214778-19-5

Upstream product

• 54797-42-1 2-oxo-2-phenylethyl propionate 
• 20662-90-2 2-methyl-4-phenyloxazole 
• 74-88-4 methyl iodide 
• 333-27-7 methyl trifluoromethanesulfonate 
• 536-74-3 phenylacetylene 
• 107-12-0 propiononitrile 
• 613-91-2 acetophenone oxime 

Relevant academic research and scientific papers

Metal-free syntheses of oxazoles and their analogues based on λ3-iodane-mediated cycloisomerization/functionalization reactions or [2+2+1] cycloaddition type reactions

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.

Iodine(III)-Catalyzed Formal [2 + 2 + 1] Cycloaddition Reaction for Metal-Free Construction of Oxazoles

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.

Copper-catalyzed direct synthesis of iodoenamides from ketoximes

Iodide in copper's pathway: A new, efficient, and practical copper-catalyzed synthesis of Z-iodoenamides from readily available ketoximes has been developed (see scheme). The reaction was believed to proceed through a single-electron-transfer pathway. The corresponding Z-iodoenamides have been applied to the synthesis of substituted oxazoles, dienes, β-phenoxyl enamides, eneynes, β-acylenamides, and pyrroles (DCE=1,2-dichloroethane). Copyright

Metal-free [2 + 2 + 1] annulation of alkynes, nitriles, and oxygen atoms: Iodine(III)-mediated synthesis of highly substituted oxazoles

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

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.

Selective lithiation of 2-methyloxazoles. Applications to pivotal bond constructions in the phorboxazole nucleus

(equation presented) R = Alkyl, Vinyl, Aryl 6:7 >95:5 The lithiation of 2-methyloxazoles with alkyllithium and hindered lithium amide bases generally results in the competitive formation of a mixture of 5-lithio-and 2-(lithiomethyl)oxazole isomers. Herein a synthetically useful lithiation method which allows for the selective formation of 2-(lithiomethyl)oxazole is described. Diethylamine has been found to be a kinetically competent proton source that will mediate the equilibration of the kinetically formed 5-lithiooxazole to its more stable 2-(lithiomethyl)oxazole counterpart. Application of this metalation strategy with lithium diethylamide to two important bond constructions relevant to a projected phorboxazole synthesis is presented.

Convenient syntheses of 2-alkyl(Aryl)-4,5-diphenyloxazoles and 2-alkyl(Aryl)-4-phepyloxazoles

The synthetic methods to prepare 2-alkyl(aryl)-4,5-diphenyloxazoles and 2-alkyl(aryl)-4-phenyloxazoles were improved on the basis of a mechanistic study of oxazole formation from α-hydroxy ketones (carboxylic esters of benzoin and phenacyl alcohols). By these methods, seven trisubstituted oxazoles and twelve disubstituted oxazoles of the title compounds were prepared.