104704-31-6Relevant articles and documents
The reaction of cyclic imines with the Ruppert-Prakash reagent. Facile approach to α-trifluoromethylated nornicotine, anabazine, and homoanabazine
Shevchenko, Nikolay E.,Vlasov, Katja,Nenajdenko, Valentine G.,R?schenthaler, Gerd-Volker
scheme or table, p. 69 - 74 (2011/02/27)
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.
Convenient synthesis of melatonin analogues: 2- and 3-substituted -N-acetylindolylalkylamines
Nenajdenko, Valentine G.,Zakurdaev, Eugene P.,Prusov, Eugene V.,Balenkova, Elizabeth S.
, p. 11719 - 11724 (2007/10/03)
A new method for the synthesis of 2- and 3-substituted indolylalkylamides, derivatives of melatonin, from arylhydrazines and amidoketones by the Fischer reaction was elaborated. The amidoketones can be easily prepared from cyclic imines by reaction with acylpyridinium chloride. This method is a one-step synchronous creation of the selected alkylamide fragment and the indole core. Variation of the arylhydrazines create the desired substituents in the carbocycle of indolylalkylamides and suitable choice of amidoketone can direct the amidoalkyl chain to the 2- or 3-position of the indole. Graphical Abstract
