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Co(II)‐Catalyzed Oxidation of N,N ‐Dimethylaminoethanol: An Efficient Synthesis of Unsymmetrical (2,4‐) and Symmetrical (2,6‐) Diarylpyridines through Annulation of Aromatic Ketones with a Nitrogen Source
Author(s) -
Qin Zemin,
Zhang Ruiqin,
Ma Yongmin,
Li Fanzhu
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202100353
Subject(s) - annulation , chemistry , synthon , catalysis , steric effects , nitrogen , carbon fibers , medicinal chemistry , organic chemistry , combinatorial chemistry , materials science , composite number , composite material
An efficient and facile synthesis of 2,4‐ and 2,6‐diarylpyridines has been developed. It involves one‐pot [2+2+1+1] pseudo four‐component annulation of aromatic ketones, a nitrogen source and a carbon donor. N,N ‐Dimethylaminoethanol is oxidized in the presence of Co(II) to provide a carbon synthon. Two C−C and two C−N bonds are formed during the oxidative annulation process. The products are strictly controlled due to the steric hindrance: 2,4‐diarylpyridines are afforded effectively with small ketones while 2,6‐diaryl analogues predominate when bulky ketones are employed.