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

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 a...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2014-01, Vol.46 (5), p.621-628
Main Authors: Liao, Shengrong, Qin, Chun, Yao, Peifen, Li, Jinsheng, Zhou, Xuefeng, Wang, Junfeng, Huang, Zhishu, Liu, Yonghong
Format: Article
Language:English
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Summary: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 (Et 3 N, DBU, K 2 CO 3 , Cs 2 CO 3 , KHCO 3 , CsHCO 3 , and KO t -Bu).
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0033-1340473