Macrocyclizations for Medicinal Chemistry: Synthesis of Druglike Macrocycles by High-Concentration Ullmann Coupling

被引：21

作者：

Collins, James C. ^{[1
]}

Farley, Kathleen A. ^{[2
]}

Limberakis, Chris ^{[2
]}

Liras, Spiros ^{[2
]}

Price, David ^{[2
]}

James, Keith ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[2] Pfizer Worldwide R&D, Groton, CT 06340 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 24期

关键词：

CATALYZED ARYLATION; N-ARYLATION; COPPER; VANCOMYCIN; IMIDAZOLES; PHENOLS; DESIGN; GREEN;

D O I：

10.1021/jo302089f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conditions have been identified for the efficient Ullmann macrocyclization of phenol and imidazole nucleophiles with aryl iodides at high reaction concentrations of up to 100 mM and using 5-10 mol % loading of an inexpensive copper catalyst. A range of substitution patterns and ring sizes are tolerated, and the method has been exemplified by the synthesis of a set of druglike macrocycles.

引用

页码：11079 / 11090

页数：12

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