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

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

The design of some novel disubstituted 7,8-dihydro-6 -5,8-ethanopyrido[3,2- ]pyrimidine derivatives is reported. The series was developed from quinuclidinone, which afforded versatile platforms bearing one lactam function in position -2 that were then used to create C-N or C-C bonds for S Ar or pall...

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Bibliographic Details
Published in:RSC advances 2021-05, Vol.11 (32), p.19363-19377
Main Authors: Laurent, Mazarine, Bostyn, Stéphane, Marchivie, Mathieu, Robin, Yves, Routier, Sylvain, Buron, Frédéric
Format: Article
Language:eng
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Summary:The design of some novel disubstituted 7,8-dihydro-6 -5,8-ethanopyrido[3,2- ]pyrimidine derivatives is reported. The series was developed from quinuclidinone, which afforded versatile platforms bearing one lactam function in position -2 that were then used to create C-N or C-C bonds for S Ar or palladium-catalyzed cross-coupling reactions by 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 -5,8-ethanopyrido[3,2- ]pyrimidine derivative 49 were used to formally establish the structures of the products.
ISSN:2046-2069
2046-2069