35746-43-1Relevant articles and documents
Palladium-catalyzed intramolecular cyclization of ynamides: Synthesis of 4-halo-oxazolones
Huang, Hai,He, Guangke,Zhu, Guohao,Zhu, Xiaolin,Qiu, Shineng,Zhu, Hongjun
, p. 3480 - 3487 (2015)
A mild and efficient methodology involving Pd(PPh3)4-catalyzed intramolecular cyclization of N-alkynyl alkyloxycarbamates with CuCl2 or CuBr2 for the synthesis of 4-halo-oxazolones was developed. This reaction exhibiting good functional tolerance provided a new, efficient, and rapid synthetic process to 4-halo-oxazolones. The resulting 4-halo-oxazolones can serve as great potential precursors for the 3,4,5-trisubstituted oxazolones via a Pd-catalyzed cross-coupling reaction.
An efficient silver tetrafluoroborate-catalyzed cycloisomerization of ynamides
Ieawsuwan, Winai,Ruchirawat, Somsak
, p. 100 - 110 (2019/07/31)
A silver catalyzed-cycloisomerization of N-Boc protected ynamides has been developed under mild reaction conditions to provide a wide range of oxazol-2(3H)-ones in good to excellent yields. Moreover, the acid-promoted Pictet-Spengler cyclization of oxazol
Reaction of Ynamides with Iminoiodinane-Derived Nitrenes: Formation of Oxazolones and Polyfunctionalized Oxazolidinones
Rey-Rodriguez, Romain,Grelier, Gwendal,Habert, Lo?c,Retailleau, Pascal,Darses, Benjamin,Gillaizeau, Isabelle,Dauban, Philippe
, p. 11897 - 11902 (2017/11/24)
This article describes the reaction of ynamides with metallanitrenes generated in the presence of an iodine(III) oxidant. N-(Boc)-Ynamides are converted to oxazolones via a cyclization reaction. The reaction is mediated by a catalytic dirhodium-bound nitrene species that first behaves as a Lewis acid. The oxazolones can be converted in a one pot manner to functionalized oxazolidinones following a regio- and stereoselective oxyamination reaction with the same nitrene reagent generated in stoichiometric amounts.