Termination of Mn(III)-based oxidative cyclizations by trapping with azide.
The radicals formed in Mn(III)-based oxidative free-radical cyclizations of beta-keto esters and malonate esters can be trapped with sodium azide and Mn(III) to give cyclic and bicyclic azides in 30-80% yield. Reduction of the azide gives bi- and tricyclic lactams. [reaction: see text]
Snider
Barry B
BB
Department of Chemistry, MS 015, Brandeis University, Waltham, MA 02454-9110, USA. snider@brandeis.edu
Duvall
Jeremy R
JR
D001386:Azides / Q000737:chemistry*; D003500:Cyclization; D004952:Esters / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis; D008345:Manganese / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction
D001386:Azides; D004952:Esters; D005609:Free Radicals; D007769:Lactams; D008345:Manganese