title: A mild method for the synthesis of carbamate-protected guanidines using the Burgess reagent.
abstract: A simple method for the synthesis of carbamate-protected guanidines from primary amines is described. A variety of thioureas derived from primary amines and isothiocyanates react with the Burgess reagent to give the corresponding guanidines via either a stepwise or one-pot procedure. By tuning the carbamoyl units of isothiocyanates and the Burgess reagent, differentially N,N'-diprotected guanidines can be obtained. Selective deprotection of the products affords N-monoprotected guanidines.
authors.affiliation: Chemical Development Center, CMC Development Laboratories, Shionogi & Co., Ltd., 3-1-1, Futaba-cho, Toyonaka-shi, Osaka 561-0825, Japan.
authors.forename: Toshikatsu
authors.initials: T
authors.lastname: Maki
authors.forename: Takayuki
authors.initials: T
authors.lastname: Tsuritani
authors.forename: Tatsuro
authors.initials: T
authors.lastname: Yasukata
mesh_terms: D000588:Amines / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry*; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D017879:Isothiocyanates / Q000737:chemistry; D015394:Molecular Structure; D013890:Thiourea / Q000737:chemistry
chemical_list: D000588:Amines; D002219:Carbamates; D006146:Guanidines; D007202:Indicators and Reagents; D017879:Isothiocyanates; D013890:Thiourea