Gold-Catalyzed Unexpected Ring Transformation of Pyrimidodiazepine Derivatives

被引：8
|
作者：
Koo, Jaeyoung [1 ]
Kim, Jonghoon [1 ]
Park, Seung Bum [1 ,2 ]
机构：
[1] Seoul Natl Univ, Dept Biophys & Chem Biol, Seoul 08826, South Korea
[2] Seoul Natl Univ, Dept Chem, Seoul 08826, South Korea
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 02期
基金：
新加坡国家研究基金会;
关键词：
DIVERSITY; PROTEIN; STRATEGY; INHIBITORS; DISCOVERY; ROUTES;
D O I：
10.1021/acs.orglett.6b03520
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Pyrimidodiazepine derivatives underwent an unexpected gold-catalyzed retro-Mannich-type carbon-carbon bond cleavage and intramolecular nucleophilic cyclization. The pyrimidodiazepines bearing an alkyne moiety showed novel orthogonal reactivity in the presence of a gold catalyst, as opposed to the alkynophilicity that is commonly observed with gold catalysts. The ring transformation reaction of pyrimidodiazepines probably proceeds through an acyclic iminium intermediate. The potential of this synthetic method for the skeletal diversification of pyrimidine-containing macrocycles was also demonstrated.
引用
收藏
页码：344 / 347
页数：4
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