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Fused bicyclic heterocycles with a bridgehead nitrogen atom is a structural scaffold present in various natural and unnatural bioactive compounds. Among these heterocycles, the pyrrolizidines, indolizidines and pyrroloazepines are important classes of alkaloids from the medicinal chemistry and chemical ecology point of views. 1 We disclosure herein our results concerning the formal aza-[3+2] and formal aza-[3+3] cycloaddition reactions of cyclic enaminones, including a chiral one, with maleic anhydride and N-aryl-maleimides, wherein pyrrolizidines, indolizidines and pyrroloazepines could be selectively obtained.

proceedings of the 14th brazilian meeting on organic synthesis proceedings

Synthesis of pyrrolizidines, indolizidines and pyrroloazepines through formal aza-[3+3] and aza-[3+2] cycloadditions of enaminones with maleic anhydride and maleimides