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Mechanochemical synthesis of thioureas, ureas and guanidines

Štrukil, Vjekoslav (2017) Mechanochemical synthesis of thioureas, ureas and guanidines. Beilstein journal of organic chemistry, 13 . pp. 1828-1849. ISSN 1860-5397

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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.

Item Type: Article
Uncontrolled Keywords: guanidines ; mechanochemistry ; solid state synthesis ; thioureas ; ureas
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Depositing User: Vjekoslav Štrukil
Date Deposited: 19 Jan 2018 09:16
DOI: 10.3762/bjoc.13.178

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