118987-97-6Relevant academic research and scientific papers
A highly efficient multicomponent synthesis of pyridones and pyrimidones by a [2+2+2] strategy
Ghosez, Leon,Jnoff, Eric,Bayard, Philippe,Sainte, Francy,Beaudegnies, Renaud
, p. 3387 - 3400 (2007/10/03)
The reaction of N-silylated iminoethers with 2-substituted acetyl chlorides yields activated 2-azadienes. These were shown to react with electron-deficient acetylenic dienophiles to yield pyridones. They also react with quinones to give the corresponding aromatized cycloadducts in good yields. The reaction of 2-azadienes with activated nitriles provided a very practical route towards polysubstituted pyrimidones. A multicomponent protocol is reported which combines a N-t-butyldimethylsilyl iminoether, an acetyl chloride derivative and a dienophile in the presence of triethylamine without isolation of any intermediate. This provides an extremely practical and versatile route to various mono- and polycyclic azaaromatics with a predictable substitution pattern. Yields ranged from 43% to 94% for the complete sequence.
A DIELS-ALDER ROUTE TOWARDS PYRIMIDIN-4-ONES
Bayard, Ph.,Sainte, F.,Beaudegnies, R.,Ghosez, L.
, p. 3799 - 3802 (2007/10/02)
N-acylimidates 4 are readily sylilated with t-butyldimethylsilyl triflate in the presence of triethylamine to give 2-aza-1,3-dienes 1.These react with activated nitriles to yield pyrimidin-4-ones 6.
