2549-31-7Relevant articles and documents
NOVEL DEHYDROGENATION OF 2,5-DIARYLSUBSTITUTED Δ2-OXAZOLINES TO OXAZOLES
Klein, Robert F. X.,Horak, Vaclav,Baker, Godfrey A. S.
, p. 1631 - 1635 (1993)
The dehydrogenation of various 2,5-diaryl substituted Δ2-oxazolines with either Br2/LiBr/CaCO3 (molar ratio 1.05 : 2 : 3) or CuBr2/LiBrCaCO3 (2 : 1 :3) in refluxing o-dichlorobenzene gives the corresponding oxazole in up to 87percent yield.Free radical benzylic bromination followed by dehydrobromination is the expected dehydrogenation mechanism.The successful application of the reagent combination for this transformation is in contrast to standard dehydrogenation reagents, including N-bromosuccinimide, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, chloranil, NiO2 and active γ-MnO2.
Alkynyl Thioethers in Gold-Catalyzed Annulations To Form Oxazoles
Reddy, Raju Jannapu,Ball-Jones, Matthew P.,Davies, Paul W.
supporting information, p. 13310 - 13313 (2017/10/07)
Non-oxidative, regioselective, and convergent access to densely functionalized oxazoles is realized in a functional-group tolerant manner using alkynyl thioethers. Sulfur-terminated alkynes provide access to reactivity previously requiring strong donor-substituted alkynes such as ynamides. Sulfur does not act in an analogous donor fashion in this gold-catalyzed reaction, thus leading to complementary regioselective outcomes and addressing the limitations of using ynamides.
One-pot preparation of 2,5-disubstituted and 2,4,5-trisubstituted oxazoles from aromatic ketones with molecular iodine, oxone, and trifluoromethanesulfonic acid in nitriles
Imai, Sho,Kikui, Hiroki,Moriyama, Katsuhiko,Togo, Hideo
, p. 5267 - 5274 (2015/07/15)
Alkyl aryl ketones were successfully converted into the corresponding 2,5-disubstituted and 2,4,5-trisubstituted oxazoles in good to moderate yields in a one-pot manner, utilizing iodine, Oxone, and trifluoromethanesulfonic acid in nitriles under transition-metal-free conditions. The present method could be used for the preparation of Oxaprozin from benzyl phenyl ketone and succinonitrile. A possible reaction mechanism was proposed in which the key intermediates were α-iodoalkyl aryl ketones and α-iodosylalkyl aryl ketones.