Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 14, Pages 2369-2374Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201700125
Keywords
beta-amino ketones; 2-aminopyridines; Mannich reaction; N,N-dimethylformamide; N-heterocyclic carbenes; oxidation
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Funding
- DST, SERB, New Delhi [SB/FT/CS-108/2012]
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The efficiency of N,N-dimethylformamide (DMF) in the N-heterocyclic carbene-catalyzed Mannich reaction for the synthesis of beta-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 beta-amino ketones. The reaction requires the use of tin(II) chloride dihydrate (SnCl2 center dot 2H(2)O) 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 beta-amino ketones in good yields.
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