title: Chlorotrimethylsilane activation of acylcyanamides for the synthesis of mono-N-acylguanidines.
abstract: 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.
authors: Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, USA. r.looper@utah.edu
authors: Ryan E
authors: RE
authors: Looper
authors: Travis J
authors: TJ
authors: Haussener
authors: James B C
authors: JB
authors: Mack
mesh_terms: D000588:Amines / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry; D003484:Cyanamide / Q000737:chemistry*; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: D000588:Amines; D000814:Aniline Compounds; D006146:Guanidines; D014297:Trimethylsilyl Compounds; D003484:Cyanamide; C039293:trimethylchlorosilane; C023650:aniline