparation methods include cycloaddition approaches such as the Staudinger [2+2] cycloaddition of imines with ketenes to give azetidin-2-ones, and ring-closure syntheses from suitable amino carbonyl precursors. Because of their inherent reactivity, many practical applications focus on azetidinone derivatives rather than the parent compound.

Although not itself an antibiotic, the azetidinone scaffold is a core motif in many beta-lactam antibiotics, such as penicillins and cephalosporins, where the ring is part of a larger fused system. Researchers explore azetidinones as versatile starting points for creating drugs, agrochemicals, and other biologically active compounds.