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Updated: Jun 21, 2026

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
Published on: August 12, 2019
Solvent-promoted and -controlled aza-Michael reaction with aromatic amines
Kavita De1, Julien Legros, Benoit Crousse
1Laboratoire BioCIS-CNRS, Faculté de Pharmacie, Univ Paris Sud, rue JB Clément, F-92296 Châtenay-Malabry, France.
Abstract:
1,4-Addition of anilines onto Michael acceptors proceeds easily in specific polar protic solvents, without any promoting agent. According to the solvent and to the electrophile, the selectivity of the reaction can be finely tuned. With methyl acrylate as electrophile, only monoaddition takes place in water, while the diadduct is yielded in hexafluoroisopropyl alcohol (HFIP). The use of methyl vinyl ketone as a partner affords the monoadduct in water, the diadduct in trifluoroethanol (TFE), and the quinoline in HFIP.
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