Microwave-assisted fluorous synthesis of a 1,4-benzodiazepine-2,5-dione library.
Fluorous displaceable linker-facilitated synthesis of 1,4-benzodiazepine-2,5-dione library has been developed. Perfluorooctanesulfonyl protected 4-hydroxy benzaldehydes were used as the limiting agent for Ugi four-component reactions to form condensed products. Postcondensation reactions of the Ugi products generated 1,4-benzodiazepine-2,5-dione ring skeleton. Microwave-assisted Suzuki coupling reactions removed the fluorous tag and introduced biaryl functionality to the benzodiazepine ring. The library scaffold has four points of substitution diversities. The fluorous tag facilitated the intermediate purifications using fluorous solid-phase extraction (F-SPE) and had no negative impact on the reactivity of the Ugi reactions and postcondensation reactions.
Liu
Aifeng
A
School of Pharmaceutical Sciences, Shandong University, Jinan, China.
Zhou
Hongyu
H
Su
Gaoxing
G
Zhang
Wei
W
Yan
Bing
B
D001570:Benzodiazepinones / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D008872:Microwaves; D015394:Molecular Structure; D054852:Small Molecule Libraries; D013237:Stereoisomerism
D001570:Benzodiazepinones; D054852:Small Molecule Libraries