TFA-sensitive arylsulfonylthiourea-assisted synthesis of N,N'-substituted guanidines.
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.
Li
Jizhen
J
Biomolecular Structure Center, Department of Biochemistry, University of Washington, Seattle, Washington 98195, USA.
Zhang
Guangtao
G
Zhang
Zhongsheng
Z
Fan
Erkang
E
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006146:Guanidines / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D015394:Molecular Structure; D013449:Sulfonamides / Q000737:chemistry; D013890:Thiourea / Q000737:chemistry*; D014269:Trifluoroacetic Acid / Q000737:chemistry*
D006146:Guanidines; D007202:Indicators and Reagents; D013449:Sulfonamides; D014269:Trifluoroacetic Acid; D013890:Thiourea