3 years ago

Synergistic I2/Amine Promoted Povarov-Type Reaction for the Synthesis of 2-Acyl-3-aryl(alkyl)quinolines Using Aryl(alkyl)acetaldehydes as Alkene Surrogates

Synergistic I2/Amine Promoted Povarov-Type Reaction for the Synthesis of 2-Acyl-3-aryl(alkyl)quinolines Using Aryl(alkyl)acetaldehydes as Alkene Surrogates
An-Xin Wu, Xia Wu, Xiao Geng, Peng Zhao, Jingjing Zhang, Yan-Dong Wu
A synergistic I2/amine promoted formal [4 + 2] cycloaddition of methyl ketones, arylamines, and aryl(alkyl)acetaldehydes as alkene surrogates has been established. This protocol allowed the modular synthesis of various 2-acyl-3-aryl(alkyl)quinolines, rather than 2,4-substituted quinolines. Notably, the arylamines not only participated as reactants in this reaction but also acted as indispensable catalysts to promote enamine formation. Moreover, mechanistic investigation suggested that the reaction occurred via an iodination/Kornblum oxidation/Povarov/aromatization sequence.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01686

DOI: 10.1021/acs.orglett.7b01686

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.