Synthesis of N-H Bearing Imidazolidinones and Dihydroimidazolones Using Aza-Heck Cyclizations

被引：36

作者：

Xu, Feiyang ^{[1
]}

Shuler, Scott A. ^{[1
]}

Watson, Donald A. ^{[1
]}

机构：

[1] Univ Delaware, Dept Chem & Biochem, Newark, DE 19716 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 37期

关键词：

aza-Heck reaction; catalysis; dihydroimidazolones; imidazolidinones; palladium; KETONE O-PENTAFLUOROBENZOYLOXIMES; PALLADIUM-CATALYZED CYCLIZATION; NK1 SELECTIVE ANTAGONISTS; II RECEPTOR ANTAGONISTS; CYCLIC UREA DERIVATIVES; ALKENE CARBOAMINATION; OXIME ESTERS; EFFICIENT SYNTHESIS; RING-SYSTEMS; POTENT;

D O I：

10.1002/anie.201806295

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of unsaturated, unprotected imidazolidinones via an aza-Heck reaction is described. This palladium-catalyzed process allows for the cyclization of N-phenoxy ureas onto pendant alkenes. The reaction has broad functional group tolerance, can be applied to complex ring topologies, and can be used to directly prepare mono- and bis-unprotected imidazolidinones. By addition of Bu4NI, dihydroimidazolones can be accessed from the same starting materials. Improved conditions for preparing unsaturated, unprotected lactams are also reported.

引用

页码：12081 / 12085

页数：5

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