The reaction of cyclic imines with the Ruppert–Prakash reagent. Facile approach to α-trifluoromethylated nornicotine, anabazine, and homoanabazine

We have demonstrated that the Ruppert–Prakash reagent is able to react with a number of cyclic imines under acidic condition to afford the corresponding α-trifluoromethyl derivatives of nitrogen heterocycles. 5–7-Membered cyclic imines bearing various alkyl, aryl or heterocyclic group were successfu...

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Bibliographic Details
Published in:Tetrahedron 2011-01, Vol.67 (1), p.69-74
Main Authors: Shevchenko, Nikolay E., Vlasov, Katja, Nenajdenko, Valentine G., Röschenthaler, Gerd-Volker
Format: Article
Language:English
Subjects:
Alkaloids
anabasine
Aromatic compounds
Bearing
chemical reactions
Cyclic imines
Derivatives
Imines
Nicotine
nitrogen
nornicotine
Nucleophilic trifluoromethylation
Ruppert–Prakash reagent
synthesis
Tetrahedrons
Transformations
α-trifluoromethylated alkaloids
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Summary:We have demonstrated that the Ruppert–Prakash reagent is able to react with a number of cyclic imines under acidic condition to afford the corresponding α-trifluoromethyl derivatives of nitrogen heterocycles. 5–7-Membered cyclic imines bearing various alkyl, aryl or heterocyclic group were successfully involved in this transformation. Novel trifluoromethylated analogues of nicotine, anabasine, and homoanabasine alkaloids were synthesized. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.11.032