Solid-Phase Synthesis of Piperazinones via Disrupted Ugi Condensation

被引：8

作者：

Treder, Adam P. ^{[1
]}

Tremblay, Marie-Claude ^{[1
]}

Yudin, Andrei K. ^{[2
]}

Marsault, Eric ^{[1
]}

机构：

[1] Univ Sherbrooke, Inst Pharmacol Sherbrooke, Dept Pharmacol, Sherbrooke, PQ J1H SN4, Canada

[2] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 17期

关键词：

BACKBONE AMIDE LINKER; ON-RESIN CYCLIZATION; MULTICOMPONENT REACTIONS; SUPPORTED SYNTHESIS; CCR5; ANTAGONISTS; NATURAL-PRODUCTS; BAL STRATEGY; PEPTIDE; CHEMISTRY; INHIBITORS;

D O I：

10.1021/ol5023118

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first application of aziridine aldehyde dimers in solid-phase synthesis is reported. The solid-supported disrupted Ugi condensation between an aziridine aldehyde dimer, isonitrile, and backbone-anchored amino acids delivered N-acyl aziridine intermediates, which were reacted with nudeophiles to yield the corresponding piperazinones. Subsequent cleavage from the resin provided a diverse set of 2,3,6-trisubstituted piperazinones starting from various amino acids, aziridine aldehydes, and nucleophiles.

引用

页码：4674 / 4677

页数：4

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