Regioselective multicomponent sequential synthesis of hydantoins

Org Biomol Chem. 2012 Dec 28;10(48):9538-55. doi: 10.1039/c2ob26498f. Epub 2012 Oct 17.

Abstract

The development of new practical and green methods for the synthesis of small heterocycles is an attractive area of research due to the well-known potential of heterocyclic small molecule scaffolds in the drug discovery process. Herein we report a one-pot, three-component sequential procedure for the synthesis of diversely 1,3,5- and 1,3,5,5-substituted hydantoins, in high yields and very mild conditions, using readily accessible starting materials such as azides, iso(thio)cyanates and substituted α-halo-acetic carboxylic acids. This methodology is especially convenient for the synthesis of spiro-hydantoins, which are particularly interesting bioactive compounds in medicinal chemistry.

MeSH terms

  • Azides / chemistry
  • Carboxylic Acids / chemistry
  • Chemistry Techniques, Synthetic / methods*
  • Chemistry, Pharmaceutical
  • Drug Discovery / methods*
  • Hydantoins / chemical synthesis*
  • Hydantoins / chemistry
  • Hydrocarbons, Halogenated / chemistry
  • Isocyanates / chemistry
  • Molecular Structure
  • Thiocyanates / chemistry

Substances

  • Azides
  • Carboxylic Acids
  • Hydantoins
  • Hydrocarbons, Halogenated
  • Isocyanates
  • Thiocyanates