Aminations and arylations by direct C-O activation for the design of 7,8-dihydro-6 H -5,8-ethanopyrido[3,2- d ]pyrimidines.
Mazarine LaurentStéphane BostynMathieu MarchivieYves RobinSylvain RoutierFrédéric BuronPublished in: RSC advances (2021)
The design of some novel disubstituted 7,8-dihydro-6 H -5,8-ethanopyrido[3,2- d ]pyrimidine derivatives is reported. The series was developed from quinuclidinone, which afforded versatile platforms bearing one lactam function in position C -2 that were then used to create C-N or C-C bonds for S N Ar or palladium-catalyzed cross-coupling reactions by in situ C-O activation. The reaction conditions were optimized under microwave irradiation, and a wide range of amines or boronic acids were used to determine the scope and limitations of each method. To complete this study, the X-ray crystallographic data of 7,8-dihydro-6 H -5,8-ethanopyrido[3,2- d ]pyrimidine derivative 49 were used to formally establish the structures of the products.