Intramolecular amidoselenation of N-alkenyl amides: formation of nitrogen heterocycles

A Toshimitsu, K Terao, S Uemura

Index: Toshimitsu, Akio; Terao, Keiji; Uemura, Sakae Journal of Organic Chemistry, 1986 , vol. 51, # 10 p. 1724 - 1729

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Citation Number: 81

Abstract

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, ...