One-Pot Synthesis of Polysubstituted 3-Amino-2-oxo-2,7-dihydro-1H-azepines

被引：1

作者：

Liao, Shengrong ^{[1
]}

Qin, Chun ^{[1
]}

Yao, Peifen ^{[2
]}

Li, Jinsheng ^{[1
]}

Zhou, Xuefeng ^{[1
]}

Wang, Junfeng ^{[1
]}

Huang, Zhishu ^{[2
]}

Liu, Yonghong ^{[1
]}

机构：

[1] Chinese Acad Sci, South China Sea Inst Oceanol,Ctr Marine Microbiol, CAS Key Lab Trop Marine Bioresources & Ecol, Guangdong Key Lab Marine Mat Med,RNAM, Guangzhou 510301, Guangdong, Peoples R China

[2] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2014年 / 46卷 / 05期

基金：

中国国家自然科学基金;

关键词：

alkyne; 3-aminoazepan-2-one; Michael addition; piperazine-2,5-dione; protecting groups; MYCOBACTERIUM-TUBERCULOSIS; BECKMANN REARRANGEMENT; INHIBITORS; LACTAMS; DERIVATIVES; METATHESIS; ALKALOIDS; CHEMISTRY; DISCOVERY; ANALOGS;

D O I：

10.1055/s-0033-1340473

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and efficient synthesis of novel seven-membered heterocyclic derivatives containing 3-aminoazepan-2-one backbone is described using 1,4-protected piperazine-2,5-diones and alkynes as starting materials. The reaction may undergo Michael addition, unusual nucleophilic attack to an amide group, and keto-enol tautomerization. The reaction showed different reactivity when using substrates with different protecting groups: it had higher efficiency when using either alkanoyl-protecting group with cesium carbonate as the base, or benzoyl-protecting group with triethylamine as the base, but no reaction when using benzyl or allyl protecting groups with a variety of bases (Et3N, DBU, K2CO3, Cs2CO3, KHCO3, CsHCO3, and KOt-Bu).

引用

页码：621 / 628

页数：8

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