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 successfully involved in this transformation. Novel trifluoromethylated analogues of nicotine, anabasine, and homoanabasine alkaloids were synthesized.
Shevchenko, Nikolay E.,Vlasov, Katja,Nenajdenko, Valentine G.,R?schenthaler, Gerd-Volker
scheme or table
p. 69 - 74
(2011/02/27)
Diastereoselective synthesis of cyclic 1,3-aminoalcohols bearing CF3(CCl3)-groups
An aldol-type reaction of cyclic imines and cyclic lactims with carbonyl compounds activated by electron withdrawing trifluoromethyl or trichloromethyl groups proceeded without any catalyst under mild condition. β-Hydroxymethyl substituted cyclic imines or imidates are formed as a result of the reaction. The reduction of the prepared imines leads stereoselectively to the cyclic 1,3-aminoalcohols. Application of methyl trifluoropyruvate in this transformation opens an opportunity for the synthesis of γ-aminoacids derivatives which contain pyrrolidine moiety.
Shevchenko, Nikolay E.,R?schenthaler, Gerd-Volker,Mitiaev, Alexander S.,Lork, Enno,Nenajdenko, Valentine G.
scheme or table
p. 637 - 644
(2009/04/03)
Convenient synthesis of melatonin analogues: 2- and 3-substituted -N-acetylindolylalkylamines
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
Nenajdenko, Valentine G.,Zakurdaev, Eugene P.,Prusov, Eugene V.,Balenkova, Elizabeth S.
p. 11719 - 11724
(2007/10/03)
beta-Cycloylpropionitriles; reduction to 2-cyclyl-delta2-pyrrolines and
-
KNOTT
p. 186 - 188
(2007/10/04)
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