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Article Dans Une Revue Organic Letters Année : 2012

Rearrangements of N-Acyl Isothioureas. Alternate Access to Acylguanidines from Cyanamides

Résumé

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 Hunig'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.

Domaines

Chimie organique
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Dates et versions

hal-01397630 , version 1 (05-05-2020)

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Giovanni Maestri, Marie-Hélène Larraufie, Cyril Ollivier, Max Malacria, Louis Fensterbank, et al.. Rearrangements of N-Acyl Isothioureas. Alternate Access to Acylguanidines from Cyanamides. Organic Letters, 2012, 14 (21), pp.5538-5541. ⟨10.1021/ol3026439⟩. ⟨hal-01397630⟩
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