119866-82-9Relevant academic research and scientific papers
Methyl 3,3,3-trifluoropyruvate hemiaminals: Stability and transaminations
Dolensky, Bohumil,Kví?ala, Jaroslav,Paleta, Old?ich
, p. 745 - 751 (2005)
Hemiaminals of methyl 3,3,3-trifluoropyruvate with aromatic amines, benzylic monoamines and diamines were prepared and their interconversions studied using NMR spectrometry. In solution, benzylic hemiaminals were found to be stable in contrast to aromatic hemiaminals, which, in turn, were stable in the solid state.
New nucleophilic rearrangement in the mechanism of the three-component domino cyclisation affording fluoroalkylated (pyrrolo)quinazolines
Paleta, Old?ich,Dolensky, Bohumil,Pale?ek, Ji?í,Kví?ala, Jaroslav
, p. 1 - 11 (2014/01/06)
The following mechanism steps were verified for the three-component domino cyclisation affording (pyrrolo)quinazolines from 2-(aminomethyl)aniline, a very reactive oxo compound and "usual" oxo compound. The first step was a rapid reaction of very reactive oxo compound (trifluoropyruvate or hexafluoroacetone) with benzylic amino group to form hemiaminal, but not imine; the second step was the reaction of oxo compound with aromatic amino group to form imine (Schiff base) being in equilibrium with its enamine form; the third step was an intramolecular attack of the hemiaminal carbon by the enamine carbon followed by a new nucleophilic rearrangement to form tetrahydropyrimidine cycle; the forth step was closure of the lactam ring, if ester group was available as in trifluoropyruvate.2013 Elsevier B.V. All rights reserved.
Preparation of new trifluoromethyl substituted Tri- and tetracyclic heterocycles with peganin skeleton from a methyl 3,3,3-trifluoropyruvate/2-aminobenzylamine adduct
Dolensky, Bohumil,Kvicala, Jaroslav,Paleta, Oldrich,Cejka, Jan,Ondracek, Jan
, p. 6939 - 6942 (2007/10/03)
Addition of 2-aminobenzylamino to methyl trifluoropyruvate afforded methyl 2-((2-aminobenzyl)amino)-3,3,3-trifluoro-2-hydroxypropionate, which reacted with various ketones to give new fluorinated tricyclic and tetracyclic heterocycles with the skeleton of
FLUORINE-CONTAINING AMINO ACIDS. V. IMINES OF TRIFLUOROPYRUVIC ACID IN THE SYNTHESIS OF N-SUBSTITUTED TRIFLUOROALANINES
Soloshonok, V. A.,Yagupol'skii, Yu. L.,Kukhar, V. P.
, p. 1478 - 1482 (2007/10/02)
N-Substituted trifluoroalanine methyl esters were obtained by the reduction of the corresponding imines of trifluoropyruvic acid with zinc in acetic acid.The N-butyl- and N-(1-phenylethyl)imines undergo a -proton shift under the influence of bases with the formation of trifluoroalanine derivatives.It was found that the N-(1-phenylethyl)imine of tetrafluoropyruvic acid is formed directly from the corresponding amine and methyl trifluoropyruvate under conditions with azeotropic distillation of the water with toluene in the presence of acidic catalysis.
