One-Pot Synthesis of Polysubstituted 3-Amino-2-oxo-2,7-dihydro-1H-azepines
Liao, SR; Qin, C; Yao, PF; Li, JS; Zhou, XF; Wang, JF; Huang, ZS; Liu, YH; yonghongliu@scsio.ac.cn
2014
发表期刊SYNTHESIS-STUTTGART
ISSN0039-7881
卷号46期号:5页码:621-628
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).
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
关键词Alkyne 3-aminoazepan-2-one Michael Addition Protecting Groups Piperazine-2 5-dione
学科领域Chemistry
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] ; 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] ; 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] ; 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]
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收录类别sci
资助项目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] ; 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] ; 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] ; 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]
WOS记录号WOS:000336838400007
引用统计
被引频次:1[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.scsio.ac.cn/handle/344004/10461
专题中科院海洋生物资源可持续利用重点实验室
通讯作者yonghongliu@scsio.ac.cn
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GB/T 7714
Liao, SR,Qin, C,Yao, PF,et al. One-Pot Synthesis of Polysubstituted 3-Amino-2-oxo-2,7-dihydro-1H-azepines[J]. SYNTHESIS-STUTTGART,2014,46(5):621-628.
APA Liao, SR.,Qin, C.,Yao, PF.,Li, JS.,Zhou, XF.,...&yonghongliu@scsio.ac.cn.(2014).One-Pot Synthesis of Polysubstituted 3-Amino-2-oxo-2,7-dihydro-1H-azepines.SYNTHESIS-STUTTGART,46(5),621-628.
MLA Liao, SR,et al."One-Pot Synthesis of Polysubstituted 3-Amino-2-oxo-2,7-dihydro-1H-azepines".SYNTHESIS-STUTTGART 46.5(2014):621-628.
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