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

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...

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Published inSynthesis (Stuttgart) Vol. 46; no. 5; pp. 621 - 628
Main Authors Liao, Shengrong, Qin, Chun, Yao, Peifen, Li, Jinsheng, Zhou, Xuefeng, Wang, Junfeng, Huang, Zhishu, Liu, Yonghong
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 02.01.2014
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Michael addition
MYCOBACTERIUM-TUBERCULOSIS
piperazine-2,5-dione
ANALOGS
DISCOVERY
3-aminoazepan-2-one
protecting groups
CHEMISTRY
alkyne
LACTAMS
INHIBITORS
DERIVATIVES
METATHESIS
BECKMANN REARRANGEMENT
ALKALOIDS
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Summary: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).
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0033-1340473