93870-87-2Relevant academic research and scientific papers
Rearrangements of N-acyl isothioureas. alternate access to acylguanidines from cyanamides
Maestri, Giovanni,Larraufie, Marie-Helene,Ollivier, Cyril,Malacria, Max,Fensterbank, Louis,Lacote, Emmanuel
supporting information, p. 5538 - 5541,4 (2020/10/15)
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 Huenig'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.
