1375415-53-4Relevant academic research and scientific papers
Chemo- and stereoselective synthesis of fluorinated enamides from ynamides in HF/pyridine: Second-generation approach to potent ureas bioisosteres
Métayer, Beno?t,Compain, Guillaume,Jouvin, Kévin,Martin-Mingot, Agnès,Bachmann, Christian,Marrot, Jér?me,Evano, Gwilherm,Thibaudeau, Sébastien
, p. 3397 - 3410 (2015)
(E)- and (Z)-α-fluoroenamides could be easily prepared with high levels of chemo- and regioselectivities by hydrofluorination of readily available ynamides with HF/pyridine. The scope and limitations of this new process for the hydrofluorination of ynamides, as well as the stability of the resulting α-fluoroenamides, have been extensively studied. Theoretical calculations at the MP2 and B3LYP levels of theory showed that the resulting fluoroenamides exhibit geometrical and electronic properties that partially mirror those of ureas, therefore demonstrating that the hydrofluorination of ynamides provides a general, straightforward, and user-friendly approach to bioisosteres of ureas, potent building blocks for biological studies and medicinal chemistry.
Stereoselective hydrofluorination of ynamides: A straightforward synthesis of novel α-fluoroenamides
Compain, Guillaume,Jouvin, Kevin,Martin-Mingot, Agnes,Evano, Gwilherm,Marrot, Jerome,Thibaudeau, Sebastien
supporting information; experimental part, p. 5196 - 5198 (2012/06/01)
α-Fluoroenamides, potent rigid fluorinated bioisosters of ureas, have been synthesized by a highly regio- and stereo-selective hydrofluorination of ynamides in anhydrous HF. This reaction provides the first general entry to α-fluoroenamides and can easily be applied to a wide range of substrates.
