40227-86-9Relevant academic research and scientific papers
Ultrasound-Promoted Synthesis of 4-Pyrimidinols and Their Tosyl Derivatives
Vidal, Matías,García-Arriagada, Macarena,Rezende, Marcos Caroli,Domínguez, Moisés
, p. 4246 - 4252 (2016)
Ultrasound irradiation promoted the cyclocondensation of β-keto esters and amidines in good to excellent yields to form sixteen highly substituted 4-pyrimidinols. Tosylation of these compounds, in another ultrasound-promoted conversion, formed 4-pyrimidyl tosylates in high yields. The use of the developed protocol as an alternative route to 4-arylpyrimidines was illustrated with three examples of the Suzuki-Miyaura cross-coupling of the prepared tosylates with phenylboronic acid.
Heteroaromatic tosylates as electrophiles in regioselective Mizoroki-Heck-coupling reactions with electron-rich olefins
Gogsig, Thomas M.,Lindhardt, Anders T.,Dekhane, Mouloud,Grouleff, Julie,Skrydstrup, Troels
supporting information; experimental part, p. 5950 - 5955 (2010/02/28)
Heteroaromatic 2-pyridyl tosylates were successfully applied as electrophiles in palladium(0)-catalyzed Mizoroki-Heck-coupling reactions to electron-rich olefins with complete aregioselectivity. This protocol represents a general strategy for the application of pyridyl tosylates and mesylates in the Mizoroki-Heck coupling. The catalytic system also proved adaptable to changes in the heteroaromatic core as well as large-scale applications. Finally, the synthetic utility of the functionalized α-heteroarylvinyl amides was established providing straightforward access to highly functionalized heteroaromatic compounds including chiral benzylic amide derivatives.
