American Chemical Society (ACS)
Organic Letters
,  volume 15 ,  issue 11 ,  pages 2726-2729

Reaction of α-Bromo Enones with 1,2-Diamines. Cascade Assembly of 3-(Trifluoromethyl)piperazin-2-ones via Rearrangement

Publication type: Journal Article
Publication date: 2013-05-30
American Chemical Society (ACS)
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
DOI:  10.1021/ol401041f
PubMed ID:  23718550
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
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.
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GOST Copy
Rulev A. Y. et al. Reaction of α-Bromo Enones with 1,2-Diamines. Cascade Assembly of 3-(Trifluoromethyl)piperazin-2-ones via Rearrangement // Organic Letters. 2013. Vol. 15. No. 11. pp. 2726-2729.
GOST all authors (up to 50) Copy
Rulev A. Y., Muzalevskiy V. M., Kondrashov E. V., Ushakov I., Romanov A. R., Khrustalev V. N., Nenajdenko V. G. Reaction of α-Bromo Enones with 1,2-Diamines. Cascade Assembly of 3-(Trifluoromethyl)piperazin-2-ones via Rearrangement // Organic Letters. 2013. Vol. 15. No. 11. pp. 2726-2729.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1021/ol401041f
UR - https://doi.org/10.1021/ol401041f
TI - Reaction of α-Bromo Enones with 1,2-Diamines. Cascade Assembly of 3-(Trifluoromethyl)piperazin-2-ones via Rearrangement
T2 - Organic Letters
AU - Rulev, Alexander Yu.
AU - Muzalevskiy, Vasily M.
AU - Kondrashov, Evgeniy V
AU - Ushakov, Igor
AU - Romanov, Alexey R
AU - Khrustalev, Victor N.
AU - Nenajdenko, Valentine G.
PY - 2013
DA - 2013/05/30
PB - American Chemical Society (ACS)
SP - 2726-2729
IS - 11
VL - 15
PMID - 23718550
SN - 1523-7060
SN - 1523-7052
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2013_Rulev,
author = {Alexander Yu. Rulev and Vasily M. Muzalevskiy and Evgeniy V Kondrashov and Igor Ushakov and Alexey R Romanov and Victor N. Khrustalev and Valentine G. Nenajdenko},
title = {Reaction of α-Bromo Enones with 1,2-Diamines. Cascade Assembly of 3-(Trifluoromethyl)piperazin-2-ones via Rearrangement},
journal = {Organic Letters},
year = {2013},
volume = {15},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/ol401041f},
number = {11},
pages = {2726--2729},
doi = {10.1021/ol401041f}
}
MLA
Cite this
MLA Copy
Rulev, Alexander Yu., et al. “Reaction of α-Bromo Enones with 1,2-Diamines. Cascade Assembly of 3-(Trifluoromethyl)piperazin-2-ones via Rearrangement.” Organic Letters, vol. 15, no. 11, May. 2013, pp. 2726-2729. https://doi.org/10.1021/ol401041f.