51269-70-6Relevant academic research and scientific papers
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.
Diastereoselective synthesis of cyclic 1,3-aminoalcohols bearing CF3(CCl3)-groups
Shevchenko, Nikolay E.,R?schenthaler, Gerd-Volker,Mitiaev, Alexander S.,Lork, Enno,Nenajdenko, Valentine G.
scheme or table, p. 637 - 644 (2009/04/03)
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.
New method of preparation of C2F5Li and its reactions with cyclic imines and lactims: Synthesis of α-pentafluoroethyl proline
Shevchenko, Nikolay E.,Nenajdenko, Valentine G.,R?schenthaler, Gerd-Volker
, p. 390 - 396 (2008/12/21)
Addition of pentafluoroethyllithium to cyclic imines leads to pentafluoroethyl substituted pyrrolidines, piperidines and azepanes while reaction of cyclic lactims gives rise to 2-pentafluoroethyl imines. Oxidative cleavage of 2-furyl-2-pentafluoroethyl pyrrolidine has been found to be an effective method for the preparation of a racemic α-pentafluoroethyl proline.
A PRACTICAL PREPARATION OF Δ1-2-SUBSTITUTED AND Δ1-2,3-DISUBSTITUTED PYRROLINES
Haslego, Mark L.,Maryanoff, Cynthia A.,Scott, Lorraine,Sorgi, Kirk L.
, p. 643 - 647 (2007/10/02)
Addition of N-vinylpyrrolidinone and an ester to NaH in THF effects acylation and affords keto lactams (1) in high yields.Hydrolysis of 1 in strong acid generates Δ1-2-substituted pyrrolines (2) in good yield.Keto lactams (1) can be further alkylated and hydrolyzed to produce Δ1-2,3-disubstituted pyrrolines (4) in good isolated yield.
Reaction of Organolithium Reagents with Lactim Ethers: Preparation of Cyclic 2-Alkyl Imines or 2,2-Dialkyl Amines
Zezza, Charles A.,Smith, Michael B.,Ross, Betsy A.,Arhin, Akwasi,Cronin, Patricia L. E.
, p. 4397 - 4399 (2007/10/02)
The reaction of lactim ethers 1-3 with organolithium reagents has been found to be an effective method for the preparation of cyclic 2-alkyl imines 4-6.The method is most effective for the preparation of 2-aryl and sterically hindered 2-alkyl imines.In addition, treatment of 1-3 with excess organolithium provides a facile route to the rare cyclic 2,2-dialkyl amine derivatives 7-9.These reactions are characterized by mild reaction conditions and good yields and constitute a superior route to the title compounds.
