Efficient library synthesis of imidazoles using a multicomponent reaction and microwave irradiation
| Autor: | B. J. Van Steen, Marinus B. Groen, Rob F. Schmitz, Edith Gelens, Leo A. J. M. Sliedregt, Rob Leurs, F. J. J. De Kanter, Chris G. Kruse, Romano V. A. Orru |
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| Přispěvatelé: | Organic Chemistry, Medicinal chemistry |
| Jazyk: | angličtina |
| Rok vydání: | 2006 |
| Předmět: |
Reaction mechanism
Aldehyde Catalysis Inorganic Chemistry Drug Discovery Structural isomer Organic chemistry Combinatorial Chemistry Techniques Physical and Theoretical Chemistry Microwaves Molecular Biology Diketone chemistry.chemical_classification Aldehydes Molecular Structure Chemistry Organic Chemistry Imidazoles Regioselectivity General Medicine Ketones Combinatorial chemistry Microwave irradiation Amine gas treating SDG 6 - Clean Water and Sanitation Information Systems |
| Zdroj: | Gelens, E, De Kanter, F J J, Schmitz, R F, Sliedregt, L A, Van Steen, B J, Kruse, C G, Leurs, R, Groen, M B & Orru, R V A 2006, ' Efficient library synthesis of imidazoles using a multicomponent reaction and microwave irradiation ', Molecular Diversity, vol. 10, no. 1, pp. 17-22 . https://doi.org/10.1007/s11030-006-8695-3 Molecular Diversity, 10(1), 17-22. Springer Netherlands |
| ISSN: | 1381-1991 |
| DOI: | 10.1007/s11030-006-8695-3 |
| Popis: | 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 (R1 and R2) was used two regioisomers were formed. Depending on the type of amine (R4) and aldehyde (R3) applied, regioselectivity was modest to good. Based on these results, a reaction mechanism is proposed. |
| Databáze: | OpenAIRE |
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