22102-72-3Relevant academic research and scientific papers
A mild method for the synthesis of carbamate-protected guanidines using the burgess reagent
Maki, Toshikatsu,Tsuritani, Takayuki,Yasukata, Tatsuro
, 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.
Chlorotrimethylsilane activation of acylcyanamides for the synthesis of mono-N-acylguanidines
Looper, Ryan E.,Haussener, Travis J.,MacK, James B. C.
, p. 6967 - 6971 (2011/10/04)
A simple and efficient one-pot method for the synthesis of monoprotected guanidines is presented. Treatment of an acylcyanamide with chlorotrimethylsilane generates a reactive N-silylcarbodiimide capable of guanylating a variety of amines. Typically the reaction is complete in 15 min for primary and secondary aliphatic amines at rt. Hindered amines and anilines are also competent nucleophiles but require extended reaction times.
