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Synthesis 2014; 46(05): 621-628
DOI: 10.1055/s-0033-1340473
DOI: 10.1055/s-0033-1340473
paper
One-Pot Synthesis of Polysubstituted 3-Amino-2-oxo-2,7-dihydro-1H-azepines
Weitere Informationen
Publikationsverlauf
Received: 06. Oktober 2013
Accepted after revision: 25. November 2013
Publikationsdatum:
02. Januar 2014 (online)
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 groupsSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
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