170165-89-6Relevant academic research and scientific papers
A new route to 2-oxazolines, bis-oxazolines, and 2-Imidazoline-5-ones from imidates using solvent-free cycloadditions: Synthesis, chemical properties, and PM3 MO calculations
Lerestif, Jean Michel,Toupet, Loic,Sinbandhit, Sourisak,Tonnard, Francois,Bazureau, Jean Pierre,Hamelin, Jack
, p. 6351 - 6364 (1997)
The 1,3-dipolar cycloadditions between imidate 1, derived from dimethylaminomalonate and aldehydes 2(a-f), phthalaldehyde 2g, isophthalaldehyde 2h. 4-chlorophenylisocyanate 9a, ethoxycarbonylisothiocyanate 9d as dipolarophiles proceeds regioselectively in
Lewis acid catalyzed dipolar cycloadditions of an activated imidate
Bowman, Roy K.,Johnson, Jeffrey S.
, p. 8537 - 8540 (2007/10/03)
An evaluation of simple Lewis acids revealed that N-malonylimidates undergo catalyzed [3+2] cycloaddition reactions with aldehydes, imines, and activated olefins to form oxazolines, imidazolines, and pyrrolines, respectively. Reactions proceed optimally at ambient temperature with the addition of 5 mol % of MgCl2 in CH3CN. Experiments aimed at elucidation of the reactive intermediate undergoing cycloaddition suggest that the Lewis acid promotes a 1,2-prototropic shift to give a metal-coordinated azomethine ylide, rather than ionization and proton transfer to give a nitrile ylide.
