✦ LIBER ✦
Unexpected reversible nitrogen atom transfer in the synthesis of polysubstituted imides and 7-aza-hexahydroindolones via enaminonitrile γ-lactams
✍ Scribed by Nabila Oukli; Sébastien Comesse; Nafa Chafi; Hassan Oulyadi; Adam Daïch
- Book ID
- 104096205
- Publisher
- Elsevier Science
- Year
- 2009
- Tongue
- French
- Weight
- 531 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
An effective route to novel polysubstituted imides is described, which involves the reaction of enaminonitrile c-lactams derived from N-alkylated a-bromoacetamides and malononitrile with acryloyl chloride derivatives. This preceded via a sequence 1,4-addition-intramolecular peptidic coupling and a c-lactam hydrolysis in a one 'pot-procedure'. These imides were regioselectively reduced into corresponding Nacyliminium precursors, which subsequently submitted to an intramolecular aza-cyclization in acidic medium to provide novel 7-hexahydro-aza-indoles.