α-溴代烯酮与 1,2-二胺的反应。通过重排实现 3-(三氟甲基)哌嗪-2-酮的级联组装。
Reaction of α-bromo enones with 1,2-diamines. Cascade assembly of 3-(trifluoromethyl)piperazin-2-ones via rearrangement.
机构信息
A. E. Favorsky Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk 664033, Russia.
出版信息
Org Lett. 2013 Jun 7;15(11):2726-9. doi: 10.1021/ol401041f. Epub 2013 May 30.
A facile one-pot synthesis of 3-trifluoromethylated piperazin-2-ones has been achieved by the treatment of trifluoromethyl 2-bromo enones with N,N'-disubstituted ethylenediamines in trifluoroethanol. The mechanism of this unexpected reaction is discussed in terms of multistep processes involving formation of captodative aminoenone as a key intermediate. The unique influence of trifluoromethyl group on the reaction path was demonstrated.
通过三氟乙醇中用 N,N'-二取代乙二胺处理三氟甲基 2-溴烯酮，实现了 3-三氟甲基哌嗪-2-酮的简便一锅合成。根据涉及形成加托达ative 氨基烯酮作为关键中间体的多步过程讨论了这种意外反应的机理。证明了三氟甲基对反应途径的独特影响。
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