39259-22-8Relevant academic research and scientific papers
Novel linker for the solid-phase synthesis of guanidines
Josey, John A.,Tarlton, Catherine A.,Payne, Courtney E.
, p. 5899 - 5902 (1998)
A novel linker for the generation of alkyl-, acyl- and arylguanidines as an attachment point in solid phase synthesis has been developed. Introduction of a suitably functionalized thiourea to Wang resin via a carbamate linkage, followed by displacement of sulfur with a 1°or 2°amine affords resin bound guanidines suitably protected for further manipulation. Activation of the thiourea with Mukaiyama's reagent allows for the generation of arylguanidines. Mild acid treatment effects deprotection and liberation from the resin to afford guanidines in good yield and high purity.
A mild method for the synthesis of carbamate-protected guanidines using the burgess reagent
Maki, Toshikatsu,Tsuritani, Takayuki,Yasukata, Tatsuro
supporting information, p. 1868 - 1871 (2014/05/06)
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.
