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Newly intramolecular α-amidoalkylation cyclisation: Use of theN-acyliminium ion with a sulfur atom as a nucleophile

✍ Scribed by Nicolas Hucher; Adam Dai¨ch; Pierre Netchitai¨lo; Bernard Decroix

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 215 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)00484-0

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✦ Synopsis

Pyrrolidino(or isoindolo) [ 1,3]benzothiazines I a,b were efficiently synthesized in a four-step sequence from the known o-(benzylthio) benzyl alcohol 2. The key step was the nucleophilic attack of the sulfur atom onto N-acyliminium ion 6 which was generated in high acidic medium from 6o-carbinol lactam 5. The last was regioselectively obtained by reduction of the parent imide 4.

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✍ Nicolas Hucher; Adam Daich; Pierre Netchitailo; Bernard Decroix 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 32 KB 👁 1 views