Reaction of 伪-Bromo Enones with 1,2-Diamines. Cascade Assembly of 3-(Trifluoromethyl)piperazin-2-ones via Rearrangement
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- 作者：Alexander Yu. Rulev ; Vasiliy M. Muzalevskiy ; Evgeniy V. Kondrashov ; Igor A. Ushakov ; Alexey R. Romanov ; Victor N. Khrustalev ; Valentine G. Nenajdenko
- 刊名：Organic Letters
- 出版年：2013
- 出版时间：June 7, 2013
- 年：2013
- 卷：15
- 期：11
- 页码：2726-2729
- 全文大小：240K
- 年卷期：v.15,no.11(June 7, 2013)
- ISSN：1523-7052
文摘
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鈥?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.