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N-Heterocyclic Carbene-Catalyzed Mannich Reaction for the Synthesis of β-Amino Ketones: N,N-Dimethylformamide as Carbon Source

Research paper by Anitha Alanthadka, E. Sankari Devi, A. Tamil Selvi, Subbiah Nagarajan, Vellaisamy Sridharan, C. Uma Maheswari

Indexed on: 11 Jul '17Published on: 05 Jul '17Published in: Advanced Synthesis & Catalysis



Abstract

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.