Chlorotrimethylsilane Activation of Acylcyanamides for the Synthesis of Mono-N-acylguanidines
Ryan E. Looper*, Travis J. Haussener and James B. C. Mack
*Department of Chemistry, University of Utah, 315 South 1400
East, Salt lake City, Utah 84112, United States,
Email: r.looper
utah.edu
R. E. Looper, T. J. Haussener, J. B. C. Mack, J. Org. Chem., 2011, 76, 6967-6971.
DOI: 10.1021/jo201264j
Abstract
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 room temperature. Hindered amines and anilines are also competent nucleophiles but require extended reaction times.
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ID: J42-Y2011-2340
