N-bromosuccinimide/1,8-diazabicyclo[5.4.1]undec-7-ene combination: β-amination of chalcones via a tandem bromoamination/debromination sequence.
A one-pot cascade transformation of chalcones into β-imidoketones has been developed, in which NBS provides both electrophilic bromine and nucleophilic nitrogen sources, and DBU functions as a nucleophilic reagent to activate NBS to be a more electrophilic bromine species and to further remove the bromine of α-bromoketones. The whole process involves tandem bromoamination and debromination, which represents a unique example of preparing β-aminoketones by the reaction of chalcones with the NBS/DBU combination.
Department of Chemistry, Northeast Normal University, Changchun 130024, China.
Ying
Y
Wei
Shaoxia
S
Lin
Fushun
F
Liang
Jingping
J
Zhang
D000586:Amination; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry; D001974:Bromosuccinimide / Q000737:chemistry*; D002384:Catalysis; D047188:Chalcones / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; D047188:Chalcones; D006842:Hydrocarbons, Brominated; D001974:Bromosuccinimide