951010-00-7Relevant academic research and scientific papers
Synthesis of Exo- and Endocyclic Enamides Through Copper-Catalyzed Regioselective Intramolecular N-Halovinylation
Bergeron, Jodrey,Daoust, Benoit,Gilbert, Nicolas,Lambolez, Pierre,Ricard, Simon
, (2020/05/04)
Cross-couplings between amides and 1,2-dihaloalkenes are an efficient and straightforward way to access β-haloenamides which, in turn, can be functionalized into complex, stereodefined enamide motifs. However, the intramolecular version of these cross-couplings, leading to cyclic β-haloenamides, has not been formally studied. In this paper, we report an investigation of factors affecting the efficiency of the reaction and its selectivity between potential exo and endo cyclization products. We demonstrate that exo/endo selectivity is largely determined by ring strain, whether it arises from the size of the resulting ring or from the structure of the starting compound, but that selectivity can also be modulated by varying reaction conditions. Finally, we show that resulting β-haloenamides readily undergo transition metal-catalyzed reactions, making this sequence a viable way to access highly functionalized cyclic enamides.
Comparison between Conventional and Nonconventional Methods for the Synthesis of Some 2-Oxazolidinone Derivatives and Preliminary Investigation of Their Inhibitory Activity Against Certain Protein Kinases
Ziane,Mazari,Safer,Sad El Hachemi Amar,Ruchaud,Baratte,Bach
, p. 1061 - 1069 (2019/09/06)
A series of propargyl and allyl carbamates were prepared directly from propargyl and allyl alcohols and phenyl or cyclohexyl isocyanate or indirectly by generating the isocyanates in situ from the corresponding Cbz-protected amines. The obtained carbamate
Gold-catalyzed cyclization of O-propargyl carbamates under mild conditions: A convenient access to 4-alkylidene-2-oxazolidinones
Ritter, Stefanie,Horino, Yoshikazu,Lex, Johann,Schmalz, Hans-Günther
, p. 3309 - 3313 (2008/09/18)
On treatment with catalytic amounts of gold(I) chloride (AuCl) and a base co-catalyst, O-propargyl carbamates smoothly undergo a 5-exo-dig cyclization at room temperature to afford 4-methylene-2-oxazolidinones in high yield. Substrates with a substituent
