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Synthesis and Reactivity of 1,4‐Ethano‐1,5‐Naphthyridine Derivatives Using Microwave Activation or Flow Chemistry
Author(s) -
Laurent Mazarine,
Vatinel Rodolphe,
Bostyn Stéphane,
Routier Sylvain,
Buron Frédéric
Publication year - 2025
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202401443
Subject(s) - chemistry , reactivity (psychology) , flow chemistry , microwave chemistry , microwave , combinatorial chemistry , continuous flow , microwave irradiation , organic chemistry , catalysis , medicine , physics , alternative medicine , pathology , quantum mechanics , mechanics
The design of some novel disubstituted 3,4‐dihydro‐2 H ‐1,4‐ethano‐1,5‐naphthyridine derivatives is reported under classical and flow methodologies. The series are developed from quinuclidinone, which afford versatile platforms bearing one lactam function in position C ‐2 that is then used to create C─N bond using the Chan–Lam coupling reaction or in situ C─O bond activation via palladium‐catalyzed cross‐coupling reactions. The conditions are optimized and a wide range of boronic acids are used to determine the scope and limitations of each method. To complete this study, a flow Suzuki–Miyaura process is established to afford polyfunctionalized 1,4‐ethano‐1,5‐naphthyridine derivatives in high yields with a very efficient process (10 min).