Nitrones and oxaziridines. XXXI. Synthesis of some bicyclic 1-pyrroline 1-oxides

Abstract

The bicyclic 1-pyrroline 1-oxides (10), (11) and (13) have been prepared by reductive cyclization of the respective γ-nitro ketones (3),(4) and (6). Reduction of nitro ketone (2a) gave the unstable nitrone (7), which underwent dimerization to compound (8). Nitro ketones (2b,c,d) and (5) were also prepared. The pyrroline (14) was also a product of the reduction of nitro ketone (6) and was characterized as the enamide (15).