We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
Accessing Polysubstituted NH Pyrroles from Nitroalkenes via [4+2]‐Cycloaddition/Reductive Ring Contraction Strategy.
- Authors
Pospelov, Evgeny V.; Zhirov, Alexander V.; Kamidolla, Baglan; Sukhorukov, Alexey Yu.
- Abstract
A novel two‐step access to polysubstituted pyrroles from nitroalkenes was developed. It involves [4+2]‐cycloaddition with enol ethers to give six‐membered cyclic nitronates followed by reductive ring contraction with Ra−Ni/AcOH or Ra−Ni/EtOH systems. The process is applicable to a variety of nitroalkenes and enol ethers bearing electron‐rich and electron‐poor substituents and functional groups. The anti‐inflammatory drug Bimetopyrol and its structural modifications were successfully synthesized by the strategy developed. The key side products were identified that provided an insight into the mechanism of the developed reductive ring contraction to pyrroles.
- Subjects
PYRROLES; NITROALKENES; FUNCTIONAL groups; RING formation (Chemistry)
- Publication
European Journal of Organic Chemistry, 2024, Vol 27, Issue 30, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202400627