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

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 p...

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Detalles Bibliográficos
Autores principales: Laurent, Mazarine, Bostyn, Stéphane, Marchivie, Mathieu, Robin, Yves, Routier, Sylvain, Buron, Frédéric
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9033610/
https://www.ncbi.nlm.nih.gov/pubmed/35479218
http://dx.doi.org/10.1039/d1ra03092b
Descripción
Sumario: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.