Regioselective synthesis of novel spiropyrrolidines and spirothiapyrrolizidines through multicomponent 1,3-dipolar cycloaddition reaction of azomethine ylides

J Comb Chem. 2010 Sep 13;12(5):633-7. doi: 10.1021/cc100035q.

Abstract

A series of novel spiropyrrolidines and spirothiapyrrolizidines were synthesized via a three-component 1,3-dipolar cycloaddition reaction of isatin or acenaphthenequinone, sarcosine or thiaproline and 4-hydroxy-6-methyl-3-((E)-3-phenylacryloyl)-2H-pyran-2-ones in refluxing ethanol. Advantages of this method include the availability of starting materials, mild reaction conditions, high yields, and the complete regioselectivity observed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azo Compounds / chemistry*
  • Combinatorial Chemistry Techniques
  • Crystallography, X-Ray
  • Cyclization
  • Models, Molecular
  • Molecular Structure
  • Pyrrolidines / chemical synthesis*
  • Pyrrolidines / chemistry
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Stereoisomerism
  • Thiazolidines / chemical synthesis*
  • Thiazolidines / chemistry
  • Thiosemicarbazones / chemistry*

Substances

  • Azo Compounds
  • Pyrrolidines
  • Spiro Compounds
  • Thiazolidines
  • Thiosemicarbazones
  • azomethine