Journal
SYNTHESIS-STUTTGART
Volume 46, Issue 5, Pages 621-628Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0033-1340473
Keywords
alkyne; 3-aminoazepan-2-one; Michael addition; piperazine-2,5-dione; protecting groups
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Funding
- 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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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).
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