Highly efficient and diastereoselective synthesis of new pyrazolylpyrrolizine and pyrazolylpyrrolidine derivates by a three-component domino process

Molecules. 2014 Apr 4;19(4):4284-300. doi: 10.3390/molecules19044284.

Abstract

Diastereoselective reactions between 4-formylpyrazoles, N-substituted maleimides and glycine derivates led to new series of pyrazolyldipyrrolo [3,4-a:3',4'-f]pyrrolizines and pyrazolylpyrrolo[3,4-c]pyrroles in good yields. The reactions proceeded by a domino process through azomethine ylides formed in situ via a 1,3-dipolar cycloaddition reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azo Compounds / chemistry
  • Catalysis
  • Cycloaddition Reaction
  • Glycine / analogs & derivatives
  • Maleimides / chemistry
  • Molecular Structure
  • Pyrroles / chemical synthesis*
  • Stereoisomerism
  • Thiosemicarbazones / chemistry

Substances

  • Azo Compounds
  • Maleimides
  • Pyrroles
  • Thiosemicarbazones
  • azomethine
  • Glycine