Solution-Phase Parallel Synthesis of a Multisubstituted Cyclic Imidate Library

被引：18

作者：

Mehta, Saurabh ^{[1
,2
]}

Waldo, Jesse P. ^{[1
]}

Neuenswander, Benjamin ^{[3
,4
]}

Lushington, Gerald H. ^{[3
,4
]}

Larock, Richard C. ^{[1
]}

机构：

[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA

[2] Delhi Technol Univ, Dept Appl Chem, Delhi 110042, India

[3] Univ Kansas, NIH, Ctr Excellence Chem Methodol, Lawrence, KS 66047 USA

[4] Univ Kansas, Lib Dev, Lawrence, KS 66047 USA

来源：

ACS COMBINATORIAL SCIENCE | 2013年 / 15卷 / 05期

基金：

美国国家卫生研究院;

关键词：

solution-phase; parallel synthesis; iodocyclization; cyclic imidates; iminolactones; palladium coupling; DRUG-DELIVERY REVIEWS; ELECTROPHILIC CYCLIZATION; EFFICIENT SYNTHESIS; ESTIMATE SOLUBILITY; DIVERSE LIBRARY; ARYL; 2,3-ALLENAMIDES; IMINOLACTONES; CONSTRUCTION; PERMEABILITY;

D O I：

10.1021/co3001605

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The solution-phase parallel synthesis of a diverse 71-member library of multisubstituted cyclic imidates is described. The key intermediates, 3-iodomethylene-containing cyclic imidates, are readily prepared in good to excellent yields by the palladium/copper-catalyzed cross-coupling of various o-iodobenzamides and terminal alkynes, followed by electrophilic cyclization with I-2. These cyclic imidates were further functionalized by palladium-catalyzed Suzuki-Miyaura, Sonogashira, carbonylative amidation, and Heck chemistry using sublibraries of commercially available building blocks.

引用

页码：247 / 254

页数：8

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