114564-88-4Relevant academic research and scientific papers
Silver-Catalyzed Cyclization of Propargylic Amides to Oxazolines
Wong, Valerie H. L.,White, Andrew J. P.,Hor,Hii
supporting information, p. 3943 - 3948 (2016/01/25)
A ligand-accelerated effect is observed in the cyclization of propargylic amides catalyzed by bis(pyridyl)silver(I) complexes, with an unexpected reversal of electronic demand to the analogous NH addition reaction. The catalyst was found to be effective for internal alkyne substrates, offering exclusive selectivity for the 5-exo-dig product. Differences in selectivity profile between gold- and silver-catalyzed processes are highlighted and discussed.
Synthesis of substituted oxazoles from N-benzyl propargyl amines and acid chlorides
Wachenfeldt, Henrik V.,Paulsen, Filip,Sundin, Anders,Strand, Daniel
, p. 4578 - 4585 (2013/07/26)
The reaction between N-benzylpropargylamines and acid chlorides at elevated temperatures provides efficient, direct access to a variety of di- and tri-substituted oxazoles. The versatility of this reaction is explored and 21 examples are demonstrated. The usefulness of the methodology is showcased through the short and efficient formal syntheses of medicinally relevant drugs aleglitazar and romazarit. The reaction between N-benzylpropargylamines and acid chlorides at elevated temperatures gives oxazoles in up to 99 % yield. Twenty-one examples are demonstrated varying the substitution at all positions of the heterocycle. Copyright
