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Rh III ‐Catalysed Hydrazine‐Directed C(sp 2 )–H Amination of Phenidones with N ‐Alkyl‐ O ‐benzoyl‐hydroxylamines
Author(s) -
Xue Yu,
Fan Zhoulong,
Jiang Xiaolong,
Wu Kui,
Wang Meining,
Ding Chunyong,
Yao Qizheng,
Zhang Ao
Publication year - 2014
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.201402999
Subject(s) - chemistry , amination , hydrazine (antidepressant) , alkyl , moiety , functional group , medicinal chemistry , organic chemistry , catalysis , chromatography , polymer
A Rh III ‐catalysed ortho C–H amination of phenidones under mild conditions was developed using N ‐alkyl‐ O ‐benzoyl‐hydroxylamines as aminating agents, and with a cyclic hydrazine moiety as a directing group, yields of up to 97 % and a high functional group tolerance were observed. This strategy offers an alternative route for the synthesis of amino analogues of the 5‐lipoxygenase inhibitor phenidone, and the products are valuable for further functional group transformations.