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

Giovanni Maestri | Zendy; MarieHélène Larraufie | Zendy; Cyril Ollivier | Zendy; Max Malacrìa | Zendy; Louis Fensterbank | Zendy; Emmanuel Lacôte | Zendy

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

Author(s) -

Giovanni Maestri,

MarieHélène Larraufie,

Cyril Ollivier,

Max Malacrìa,

Louis Fensterbank,

Emmanuel Lacôte

Publication year - 2012

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol3026439

Subject(s) - chemistry , cyanamide , moiety , acyl group , medicinal chemistry , tin , group (periodic table) , stereochemistry , combinatorial chemistry , organic chemistry

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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