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  • Title: Solution phase synthesis of a library of tetrasubstituted pyrrole amides.
    Author: Bianchi I, Forlani R, Minetto G, Peretto I, Regalia N, Taddei M, Raveglia LF.
    Journal: J Comb Chem; 2006; 8(4):491-9. PubMed ID: 16827560.
    Abstract:
    An efficient strategy for the solution-phase parallel synthesis of a library of pyrrole-amides is described. Key reactions include functional homologation of beta-ketoesters with a set of aldehydes followed by oxidation to produce a series of differently substituted 1,4-dicarbonyl compounds. Rapid cyclization using a microwave-assisted Paal-Knorr reaction provided a set of 24 pyrrole esters that were further functionalized through a trimethylaluminum-mediated aminolysis to obtain a larger library of 288 diverse pyrrole-3-amides. The tetrasubstitution allows a good exploration of the chemical space around the central pyrrole core. The last step was entirely automated with a Bohdan Myriad personal synthesizer.
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