Malonamides have previously been identified as useful organic ligands for copper, lanthanides, and actinides. Here we describe the synthesis of two novel indolylmalonamides by a stepwise method. First, a scandium(III)-catalyzed indole addition to coumarin-3-carboxylate was performed to afford indolylchromanone-3-carboxylates in good yield. Next, a lanthanum(III)-catalyzed amidation was performed to afford the target indolylmalonamides. Additional routes and target malonamides are being explored. <br/> <br/>Simultaneously, two published malonamides were synthesized for NMR metal binding studies. The ligand was stirred with lanthanum chloride in ratios of 1:1, 2:1, and 3:1, solvent was removed, and the resulting complexes were analyzed by <sup>1</sup>H NMR. Comparison of the complex spectra to the spectrum of the unbound malonamide shows downfield shifts of the amide protons, as well as a slight shift of the phenol proton. Further studies with different metals, solvents, and solvent pHs are ongoing.

Synthesis of indolylmalonamides and analysis of their metal binding properties

253rd National Meeting (2017)

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