808737-53-3Relevant academic research and scientific papers
Silver-catalyzed preparation of oxazolines from N-propargylamides
Harmata, Michael,Huang, Chaofeng
experimental part, p. 1399 - 1401 (2009/04/06)
Treatment of N-propargylamides with 5 mol% of silver hexafluoroantimonate results in the rapid formation of oxazolines in essentially quantitative yield. Georg Thieme Verlag Stuttgart.
Gold catalysis: Mild conditions for the synthesis of oxazoles from N-propargylcarboxamides and mechanistic aspects
Hashmi, A. Stephen K.,Weyrauch, Jan P.,Frey, Wolfgang,Bats, Jan W.
, p. 4391 - 4394 (2007/10/03)
(Chemical Equation Presented) 2,5-Disubstituted oxazoles are synthesized from the corresponding propargylcarboxamides under mild reaction conditions via homogeneous catalysis by AuCl3. While monitoring the conversion via 1H NMR spectroscopy, an intermediate 5-methylene-4,5-dihydrooxazole can be observed and accumulated up to 95%, being the first direct and catalytic preparative access to such alkylidene oxazolines. The intermediate was fully characterized and can be trapped at -25°C for several weeks. Deuteration experiments show a stereospecific mode of the two first steps of the reaction.
