Abstract Furo [2, 3-b: 4, 5-c ']-1a,-[3, 2-b: 4, 5-c']-1b,-[2, 3-c: 4, 5-c ']-1c and-[3, 2-c: 4, 5-c'] dipyridine 1d were derived to the N-oxides 2a-d, N '-oxides 2′ b, 2′ c or N, N'-dioxide 3b-d by N-oxidation with m-chloroperbenzoic acid. Chlorination of these N-oxides, N′-oxide and N, N′-dioxides with phosphorus oxychloride afforded compounds chlorinated at the α- position (s) to the ring nitrogen 4a-d, 4′ c, 14b-d and 14′ b. Acetoxylation of N-oxides ...