Intramolecular Amidoselenation of N-Alkenylamides: Formation of Nitrogen Heterocycles

Article abstract of DOI:10.1021/jo00360a017

The reaction of N-alkenylamides with benzeneselenenyl halides affords pyrrolidine or piperidine derivatives through the cyclization by a nitrogen atom of the amide group induced by the addition of a phenylseleno group to the double bond.The introduction of substituents into the carbon atom between the double bond and amide moiety facilitates the cyclization reaction.The effect of a halide ion of the selenenylating reagent is also significant, bromide generally giving the best result.The method can be applied for the preparation of bicyclic nitrogen heterocycles such as pyrrolizidine derivatives and thienamycin skeleton.