Reductive dehalogenation of 4-halogenomethyl azetidin-2-one derivatives. Synthesis of (4-oxo-azetidin-2-yl)acetonitriles

Abstract

The stability of the β-lactam ring under reductive conditions was examined in order to find a selective method for the synthesis of (4-oxo-azetidin-2-yl)acetonitrile derivatives. Fifteen variously substituted 4-halogenomethyl-β-lactam derivatives were synthesised and dehalogenated by three reductive methods. It was found that both the substituents connected to the four-membered ring and to the halogenomethyl group, as well as the applied method have considerable influence on the ratio of the resulting ring-containing and ring-opened products. The best conditions have been defined to give – state products – in excellent yields.