Aminations and arylations by direct C-O activation for the design of 7,8-dihydro-6H-5,8-ethanopyrido[3,2-d]pyrimidines.

ABSTRACT: The design of some novel disubstituted 7,8-dihydro-6H-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-6H-5,8-ethanopyrido[3,2-d]pyrimidine derivative 49 were used to formally establish the structures of the products.

SUBMITTER: Laurent M 

PROVIDER: S-EPMC9033610 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature