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. 2012 Nov 2;14(21):5538-41.
doi: 10.1021/ol3026439. Epub 2012 Oct 23.

Rearrangements of N-acyl isothioureas. Alternate access to acylguanidines from cyanamides

Giovanni Maestri  1 , Marie-Hélène Larraufie, Cyril Ollivier, Max Malacria, Louis Fensterbank, Emmanuel Lacôte
Affiliations

Rearrangements of N-acyl isothioureas. Alternate access to acylguanidines from cyanamides

Giovanni Maestri et al. Org Lett. .

Abstract

We report a tin-free one-pot radical approach to the synthesis of N-acyl isothioureas and acylguanidines from N-acyl cyanamides. Photoactivated reduction of aromatic disulfides in the presence of Hünig's base results in hydrothiolation of the cyanamide moiety, followed by spontaneous 1,3-migration of the acyl group. Onward reaction of the isothioureas obtained with amines led to the corresponding N-acylguanidines, where the acyl group is attached to the nitrogen atom formerly at the cyano-end of the starting material.

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