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Synlett 2016; 27(18): 2591-2596
DOI: 10.1055/s-0035-1562478
DOI: 10.1055/s-0035-1562478
letter
Facile Guanidine Formation under Mild Acidic Conditions
Further Information
Publication History
Received: 31 May 2016
Accepted after revision: 23 June 2016
Publication Date:
01 August 2016 (online)
![](https://www.thieme-connect.de/media/synlett/201618/lookinside/thumbnails/st-2016-u0372-l_10-1055_s-0035-1562478-1.jpg)
Abstract
An efficient method for converting isothioureas into guanidines was developed. The use of amine salts of bis(trifluoromethanesulfonyl)imide as a nitrogen source was found to induce an efficient conversion under weak acidic conditions at 50 °C. The conversion was applicable to the various amines and carbamate-protected thioureas, and various carbamate-protected cyclic guanidines were obtained in high yields. In particular, ammonium bis(trifluoromethanesulfonyl)imide salt is a useful N1 source with which to construct monoprotected cyclic guanidines.
Key words
guanidinylation - cyclic guanidine - isothiourea - bis(trifluoromethansulfonyl)imide - ammonium bis(trifluoromethansulfonyl)imidateSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562478.
- Supporting Information
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For recent reviews, see:
For patents, see:
In the case of unprotected acyclic isothioureas, there have been several examples of guanidinylation reaction under mild acidic conditions. For selected recent examples, see:
For recent application of nitrobenzyl group to total synthesis, see: