347-37-5Relevant academic research and scientific papers
A simple and efficient method for trifluoroacetylation of arylamines using trifluoroacetic acid and triphosgene
Han, Ki-Jong,Kim, Misoo
experimental part, p. 559 - 561 (2012/06/04)
A simple and efficient one-pot procedure for trifluoroacetylation of arylamines using trifluoroacetic acid and triphosgene is reported. A mixed trifluoroacetic anhydride generated in situ reacts with a variety of arylamines to give the corresponding trifluroacetamides in high yields.
CYCLOPENTANECARBOXAMIDE DERIVATIVES, MEDICAMENTS CONTAINING SUCH COMPOUNDS AND THEIR USE
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Page/Page column 38, (2011/05/06)
The invention relates to cyclopentanecarboxamide derivatives of formula 1, to their use as Fatty Acid Synthase inhibitors, to methods for their therapeutic use and to pharmaceutical compositions containing them, wherein R1, R2, Rsup
Discovery of BI 99179, a potent and selective inhibitor of type i fatty acid synthase with central exposure
Kley, J?rg T.,MacK, Jürgen,Hamilton, Bradford,Scheuerer, Stefan,Redemann, Norbert
scheme or table, p. 5924 - 5927 (2011/10/09)
Based on a high-throughput screen, cyclopentanecarboxanilides were identified as a new chemotype of non-covalent inhibitors of type I fatty acid synthase (FAS). Starting from initial hits we aimed at generating a tool compound suitable for the in vivo validation of FAS as a therapeutic target. Optimisation yielded BI 99179 which is characterised by high potency, remarkably high selectivity and significant exposure (both peripheral and central) upon oral administration in rats.
Copper-catalyzed synthesis of primary arylamines from aryl halides and 2,2,2-trifluoroacetamide
Tao, Chuan-Zhou,Li, Juan,Fu, Yao,Liu, Lei,Guo, Qing-Xiang
, p. 70 - 75 (2008/09/17)
A catalytic method was developed to synthesize primary arylamines from the corresponding aryl bromides and iodides under mild conditions (yields = 80-99%). Crystalline 2,2,2-trifluoroacetamide was used as ammonia surrogate and CuI/N,N′-dimethyl ethylenediamine was used as catalyst to achieve the C-N cross-coupling.
N- and C-attacks on aromatics of phenylnitrenium ion generated from N-phenylhydroxylamine in the presence of trifluoroacetic acid containing polyphosphoric acid or trifluoroacetic anhydride
Takeuchi, Hiroshi,Taniguchi, Tomohito,Ueda, Takahiro
, p. 295 - 300 (2007/10/03)
A phenylnitrenium ion formed from N-phenylhydroxylamine in the presence of trifluoroacetic acid (TFA) containing polyphosphoric acid (PPA) interacts with the counterion -O2CCF3 and the unshared electron-pair of H2O, showing Hammett's ρ values -5.2 and -4.0 for N- and C-attacks on aromatics PhX (X = H, Me, Et, Ph and Cl), respectively. The ratio N-/C-attack for this nitrenium ion is lower than for the nitrenium ion interacting with only the counterion; the latter nitrenium ion is generated by the use of trifluoroacetic anhydride (TFAA) instead of PPA or by reaction of phenyl azide with aromatics in TFA. The ratio for the former nitrenium ion is affected by the aromatic substituent X:X = Me > X = Et > X = Ph > X = H > X = OMe at 20 and 50°C. The order for X = Cl is between those of X = H and X = Ph at 20°C, but highest at 50°C. The ratio is increased by higher reaction temperature and by decreased concentration of TFA. The results are demonstrated from the mechanistic viewpoint for the nitrenium ions.
Mechanisms of the photochemical rearrangement of diphenyl ethers
Haga, Naoki,Takayanagi, Hiroaki
, p. 735 - 745 (2007/10/03)
The mechanism of the photochemical rearrangement of diphenyl ether (1a) was studied. Irradiation of 1a in ethanol gave 2-phenylphenol (2, 42%) and 4-phenylphenol (3, 11%) as rearrangement products, in addition to phenol (4, 30%) and benzene (5, 25%) as diffusion products. Cross-coupling experiments employing [2H10]1a demonstrated that the formation of 2- and 4-phenylphenol was an intramolecular process. Irradiation of 1a in benzene or in toluene gave biphenyls in good yields. The combined yields of rearrangement products (2 and 3) increased with increase of solvent viscosity, with a concomitant decrease in the formation of 4. All the results can be rationalized in terms of excitation of 1a to the singlet state and dissociation to a radical pair intermediate involving phenoxy and phenyl radicals. Intramolecular recombination of these radicals gives rearrangement products, and escape followed by hydrogen abstraction from the solvent gives diffusion products. When position 4 of 1a was occupied by an electron-donating substituent (1b-e), aryloxy-phenyl bond cleavage to give the corresponding rearrangement products prevailed over phenoxy-aryl bond cleavage. The opposite was the case for substrates with an electron-withdrawing substituent at position 4 (1h,i).
Oxygen Sensitization of Electron Capture Response to Isomers of Polycyclic Aromatic Amines and Hydroxides
Campbell, J. A.,Grimsrud, E. P.,Hageman, L. R.
, p. 1335 - 1340 (2007/10/02)
The use of the oxygen-sensitized constant-current electron capture detector (ECD) with gas chromatography for analyte identification is extended by examining the responses of numerous polycyclic aromatic amines and hydroxides where an appropriate EC-enhancing chemical tag has been attached to the amino group or the hydroxy group has been methylated.For the majority of isomeric groups examined, measured response enhancements of the derivatives are sufficiently dependent on structural differences as to provide an additional means by which substitution isomers can be differentiated.The ion chemistry responsible for the EC and oxygen-sensitized responses also has been examined by the use of an atmospheric pressure ionization mass spectrometer (APIMS).
