926013-65-2Relevant academic research and scientific papers
A novel metal-free synthesis of thiazole-substituted α-hydroxy carbonyl compounds and 2-alkenylthiazoles from thiazole N-oxides and olefins
Li, Hui,Zhang, Juan,Zhang, Yanqiu,Wang, Jiayi,Song, Gonghua
, (2019)
A metal-free and highly atom-economic synthesis of thiazole-substituted α-hydroxy carbonyl compounds has been developed. Catalyzed by 5 mol% of p-toluenesulfonic acid (TsOH), a variety of thiazole-substituted α-hydroxy carbonyl compounds were obtained in
Coupling-isomerization synthesis of chalcones
Braun, Roland U.,Ansorge, Markus,Mueller, Thomas J. J.
, p. 9081 - 9094 (2007/10/03)
The Sonogashira coupling of electron-deficient (hetero)aryl halides 1 and (hetero)aryl or alkenyl 1-propargyl alcohols 2 does not terminate at the stage of the expected internal propargyl alcohols, but rather gives rise to the formation of α,β-unsaturated ketones 3 with a variety of acceptor substituents. This new domino reaction, a coupling-isomerization reaction (CIR), can be rationalized as a sequence of rapid Pd/Cu-catalyzed alkynylation followed by a slow amine-base-catalyzed propargyl alcohol-enone isomerization. Performing the CIR in deuterated protic solvents or with a selectively deuterated propargyl alcohol revealed that the base-catalyzed isomerization step proceeds through a formal 1,3-H shift with minimal H/D exchange with the surrounding solvent. Additionally, 19F NMR kinetic measurements on the isomerization step with the fluorinated propargyl alcohol 4r support the mechanistic rationale.
