Structurally diverse arene-fused ten-membered lactams accessed via hydrolytic imidazoline ring expansion

被引:29
作者
Sapegin, Alexander [1 ]
Osipyan, Angelina [1 ]
Krasavin, Mikhail [1 ]
机构
[1] St Petersburg State Univ, Inst Chem, 26 Univ Skii Prospekt, Peterhof 198504, Russia
基金
俄罗斯科学基金会;
关键词
ORIENTED SYNTHESIS; DISCOVERY; STRATEGY; 2-IMIDAZOLINES; INHIBITORS; ARYLATION; PANEL;
D O I
10.1039/c7ob00535k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Imidazoline-fused [1,4] oxazepines (prepared in two simple steps from methyl 2-hydroxyaroates, ethylene diamine and bis- electrophilic aromatics) undergo a facile, good-yielding hydrolytic imidazoline ring expansion (HIRE) upon N-alkylation and treatment with aqueous K2CO3. The resulting arene-fused ten-membered lactams significantly add to the contemporary arsenal of smallmolecule scaffolds where medium-sized ring systems are severely underrepresented.
引用
收藏
页码:2906 / 2909
页数:4
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