65219-93-4Relevant articles and documents
Self-condensation of (β-Alkoxycarbonylalkylidene)ammonium Salts
Boehme, Horst,Graetz, Jochen Graetzel von,Martin, Fred,Matusch, Rudolf,Nehne, Joerg
, p. 394 - 402 (2007/10/02)
Iminium chlorides or trifluoroacetates of type 2, formed by protonation of β-(alkoxycarbonyl)-enamines 1, have been proved to undergo condensation to give derivatives of 4-alkyl-2-amino-6-hydroxybenzoic acid 6 via elimination of ammonium salt and alcohol.The structures of 6 had been established by spectroscopic data as well as by further reactions.The range of application of this condensation reaction has been studied and the mechanism is discussed.In the primary step presumably a nucleophilic attack on the alkoxycarbonyl group of the iminium salt 2 takes place by the enamine 1 present in the equilibrium.Analogous reactions are also found for homologues of the enamine 1 (e.g. 11, 13 and 17) to give the condensation products 12, 14, 15, and 20.