1228672-40-9Relevant 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 (2015/04/22)
(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.
Regio- and stereospecific synthesis of (E)-α-iodoenamide moieties from ynamides through iodotrimethylsilane-mediated hydroiodation
Sato, Akihiro H.,Ohashi, Kazuhiro,Iwasawa, Tetsuo
, p. 1309 - 1311 (2013/03/13)
A facile approach to (E)-α-haloenamide moieties from ynamides using bromo- or iodotrimethylsilane is described. The simple protocol enables a regio- and stereospecific hydrohalogenation of the triple bond in gram-scale and provides a general entry for synthesis of novel enamide analogues.
Copper-mediated selective cross-coupling of 1,1-dibromo-1-alkenes and heteronucleophiles: Development of general routes to heterosubstituted alkynes and alkenes
Jouvin, Kevin,Coste, Alexis,Bayle, Alexandre,Legrand, Frederic,Karthikeyan, Ganesan,Tadiparthi, Krishnaji,Evano, Gwilherm
, p. 7933 - 7947 (2013/01/16)
Efficient and general procedures for the cross-coupling of 1,1-dibromoalkenes and N-, O-, and P-nucleophiles are reported. Fine-tuning of the reaction conditions allows for either site-selective, double, or alkynylative cross-coupling, therefore providing
Copper-free sonogashira cross-coupling of ynamides: Easy access to various substituted ynamides from nonsubstituted ynamides
Wakamatsu, Hideaki,Takeshita, Mitsuhiro
experimental part, p. 2322 - 2324 (2010/11/03)
It is demonstrated herein that palladium-catalyzed Sonogashira cross-coupling of ynamides can be accomplished with moderate to good yields of substituted ynamides in the absence of copper salt, and NaOAc plays an important role in this reaction as an addi
