108429-75-0Relevant academic research and scientific papers
Intramolecular Amidoselenation of N-Alkenylamides: Formation of Nitrogen Heterocycles
Toshimitsu, Akio,Terao, Keiji,Uemura, Sakae
, p. 1724 - 1729 (2007/10/02)
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.
Intramolecular Amidoselenation of N-Alkenyl Imidates to N-Heterocycles
Terao, Keiji,Toshimitsu, Akio,Uemura, Sakae
, p. 1837 - 1844 (2007/10/02)
The reactions of N-alkenyl imidates with benzeneselenenyl chloride and bromide in chloroform at ambient temperature afford pyrrolidine and piperidine derivatives having a phenylseleno moiety in good to excellent yields under neutral conditions.The key step of this new reaction consists of an intramolecular carbon-nitrogen bond formation and a simultaneous carbon-oxygen bond fission.
