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Synthesis 2014; 46(05): 621-628
DOI: 10.1055/s-0033-1340473
paper
© Georg Thieme Verlag Stuttgart · New York

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

Shengrong Liao
a   CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Materia Medica/RNAM, Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301, P. R. of China   Fax: +86(20)89023244   eMail: yonghongliu@scsio.ac.cn
,
Chun Qin
a   CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Materia Medica/RNAM, Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301, P. R. of China   Fax: +86(20)89023244   eMail: yonghongliu@scsio.ac.cn
,
Peifen Yao
b   School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou, 510006, P. R. of China
,
Jinsheng Li
a   CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Materia Medica/RNAM, Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301, P. R. of China   Fax: +86(20)89023244   eMail: yonghongliu@scsio.ac.cn
,
Xuefeng Zhou
a   CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Materia Medica/RNAM, Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301, P. R. of China   Fax: +86(20)89023244   eMail: yonghongliu@scsio.ac.cn
,
Junfeng Wang
a   CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Materia Medica/RNAM, Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301, P. R. of China   Fax: +86(20)89023244   eMail: yonghongliu@scsio.ac.cn
,
Zhishu Huang
b   School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou, 510006, P. R. of China
,
Yonghong Liu*
a   CAS Key Laboratory of Tropical Marine Bio-resources and Ecology/Guangdong Key Laboratory of Marine Materia Medica/RNAM, Center for Marine Microbiology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301, P. R. of China   Fax: +86(20)89023244   eMail: yonghongliu@scsio.ac.cn
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Publikationsverlauf

Received: 06. Oktober 2013

Accepted after revision: 25. November 2013

Publikationsdatum:
02. Januar 2014 (online)

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Abstract

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).

Key words

alkyne - 3-aminoazepan-2-one - Michael addition - piperazine-2,5-dione - protecting groups

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    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
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