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.

Bianchi, R., Forlani, R., Minetto, G., Peretto, I., Regalia, M., Taddei, M., et al. (2006). Solution Phase Synthesis of a Library of Tetrasubstituted Pyrrole Amides. JOURNAL OF COMBINATORIAL CHEMISTRY, 8(4), 491-499 [10.1021/cc060008q].

Solution Phase Synthesis of a Library of Tetrasubstituted Pyrrole Amides

Minetto, Giacomo;Taddei, Maurizio;
2006-01-01

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.
2006
Bianchi, R., Forlani, R., Minetto, G., Peretto, I., Regalia, M., Taddei, M., et al. (2006). Solution Phase Synthesis of a Library of Tetrasubstituted Pyrrole Amides. JOURNAL OF COMBINATORIAL CHEMISTRY, 8(4), 491-499 [10.1021/cc060008q].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11365/2693
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