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学科主题: Chemistry
题名: One-Pot Synthesis of Polysubstituted 3-Amino-2-oxo-2,7-dihydro-1H-azepines
作者: Liao, SR ; Qin, C ; Yao, PF ; Li, JS ; Zhou, XF ; Wang, JF ; Huang, ZS ; Liu, YH
通讯作者: yonghongliu@scsio.ac.cn
关键词: alkyne ; 3-aminoazepan-2-one ; Michael addition ; piperazine-2,5-dione ; protecting groups
刊名: SYNTHESIS-STUTTGART
发表日期: 2014
卷: 46, 期:5, 页:621-628
收录类别: sci
部门归属: [Liao, Shengrong ; Qin, Chun ; Li, Jinsheng ; Zhou, Xuefeng ; Wang, Junfeng ; Liu, Yonghong] 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 ; [Yao, Peifen ; Huang, Zhishu] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China
项目归属: LMB
资助者: National Key Basic Research Program of China (973)'s Project [2010CB833800, 2011CB915503]; National High Technology Research and Development Program (863 Program) [2012AA092104]; National Natural Science Foundation of China [31270402, 21172230, 30973679, 41176148, 21002110]; Guangdong Province-CAS Joint Research Program [2011B090300023, 2012B091100264]; Guangdong Marine Economic Development and Innovation of Regional Demonstration Project [GD2012-D01-001, GD2012-D01-002]
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).
原文出处: 查看原文
WOS记录号: WOS:000336838400007
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内容类型: 期刊论文
URI标识: http://ir.scsio.ac.cn/handle/344004/10461
Appears in Collections:中科院海洋生物资源可持续利用重点实验室_期刊论文

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Recommended Citation:
Liao, SR; Qin, C; Yao, PF; Li, JS; Zhou, XF; Wang, JF; Huang, ZS; Liu, YH.One-Pot Synthesis of Polysubstituted 3-Amino-2-oxo-2,7-dihydro-1H-azepines,SYNTHESIS-STUTTGART,2014,46(5):621-628
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