title: Solvent-promoted and -controlled aza-Michael reaction with aromatic amines.
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.
authors.affiliation: Laboratoire BioCIS-CNRS, Faculté de Pharmacie, Univ Paris Sud, rue JB Clément, F-92296 Châtenay-Malabry, France.
authors.forename: Kavita
authors.initials: K
authors.lastname: De
authors.forename: Julien
authors.initials: J
authors.lastname: Legros
authors.forename: Benoit
authors.initials: B
authors.lastname: Crousse
authors.forename: Danièle
authors.initials: D
authors.lastname: Bonnet-Delpon
mesh_terms: D000179:Acrylates / Q000737:chemistry; D000478:Alkylation; D000588:Amines / Q000737:chemistry*; D001372:Aza Compounds / Q000737:chemistry*; D002074:Butanones / Q000737:chemistry; D012997:Solvents / Q000737:chemistry*
chemical_list: D000179:Acrylates; D000588:Amines; D001372:Aza Compounds; D002074:Butanones; D012997:Solvents; C057920:3-buten-2-one; C035956:methyl acrylate