Journal
MOLECULAR DIVERSITY
Volume 10, Issue 1, Pages 17-22Publisher
SPRINGER
DOI: 10.1007/s11030-006-8695-3
Keywords
imidazoles; multicomponent reaction; microwave; diversity; library synthesis; combinatorial chemistry
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Optimization of Radziszewski's four-component reaction employing a microwave-assisted protocol, led to a small library of 48 imidazoles with a success rate of 65% (conversion > 45%). All three diversity points of the four-component reaction were varied. Aromatic and aliphatic inputs were successfully implemented and mono-, di-, tri- and tetrasubstituted imidazoles with various substitution patterns were synthesized. Furthermore, unsymmetrical diketones could successfully be used which improved the intrinsic diversity of the method significantly. If the unsymmetrical diketone 1,2-phenylpropanedione (R-1 and R-2) was used two regioisomers were formed. Depending oil the type of amine (R-4) and aldehyde (R-3) applied, regioselectivity was modest to good. Based on these results, a reaction mechanism is proposed.
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