TFA-sensitive arylsulfonylthiourea-assisted synthesis of N,N'-substituted guanidines

J Org Chem. 2003 Feb 21;68(4):1611-4. doi: 10.1021/jo026807m.

Abstract

An efficient synthesis of N,N'-substituted guanidine derivatives was developed via an aromatic sulfonyl-activated thiourea intermediate. The use of certain aromatic sulfonamides, such as PbfNH(2), as the key reagent to incorporate a TFA-labile guanidine protection group greatly facilitates solid-phase synthesis of N,N'-substituted guanidine compounds.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Catalysis
  • Combinatorial Chemistry Techniques
  • Guanidines / chemical synthesis*
  • Indicators and Reagents
  • Molecular Structure
  • Sulfonamides / chemistry
  • Thiourea / chemistry*
  • Trifluoroacetic Acid / chemistry*

Substances

  • Guanidines
  • Indicators and Reagents
  • Sulfonamides
  • Trifluoroacetic Acid
  • Thiourea