N-(2-formyl-1-methylimidazol-4-yl)-2,2-dimethylpropanamide: a versatile reagent for preparing imidazole-amine ligands with variable second-coordination spheres |
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Authors: | Lionel E CheruzelJinlan Cui Mark S MashutaCraig A Grapperhaus Robert M Buchanan |
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Institution: | Department of Chemistry, University of Louisville, Louisville, KY 40292, United States |
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Abstract: | Two synthetic pathways to N-(2-formyl-1-methylimidazol-4-yl)-2,2-dimethylpropanamide from 1-methyl-2-carboxaldehyde are described. The reagent serves as a useful synthon for reductive amination reactions with primary and secondary amines in the presence of sodium cyanoborohydride to yield a series of ligands with second coordination sphere functional groups. Protocols for the syntheses of related imidazole synthons functionalized in the 4-position with amino acids, Schiff bases, and other amides are also reported. |
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Keywords: | Amide Imidazole Nitroimidazole Non-covalent interactions |
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