855841-59-7Relevant academic research and scientific papers
Iodine(III)-Catalyzed Formal [2 + 2 + 1] Cycloaddition Reaction for Metal-Free Construction of Oxazoles
Yagyu, Takuma,Takemoto, Yusuke,Yoshimura, Akira,Zhdankin, Viktor V.,Saito, Akio
supporting information, p. 2506 - 2509 (2017/05/24)
The iodine(III) catalyst, in situ generated from iodoarene as a precatalyst with m-CPBA and Tf2NH, promoted the metal-free [2 + 2 + 1] cycloaddition-type reactions of alkynes, nitriles, and oxygen atoms for the regioselective formations of 2,4-disubstituted and 2,4,5-trisubstituted oxazole. A first example of iodine catalysis for multicomponent reactions is represented.
Metal-free syntheses of oxazoles and their analogues based on λ3-iodane-mediated cycloisomerization/functionalization reactions or [2+2+1] cycloaddition type reactions
Saito, Akio
, p. 84 - 98 (2017/04/17)
As a metal-free construction of oxazoles and furans concomitant with the introduction of oxygen functional groups or fluorine atoms into the side chains, we have developed λ3-iodane-mediated cycloisomerization/functionalization reactions of propargyl compounds. In these reactions, aryl- λ3-iodane ArI(X)Y works not only as a donor of heteroatomic functional groups but also as an activator of carbon-carbon triple bonds. Therefore, this methodology is not required any transition metal catalysts, which are frequently used in previous methods. Furthermore, this methodology can be extended to λ3-iodane-mediated [2+2+1] cycloaddition type reactions of alkynes, nitriles and heteroatoms for metal-free formation of oxazoles and imidazoles.
Metal-free [2 + 2 + 1] annulation of alkynes, nitriles, and oxygen atoms: Iodine(III)-mediated synthesis of highly substituted oxazoles
Saito, Akio,Taniguchi, Akihiro,Kambara, Yui,Hanzawa, Yuji
supporting information, p. 2672 - 2675 (2013/07/19)
The metal-free [2 + 2 + 1] annulation of alkynes, nitriles, and O-atoms for the regioselective assembly of 2,4-disubstituted and 2,4,5-trisubstituted oxazole compounds has been achieved by the use of PhIO with TfOH or Tf 2NH. The present reaction could be applied to a facile synthesis of an anti-inflammatory drug.
Effects of base, electrophile, and substrate on the selective alkylation of heteroaromatic systems
Smith, Thomas E.,Mourad, Michelle S.,Velander, Alan J.
, p. 1211 - 1217 (2007/10/03)
Several heteroaromatic systems, including oxazoles, pyrazoles, and thiophenes, are regioselectively alkylated using lithium diethylamide. Effects of substrate, base, and electrophile on the selectivity of this process are surveyed and interpreted.
