Abstract
Free radical cyclization is rapidly becoming an important method for the synthesis of cyclic compounds. This review summarizes our recent studies on the synthesis of nitrogen-containing heterocycles by means of cyclization of N-alkenic carbamoylmethyl radicals which are generated from the corresponding α-haloamides by treatment with tributyltin hydride in the presence of azobis (isobutyronitrile) (AIBN) Ruthenium-catalyzed chlorine atom transfer cyclizations of α-chloro-α-thioacetamides have also been examined. These reactions are classified into several types of ring closures including relatively difficult 4-exo-trig and 5-endo-trig cyclizations which provide β- and γ-lactams, respectively. Applications of the method to the synthesis of natural products are also presented.
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