664342-20-5Relevant academic research and scientific papers
Practical synthesis of ethyl 3-fluoro-1-pyrrole-2-carboxylate: A key fragment of a potent drug candidate against hepatitis b virus
René, Adeline,Quilan, Maxime,Deng, Yicheng,Cheng, Yang,Teleha, Christopher A.,Raboisson, Pierre,Bonfanti, Jean-Fran?ois,Fortin, Jér?me,Charette, André. B.,Pannecoucke, Xavier,Poisson, Thomas,Jubault, Philippe
, p. 792 - 801 (2019/10/16)
We report herein the development of two efficient synthetic routes for the preparation of a key fragment required for the synthesis of potent drug candidates of Hepatitis B virus. The ethyl 3-fluoro-1-H-pyrrole-2-carboxylate scaffold was synthesized from readily available starting materials in good overall yields. The scalability of one of the developed routes was demonstrated and afforded the desired target in good yield and excellent purity (99%).
Ring-closing metathesis of vinyl fluorides towards α-fluorinated α,β-unsaturated lactams and lactones
Marhold, Michael,Stillig, Christian,Fr?hlich, Roland,Haufe, Günter
supporting information, p. 5777 - 5785 (2014/10/15)
Ring-closing olefin metathesis reactions (RCM) using Grubbs II or Hoveyda's catalysts have been applied to a series of N-alkenyl-N-benzyl-α-fluoroacrylamides. α-Fluoro-α,β-unsaturated γ- or δ-lactams incorporating a fluorinated double bond were obtained in moderate to good yields, depending on the nature of substituents on the benzyl ring. The corresponding seven- and eight-membered lactams were not formed under similar conditions. When the N-benzyl group was replaced by an N-tosyl group, the corresponding ε-lactam was also formed in 38% yield. When N-(2-fluoroallyl) derivatives were used instead of fluoroacryloyl derivatives, six-, seven-, and eight-membered N-heterocycles were obtained in low yields. This method was also used to synthesize fluorinated α,β-unsaturated analogues of pyrrolizidine and indolizidine alkaloids from prolinol, and also to synthesize N-benzyl-3-fluoroquinolone in three steps from commercially available 2-vinylaniline in 44% overall yield. Also 3-fluorocoumarin and 3-fluorochromene were prepared from ovinylphenol, and 3-fluoro-benzoxepine was available from o-allylphenol.
A ring-closing metathesis pathway to fluorovinyl-containing nitrogen heterocyles
De Matteis, Valeria,Van Delft, Floris L.,Tiebes, Joerg,Rutjes, Floris P. J. T.
, p. 1166 - 1176 (2007/10/03)
The synthesis of highly functionalized fluorinated piperidines is described. The key step in this synthesis is a ring-closing metathesis reaction involving fluoride-substituted olefins, which leads to the corresponding cyclic vinyl fluorides. Several sequences to arrive at differently substituted piperidines have been evaluated. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Synthesis of vinyl fluorides by ring-closing metathesis
Marhold, Michael,Buer, Anna,Hiemstra, Henk,Van Maarseveen, Jan H.,Haufe, Günter
, p. 57 - 60 (2007/10/03)
The first ring-closing olefin metatheses of alkenyl α- fluoroacrylamides or acrylates incorporating a fluorinated double bond are reported. Several N-benzyl-N-alkenyl-α-fluoroacrylamides were cyclized in the presence of 2mol% of Grubbs II catalyst at room
