Tetrahedron
Tetrahedron
5 years ago

A flow strategy for the rapid, safe and scalable synthesis of N-H 1, 2, 3-triazoles via acetic acid mediated cycloaddition between nitroalkene and NaN3

A flow strategy for the rapid, safe and scalable synthesis of N-H 1, 2, 3-triazoles via acetic acid mediated cycloaddition between nitroalkene and NaN3
The N-unsubstituted 4-aryl-1H-1,2,3-triazoles were synthesized via the acetic acid promoted cycloaddition between β-nitrostyrenes with sodium azide under transition-metal-free conditions in a continuous flow microreactor. The continuous-flow microreactor provided a safe environment for the dangerous reagents NaN3 and nitroalkene, and offered such a rapid procedure that the triazoles were formed in less than 4 min. In addition, the excess sodium azide was quenched by the by-product HNO2 in the presence of acetic acid. The scale-up experiment proved again that the yield did not drop in the flow reaction. Moreover, the synthesis of N-unsubstituted 1,2,3-triazole was also explored via a one pot reaction with aldehyde, nitromethane and sodium azide, and this reaction was monitored with an “in-tube retention time gradient” (IT-RTG) technology, which may be a novel application of the continuous-flow microreactor.

Publisher URL: www.sciencedirect.com/science

DOI: S0040402017305665

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.