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
Rearrangements of N-Acyl Isothioureas. Alternate Access to Acylguanidines from Cyanamides / Maestri, Giovanni; M., Larraufie; C., Ollivier; M., Malacria; L., Fensterbank; E., Lacote. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 14:(2012), pp. 5538-5541. [10.1021/ol3026439]
Rearrangements of N-Acyl Isothioureas. Alternate Access to Acylguanidines from Cyanamides
MAESTRI, Giovanni;
2012-01-01
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 materialI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
