Abstract
A practical benzannulation method to prepare variously substituted aryl amines and sulfides was developed. The approach involves a Michael-aldol reaction of beta-keto sulfones with enones followed by a subsequent condensation of the initial adduct with various amines. The base-induced Michael-aldol cascade proceeds smoothly with a number of different beta-keto sulfones, affording the adducts as single diastereomers. Heating the resulting Michael-aldol product with an amine in toluene at 120 degrees 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.
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