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Iron‐Catalyzed Radical Relay Enabling the Modular Synthesis of Fused Pyridines from Alkyne‐Tethered Oximes and Alkenes
Author(s) -
Du Fei,
Li ShiJun,
Jiang Kun,
Zeng Rong,
Pan XiChun,
Lan Yu,
Chen YingChun,
Wei Ye
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202010752
Subject(s) - alkyne , chemistry , combinatorial chemistry , catalysis , functional group , substrate (aquarium) , cascade reaction , radical cyclization , molecule , hydrogen atom , stereochemistry , organic chemistry , group (periodic table) , oceanography , geology , polymer
We have rationally designed a new class of alkyne‐tethered oximes and applied them in an unprecedented iron‐catalyzed radical relay protocol for the rapid assembly of a wide array of structurally new and interesting fused pyridines. This method shows broad substrate scope and good functional‐group tolerance and enabled the synthesis of several biologically active molecules. Furthermore, the fused pyridines could be diversely functionalized through various simple transformations, such as cyclization, C−H alkylation, and a click reaction. DFT calculation studies indicate that the reactions involve cascade 1,5‐hydrogen atom transfer, 5‐ exo ‐dig radical addition, and cyclization processes. Moreover, preliminary biological investigations suggest that some of the fused pyridines exhibit good anti‐inflammatory activity by restoring the imbalance of inflammatory homeostasis of macrophages in a lipopolysaccharide‐induced model.