Chlorotrimethylsilane activation of acylcyanamides for the synthesis of mono-N-acylguanidines |
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Authors: | Looper Ryan E Haussener Travis J Mack James B C |
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Institution: | Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, USA. r.looper@utah.edu |
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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. |
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