106942-38-5Relevant academic research and scientific papers
Dakin-west reaction of n-thioacylprolines using trifluoroacetic anhydride: Novel access to 5-trifluoromethylthiazoles
Hagimoto, Yuri,Saijo, Ryosuke,Kawase, Masami
, p. 709 - 724 (2014/04/03)
The reaction between N-thioacylprolines and trifluoroacetic anhydride in the presence of pyridine afforded a good yield of 5-trifluoromethylthiazoles. This reaction proceeded through mesoionic 1,3-thiazolium-5-olates, followed by cleavage of the pyrrolidine ring and the formation of thiazoles, introducing a trifluoromethyl group at position 5 in the thiazole ring.
Synthesis of peptidyl fluoromethyl ketones and peptidyl α-keto esters as inhibitors of porcine pancreatic elastase, human neutrophil elastase, and rat and human neutrophil cathepsin G
Peet,Burkhart,Angelastro,Giroux,Mehdi,Bey,Kolb,Neises,Schirlin
, p. 394 - 407 (2007/10/02)
Comparison of MeO-Suc-Val-Pro-Phe-CO2Me (29) and MeO-Suc-Ala-Ala-Pro-Phe-CO2Me (25) with their corresponding trifluoromethyl ketones 9a and 9b, respectively, in rat and human neutrophil cathepsin G assays showed the α-keto esters to
Synthesis of Fluorinated α-Amino Ketones, III. Preparation of Fluorinated Ketone Analogues of Phenylalanine, Lysine, and p-(Guanidino)phenylalanine
Kolb, Michael,Neises, Bernhard,Gerhart, Fritz
, p. 1 - 6 (2007/10/02)
The synthesis of α-amino mono-, di-, and trifluoromethyl and difluoromethylene ketones and their derivatives is described.A one-pot sequence related to the Dakin-West reaction starts from amino acids and gives the corresponding fluorinated ketone analogue
SYNTHESIS OF FLUORINATED α-AMINO KETONES PART I: α-BENZAMIDOALKYL MONO- DI- AND TRIFLUOROMETHYL KETONES
Kolb, Michael,Barth, Jacqueline,Neises, Bernhard
, p. 1579 - 1582 (2007/10/02)
2-Phenyl-5(4H)-oxazolones, obtained from α-amino acids, are reacted with di- and trifluoro acetic anhydride by a modified Dakin-West procedure to yield in a one-pot reaction α-benzamidoalkyl-di- and trifluoromethyl ketones in good yields.The monofluoromethyl analogues were also prepared from α-amino acids, however the use of the highly toxic fluoroacetic anhydride was avoided.The key step is the halogen exchange reaction on the corresponding bromomethyl ketone.
