3 years ago

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

N-Heterocyclic Carbene-Catalyzed Mannich Reaction for the Synthesis of β-Amino Ketones: N,N-Dimethylformamide as Carbon Source
A. Tamil Selvi, Vellaisamy Sridharan, Subbiah Nagarajan, E. Sankari Devi, C. Uma Maheswari, Anitha Alanthadka
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.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/adsc.201700125

You might also like
Discover & Discuss Important Research

Keeping up-to-date with research can feel impossible, with papers being published faster than you'll ever be able to read them. That's where Researcher comes in: we're simplifying discovery and making important discussions happen. With over 19,000 sources, including peer-reviewed journals, preprints, blogs, universities, podcasts and Live events across 10 research areas, you'll never miss what's important to you. It's like social media, but better. Oh, and we should mention - it's free.

  • Download from Google Play
  • Download from App Store
  • Download from AppInChina

Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.