Iron-Catalyzed Cyclization of Ketoxime Carboxylates and Tertiary Anilines for the Synthesis of Pyridines

A novel and efficient iron-catalyzed cyclization of ketoxime carboxylates and N,N-dialkylanilines for the modular synthesis of diverse pyridines was developed. The reaction was initiated by Fe-catalyzed N–O bond cleavage of ketoxime carboxylates in the presence of tertiary anilines. The methylene ca...

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Bibliographic Details
Published in:Organic letters 2016-03, Vol.18 (5), p.1194-1197
Main Authors: Zhao, Mi-Na, Ren, Zhi-Hui, Yu, Le, Wang, Yao-Yu, Guan, Zheng-Hui
Format: Article
Language:English
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Summary:A novel and efficient iron-catalyzed cyclization of ketoxime carboxylates and N,N-dialkylanilines for the modular synthesis of diverse pyridines was developed. The reaction was initiated by Fe-catalyzed N–O bond cleavage of ketoxime carboxylates in the presence of tertiary anilines. The methylene carbon on N,N-dialkylanilines functioned as a source of one-carbon synthon in the reaction. The reaction used readily available starting materials, tolerated various functional groups, and afforded 2,4-disubstituted and 2,4,6-trisubstituted pyridines in good to high yields under mild conditions.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b00326