Synthesis of Di- and Tri-Substituted Imidazole-4-carboxylates via PBu3-Mediated [3+2] Cycloaddition

被引：4

作者：

Hsu, Mei-Yuan ^{[1
]}

Dietrich, Justin ^{[2
,3
]}

Hulme, Christopher ^{[2
,3
]}

Shaw, Arthur Y. ^{[2
,3
]}

机构：

[1] Tamkang Univ, Dept Chem, New Taipei City, Taiwan

[2] Univ Arizona, Coll Pharm, Dept Pharmacol & Toxicol, Tucson, AZ 85721 USA

[3] Univ Arizona, Oro Valley BIO5, Oro Valley, AZ USA

来源：

SYNTHETIC COMMUNICATIONS | 2013年 / 43卷 / 11期

关键词：

3+2] Cycloaddition; cyclo-dehydration; dehydrating agent; imidazole-4-carboxylate; 2-oxazolinone;

D O I：

10.1080/00397911.2011.644846

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Some new di- and trisubstituted imidazole-4-carboxylates were prepared from amidoacetic acids 3 in the present report. The key step to establish such imidazole-4-carboxylates stemmed from the PBu3-mediated [3+2] cycloaddition between in situ-generated 2-oxazolinone 4 and ethyl cyanoformate6. Our results indicated that trisubstituted imidazoles 7-20 were afforded in better yields than those of disubstituted imidazoles 21-27. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

引用

页码：1538 / 1542

页数：5

共 6 条

[1] Application of a novel [3+2] cycloaddition reaction to prepare substituted imidazoles and their use in the design of potent DFG-out allosteric B-Raf inhibitors [J].