Newly intramolecular α-amidoalkylation cyclisation: Use of the N -acyliminium ion with a sulfur atom as a nucleophile
Identifieur interne : 001157 ( France/Analysis ); précédent : 001156; suivant : 001158Newly intramolecular α-amidoalkylation cyclisation: Use of the N -acyliminium ion with a sulfur atom as a nucleophile
Auteurs : Nicolas Hucher [France] ; Adam Dai Ch [France] ; Pierre Netchitai Lo [France] ; Bernard Decroix [France]Source :
- Tetrahedron Letters [ 0040-4039 ] ; 1999.
English descriptors
Abstract
Abstract: Pyrrolidino(or isoindolo)[1, 3]benzothiazines1a, b were efficiently synthesized in a four-step sequence from the knowno-(benzylthio) benzyl alcohol2. The key step was the nucleophilic attack of the sulfur atom ontoN-acyliminium ion6 which was generated in high acidic medium from ω-carbinol lactam5. The last was regioselectively obtained by reduction of the parent imide4.Pyrrolo(or isoindolo)benzothiazines1a and1b were efficiently synthesized in a four-step sequence from alcohol2. The key step was the newly nucleophilic attack of the sulfur atom onto the intermediateN-acyliminium ion.
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DOI: 10.1016/S0040-4039(99)00484-0
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The key step was the nucleophilic attack of the sulfur atom ontoN-acyliminium ion6 which was generated in high acidic medium from ω-carbinol lactam5. The last was regioselectively obtained by reduction of the parent imide4.Pyrrolo(or isoindolo)benzothiazines1a and1b were efficiently synthesized in a four-step sequence from alcohol2. 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