3 years ago

A Mild, Functional Group Tolerant Addition of Organozinc Nucleophiles to N-Activated Quinolines and Isoquinolines

A Mild, Functional Group Tolerant Addition of Organozinc Nucleophiles to N-Activated Quinolines and Isoquinolines
Neil A. Strotman, Jeanne Ho, Michael R. Luzung, Carlos A. Guerrero, Darryl D. Dixon, Martin D. Eastgate, Michael A. Schmidt, Sloan Ayers, Adrian Ortiz
An addition of organozinc nucleophiles to N-acyl activated quinolines and isoquinolines is described. Simple transmetalation with the corresponding Grignard reagents using ZnCl2 forms organozinc compounds which are functional group tolerant and stable to reactive acyl chloride reagents for extended periods. A wide variety of substrates which include reactive electron-withdrawing groups are well tolerated to form 2-substituted dihydroquinolines and dihydroisoquinolines. This methodology has been applied toward an improved synthetic route of uncialamycin and its analogs.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01882

DOI: 10.1021/acs.joc.7b01882

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.