Solution phase synthesis of a library of tetrasubstituted pyrrole amides

被引：26

作者：

Bianchi, Ivana ^{[1
]}

Forlani, Roberto ^{[1
]}

Minetto, Giacomo ^{[1
]}

Peretto, Ilaria ^{[1
]}

Regalia, Nickolas ^{[1
]}

Taddei, Maurizio ^{[1
]}

Raveglia, Luca F. ^{[1
]}

机构：

[1] NiKem Res, I-20021 Milan, Italy

来源：

JOURNAL OF COMBINATORIAL CHEMISTRY | 2006年 / 8卷 / 04期

关键词：

D O I：

10.1021/cc060008q

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

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.

引用

页码：491 / 499

页数：9

共 28 条

[1] PYRIDINIUM CHLOROCHROMATE - AN IMPROVED METHOD FOR ITS SYNTHESIS AND USE OF ANHYDROUS ACETIC-ACID AS CATALYST FOR OXIDATION REACTIONS [J].