3 years ago

Isatin N,N′-Cyclic Azomethine Imine 1,3-Dipole and Base Catalyzed Michael Addition with β-Nitrostyrene via C3 Umpolung of Oxindole

Isatin N,N′-Cyclic Azomethine Imine 1,3-Dipole and Base Catalyzed Michael Addition with β-Nitrostyrene via C3 Umpolung of Oxindole
Lin Peng, Xiao Wang, Xiang-Jia Song, Li-Xin Wang, Lin Wu, Peng Yang, Hong-Xia Ren
A new isatin N,N′-cyclic azomethine imine 1,3-dipole was devised, and an unusual Michael addition with β-nitrostyrene catalyzed by tributylamine under mild conditions has been developed. The new reaction featured the C3 umpolung of oxindole and an unusual formation of double bond. Notably, this new synthon performed as a donor rather than an acceptor. This protocol provided a promising method for the preparation of various 3-aminooxindoles with good yields in moderate diastereoselectivities.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01063

DOI: 10.1021/acs.orglett.7b01063

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.