A SIMPLE AND PRACTICAL SYNTHESIS OF 2-AMINOIMIDAZOLES

被引：127

作者：

LITTLE, TL ^{[1
]}

WEBBER, SE ^{[1
]}

机构：

[1] AGOURON PHARMACEUT INC, SAN DIEGO, CA 92121 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 24期

关键词：

D O I：

10.1021/jo00103a021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new and simple two-step procedure to synthesize 2-aminoimidazoles (2-AI's) from readily available materials has been developed. The cyclization reaction of alpha-halo ketones and N-acetylguanidine in acetonitrile (MeCN) at reflux, or in dimethylformamide (DMF) at ambient temperature, gives 4(5)-substituted and 4,5-disubstituted N-(1H-imidazol-2-yl)acetamides, which are then hydrolyzed to their respective 2-AI's. In general, the purified products were isolated in good yields. We have prepared several examples and have demonstrated the usefulness of this method by its application in the total synthesis of 8, an interesting histamine analog, and oroidin, 15, a marine natural product isolated from various sponges.

引用

页码：7299 / 7305

页数：7

共 59 条

[51] MONONUCLEAR HETEROCYCLIC REARRANGEMENTS .6. CONVERSION OF 1,2,4-OXADIAZOLES INTO IMIDAZOLES [J].