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. 2011 Aug 19;76(16):6967-71.
doi: 10.1021/jo201264j. Epub 2011 Jul 19.

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

Ryan E Looper  1 , Travis J Haussener, James B C Mack
Affiliations

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

Ryan E Looper et al. J Org Chem. .

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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Figures

Figure 1
Figure 1
Common guanylation reagents.
Scheme 1
Scheme 1. Preparation of benzyloxycarbonylcyanamide potassium salt
Scheme 2
Scheme 2. Guanidine deprotection
See this image and copyright information in PMC

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