Reaction of α-bromo enones with 1,2-diamines. Cascade assembly of 3-(trifluoromethyl)piperazin-2-ones via rearrangement.

doi:10.1021/ol401041f

Paper

Reaction of α-bromo enones with 1,2-diamines. Cascade assembly of 3-(trifluoromethyl)piperazin-2-ones via rearrangement.

Published May 30, 2013 · A. Rulev, V. M. Muzalevskiy, E. Kondrashov

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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.

Study Snapshot

This study demonstrates a facile one-pot synthesis of 3-trifluoromethylated piperazin-2-ones by treating trifluoromethyl 2-bromo enones with N,N'-disubstituted ethylenediamines in trifluoroethanol, highlighting

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Reaction of α-bromo enones with 1,2-diamines. Cascade assembly of 3-(trifluoromethyl)piperazin-2-ones via rearrangement.

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References

Dissecting alkynes: full cleavage of polarized C≡C moiety via sequential bis-Michael addition/retro-Mannich cascade.

The reaction of diaryl ketoalkynes with 1,2-diamino ethane leads to the full cleavage of the triple bond, forming acetophenone and imidazoline fragments, with both amines playing a role in the fragmentation process.

Direct Access to Cumbersome Aminated Quaternary Centers by Hyperbaric Aza‐Michael Additions

Hyperbaric aza-Michael additions efficiently produce cumbersome -aminesters with direct connections to quaternary carbon atoms, offering potential for new synthesis strategies.

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2-(Trifluoromethyl)piperazine: Synthesis and characterization using NMR and X-ray photoelectron spectroscopy

2-(trifluoromethyl)piperazine (1) has a CF3 group in an equatorial position, causing a secondary chemical shift of 1.5 eV on its nearest neighbor carbon atom.

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Haloalkenes activated by geminal groups in reactions with nitrogen nucleophiles show a dependence on the nature of the nucleophile and substrate, as well as reaction conditions, potentially enabling nucleophilic substitution of vinylic halogen atoms in alkenes.

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