Indexed on: 11 Jul '17Published on: 05 Jul '17Published in: Advanced Synthesis & Catalysis
The efficiency of N,N-dimethylformamide (DMF) in the N-heterocyclic carbene-catalyzed Mannich reaction for the synthesis of β-amino ketones has been demonstrated. This strategy involves oxidative coupling of aryl methyl ketones and 2-aminopyridines in the presence of DMF. The reaction does not require pre-functionalization of the substrates, thus making it a practically applicable approach for the generation of β-amino ketones. The reaction requires the use of tin(II) chloride dihydrate (SnCl2⋅2 H2O) as Lewis acid in the presence of tert-butyl hydroperoxide (TBHP) as the oxidant. The reaction was tolerant to several aryl methyl ketones, including 2-acetylnaphthalene and acetylthiophene. Various substituted 2-aminopyridines react with acetophenone to give the desired β-amino ketones in good yields.
Indexed on: 01 May '81
Published on: 01 May '81 in Chemistry of Heterocyclic Compounds