Tetrahedron
Tetrahedron
5 years ago

Reduction of imidazolium salts – An approach to diazocines and diazocanes

Reduction of imidazolium salts – An approach to diazocines and diazocanes
A convenient approach to diazocine derivatives 8,9 starting from 1,2-polymethyle-neimidazolium salts 4 was developed. The polymethylenimidazolium salts 4 are partially reduced with sodium borohydride in DMF to give 5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-a]imidazoles 5 or under more forcing conditions – (sodium triacetoxyborohydride in acetic acid) with cleavage of the endocyclic CN bond affording diamines 6. Tertiary salts 7 readily prepared from compounds 5 react with NaBH4 and KCN nucleophiles with cleavage of the endocyclic NC bond to form diazocine derivatives 8,9.

Publisher URL: www.sciencedirect.com/science

DOI: S0040402017310906

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.