Categories: C-N Bond Formation >
Synthesis of thioureas
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Recent Literature
A simple condensation between amines and carbon disulfide in aqueous medium
allows an efficient synthesis of symmetrical and unsymmetrical substituted
thiourea derivatives. This protocol works smoothly with aliphatic primary amines
to afford various di- and trisubstituted thiourea derivatives.
M. R. Maddani, K. R. Prabhu, J. Org. Chem., 2010,
75, 2327-2332.
A completely atom-economic reaction of isocyanides with aliphatic amines in the
presence of elemental sulfur proceeds efficiently at (nearly) ambient
temperature to produce thioureas in excellent yields.
T. B. Nguyen, L. Ermolenko, A. Al-Mourabit, Synthesis, 2014, 46,
3172-3179.
An "on-water" reaction of (thio)isocyanates with amines enables a facile,
sustainable, and chemoselective synthesis of unsymmetrical (thio)ureas. The
physical nature and solubility of reagents in water are responsible for the
observed reaction rate and selectivity. The process offers simple product
isolation through filtration and the recycling of the water effluent and avoids
the use of toxic VOCs.
A. D. Karche, P. Kamalakannan, R. Powar, G. G. Shenoy, K. J. Padiya,
Org. Process Res. Dev..,
2022, 26, 3141-3152.
The combination of sulfur and chloroform enables an efficient and practical
synthesis of a thiocarbonyl surrogate. Various thiocarbamides and
oxazolidinethiones have been synthesized, including chiral thiourea catalysts
and chiral oxazolidinethione auxiliaries with high selectivity.
W. Tan, J. Wei, X. Jiang, Org. Lett.,
2017, 19, 2166-2169.
Carbamoyl isothiocyanates are ideal starting materials for the synthesis of
multisubstituted guanidines. The nature of these carbamoyl thioureas permits
creation of disubstituted and trisubstituted guanidines, as well as aromatic
guanidines.
B. R. Linton, A. J. Carr, B. P. Orner, A. D. Hamilton, J. Org. Chem., 2000,
65, 1566-1568.
Various thioureas derived from primary amines and carbamoyl-protected
isothiocyanates react with the Burgess reagent to give the corresponding
guanidines via either a stepwise or one-pot procedure. A selective deprotection
of the N,N′-diprotected guanidines affords N-monoprotected
guanidines.
T. Maki, T. Tsuritani, T. Yasukata, Org. Lett., 2014,
16, 1868-1871.
Stable and readily available N,N'-di-Boc-substituted thiourea can be used
as a mild thioacylating agent when activated with trifluoroacetic acid anhydride.
Through thioacylation of nucleophiles, such as amines, alcohols, thiols, sodium
benzenethiolate, and sodium malonates, a series of thiocarbonyl compounds were
prepared with good chemical selectivity and functional group tolerance.
B.-L. Yin, Z.-G. Liu, J.-C. Zhang, Z.-R. Li, Synthesis, 2010,
991-999.