1191924-78-3Relevant articles and documents
A benzannulation protocol to prepare substituted aryl amines using a michael-aldol reaction of β-keto sulfones
Kiren, Sezgin,Padwa, Albert
experimental part, p. 7781 - 7789 (2009/12/30)
(Chemical Equation Presented) A practical benzannulation method to prepare variously substituted aryl amines and sulfides was developed. The approach involves a Michael-aldol reaction of β-keto sulfones with enones followed by a subsequent condensation of the initial adduct with various amines. The base-induced Michaelaldol cascade proceeds smoothly with a number of different β-keto sulfones, affording the adducts as single diastereomers. Heating the resulting Michael-aldol product with an amine in toluene at 120°C results in the formation of a transient enamine, which then undergoes loss of phenyl sulfenic acid to furnish the aromatized amine in good yield. A related reaction also occurred when the Michael-aldol product was heated with thiols or alcohols, giving rise to aryl-substituted sulfides or ethers.