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Synthesis of highly substituted 5-(trifluoromethyl)ketoimidazoles using a mixed-solid/solution phase motif.

B C Hamper·K D Jerome·G Yalamanchili·D M Walker·R C Chott·D A Mischke
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Abstract

Using a combination of solid phase synthesis for the preparation of N-substituted-N-acylglycines 7 followed by solution-phase ring transformation of trifluoromethylacyl munchnone intermediate 8, a library of 200 trisubstituted-5-trifluoromethylketo (TFMK) imidazoles 9 was prepared. In a sublibrary, bromoacetate resin 4 was treated with 5 amines in parallel to give N-substituted glycines 5 followed by acylation with 12 acid chlorides to provide, upon cleavage from the resin, 60 individual N-substituted-N-acylglycines 7. The glycines 7 were converted to munchnones 8 by treatment with trifluoroacetic anhydride followed by reaction with benzamidine to give trisubstituted-5-TFMK-imidazoles 9. The structural content of the library was analyzed using PlateView of the LCMS results, and individual members were isolated by automated preparative LCMS.

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Databases as TopicGlycineImidazolesIndicators and ReagentsKetonesModels, MolecularResins, PlantJournal Article

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B C Hamper, K D Jerome, G Yalamanchili, D M Walker, R C Chott, D A Mischke. 2000. Synthesis of highly substituted 5-(trifluoromethyl)ketoimidazoles using a mixed-solid/solution phase motif.. https://doi.org/10.1002/(sici)1097-0290(200024)71%3A1%3C28%3A%3Aaid-bit5%3E3.0.co%3B2-f

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