Journal of Organic Chemistry 2011-08-19

Chlorotrimethylsilane activation of acylcyanamides for the synthesis of mono-N-acylguanidines.

Ryan E Looper, Travis J Haussener, James B C Mack

Index: J. Org. Chem. 76(16) , 6967-71, (2011)

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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.