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2017 ; 13
(ä): 1828-1849
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Mechanochemical synthesis of thioureas, ureas and guanidines
#MMPMID28904627
?trukil V
Beilstein J Org Chem
2017[]; 13
(ä): 1828-1849
PMID28904627
show ga
In this review, the recent progress in the synthesis of ureas, thioureas and
guanidines by solid-state mechanochemical ball milling is highlighted. While the
literature is abundant on their preparation in conventional solution environment,
it was not until the advent of solvent-free manual grinding using a mortar and
pestle and automated ball milling that new synthetic opportunities have opened.
The mechanochemical approach not only has enabled the quantitative synthesis of
(thio)ureas and guanidines without using bulk solvents and the generation of
byproducts, but it has also been established as a means to develop "click-type"
chemistry for these classes of compounds and the concept of small molecule
desymmetrization. Moreover, mechanochemistry has been demonstrated as an
effective tool in reaction discovery, with emphasis on the reactivity differences
in solution and in the solid state. These three classes of organic compounds
share some structural features which are reflected in their physical and chemical
properties, important for application as organocatalysts and sensors. On the
other hand, the specific and unique nature of each of these functionalities
render (thio)ureas and guanidines as the key constituents of pharmaceuticals and
other biologically active compounds.