Accessing Polysubstituted NH Pyrroles from Nitroalkenes via [4+2]‐Cycloaddition/Reductive Ring Contraction Strategy

Author:

Pospelov Evgeny V.1ORCID,Zhirov Alexander V.12,Kamidolla Baglan13,Sukhorukov Alexey Yu.1ORCID

Affiliation:

1. Laboratory of organic and metal-organic nitrogen-oxygen systems N. D. Zelinsky Institute of Organic Chemistry Leninsky prospect, 47 Moscow 119991 Russia

2. Department of Chemistry M. V. Lomonosov Moscow State University Leninskie gory, 1, str. 3 Moscow 119991 Russia

3. Higher Chemical College D. Mendeleev University of Chemical Technology of Russia Miusskaya sq., 9 Moscow 125047 Russia

Abstract

AbstractA 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.

Funder

Russian Science Foundation

Publisher

Wiley

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