126402-01-5Relevant academic research and scientific papers
Three-component (Domino) reaction affording substituted pyrroloquinazolines: Cyclization regioselectivity and stereoselectivity
Paleta, Oldrich,Dolensky, Bohumil,Palecek, Jiri,Kvicala, Jaroslav
, p. 1262 - 1270 (2013)
The cyclization involving 2-(aminomethyl)aniline, methyl 3,3,3-trifluoropyruvate, and various oxo compound afforded linearly annulated pyrroloquinazolines, for example, (2R,3aS)-2-hydroxy-3a-phenyl-2- trifluoromethyl-3,3a,4,9-tetrahydropyrrolo[2,1-b]quina
A convenient synthesis of 4-trifluoromethyl-(2H)-pyridazin-3-ones from methyl 3,3,3-trifluoropyruvate
Sibgatulin, Dmitriy A.,Volochnyuk, Dmitriy M.,Kostyuk, Alexandr N.
, p. 1907 - 1911 (2005)
A convenient two-step synthesis of 4-CF3-(2H)-pyridazin-3-ones starting from methyl 3,3,3-trifluoropyruvate (MeTFP) and carbonyl compounds has been elaborated. As a result, a set of various 4-CF3-(2H)-pyridazin- 3-ones was obtained.
Novel and convenient aldolization of methyl 3,3,3-trifluoropyruvate using enamines instead of ketones
Palecek, Jiri,Paleta, Oldrich
, p. 521 - 524 (2004)
Piperidine enamines derived from acetone, acetophenone, cyclopentanone and cyclohexanone react easily in minutes with methyl 3,3,3-trifluoropyruvate (1) to afford products of the aldol condensation in high yields at room temperature, which is in contrast to the direct aldolization of 1 with the ketones.
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.
Fluorinated butanolides and butenolides: Part 8. 2-(Trifluoromethyl)butan-4-olides by synthesis from methyl 3,3,3-trifluoropyruvate as building block
Paleta, Old?ich,Pale?ek, Ji?í,Dolensky, Bohumil
, p. 175 - 184 (2007/10/03)
2-Hydroxy-2-trifluoromethylbutan-4-olides (8-10) were prepared by a four step synthesis starting from a ketone and methyl 3,3,3-trifluoropyruvate (1) as a building block. Uncatalyzed chemospecific aldolization of ketones with 1 afforded 2 hydroxy-4-oxoest
