Synthetic Communications An International Journal for Rapid Communication of Synthetic Organic Chemistry Green Process Development for the Synthesis of Aliphatic Symmetrical N,N′-Disubstituted Thiourea Derivatives in Aqueous Medium (original) (raw)
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Thioureas are of importance in medicinal chemistry due to their biological activities such as antitu-berculosis, anti-HIV, analgesic, anti-inflammatory, antimi-crobial, antiarrhythmic, fungicide, herbicides, rodenticides and as phenoloxidase enzymatic inhibitors. Treatment of primary and secondary amines with thiophosgene is the common method of making symmetrical disubstituted thio-ureas. However, this method is hazardous due to the toxic properties of thiophosgene. Here, we report a green, operationally simple approach for the synthesis of 1, 3-disubsti-tuted thiourea derivatives in moderate to excellent yields of 57–99 %. We use primary amines and CS 2 in water without any catalyst and solar thermal energy. This method is more environmentally benign and energy-saving compared with previously reported methods.
Solid and Solution Phase Organic Syntheses of Oligomeric Thioureas
The Journal of Organic Chemistry, 1996
In order to study supramolecular architectures built from unnatural oligomeric and polymeric structures, one must first have an efficient synthetic strategy to produce them. Oligomers built from thiourea groups should form complex secondary and tertiary structures due to the hydrogenbonding capabilities of the thioureas. Herein, both solution and solid phase synthetic procedures that yield oligomeric thioureas are described. They rely on the coupling of an isothiocyanate with an amine to produce the thiourea linkage. The monomers are derived from simple diamines. Higher yields are achieved using the solid phase method due to the ability to easily monitor the extent of reaction, to use a large excess of reagent, and to perform purification after cleavage from the solid support. A variety of oligomers are given as examples. The procedure is quite general, should be easily extended to complex monomers, and will allow the investigation of intramolecular and intermolecular interactions.
Synthesis of Mono- and N,N - Disubstituted Thioureas and N -Acylthioureas
Synthesis, 2004
1-Benzotriazole-1-carbothioamide (2), prepared from 1cyanobenzotriazole (1) and hydrogen sulfide, reacts with amines to give thioureas 3a-e. Reactions of (benzotriazol-1-yl)carboximidamides 4a-d,f-j and acyl-5a-f,i-k or arylaminocarbonyl-5g,h (benzotriazol-1-yl)carboximidamides with hydrogen sulfide give the corresponding thioureas 3a-d,f-j, and N-acylthioureas 6a-f,i-k or N-carbamoylthioureas 6g,h, respectively.
One-Pot Multicomponent Synthesis of Thiourea Derivatives in Cyclotriphosphazenes Moieties
Journal of Chemistry
In this study, hexasubstituted thiourea was carried out via reaction of isothiocyanato cyclophosphazene intermediates with a series of aromatics amines and amino acids in a one-pot reaction system. The reaction was not as straightforward as typical thiourea synthesis. Six unexpected thiourea derivatives 3a–f were formed in the presence of cyclotriphosphazene moieties in good yields (53–82%). The structures of 3a–f were characterized by elemental analysis and FTIR, 1H, 13C, and 31P NMR spectroscopies. The occurrence of reverse thioureas formation in a one-pot reaction system is discussed. The possible binding interaction of the synthesised thiourea 3a-b in comparison to the predicted phenyl thiourea 5a-b and the targeted 4a with enzyme enoyl ACP reductase (FabI) is also discussed. Molecular docking of the targeted hexasubstituted thiourea 4a is able to give higher binding affinity of −7.5 kcal/mol compared to 5a-b (−5.9 kcal/mol and −6.3 kcal/mol) and thiourea 3a-b (−4.5 kcal/mol and...
Synthesis, characterization, and pharmacological evaluation of thiourea derivatives
Open Chemistry, 2020
Thioureas and their derivatives are organosulfur compounds having applications in numerous fields such as organic synthesis and pharmaceutical industries. Symmetric thiourea derivatives were synthesized by the reaction of various anilines with CS2. The synthesized compounds were characterized using the UV-visible and nuclear magnetic resonance (NMR) spectroscopic techniques. The compounds were screened for in vitro inhibition of α-amylase, α-glucosidase, acetylcholinesterase (AChE), and butyrylcholinesterase (BuChE) enzymes and for their antibacterial and antioxidant potentials. These compounds were fed to Swiss male albino mice to evaluate their toxicological effects and potential to inhibit glucose-6-phosphatase (G6Pase) inhibition. The antibacterial studies revealed that compound 4 was more active against the selected bacterial strains. Compound 1 was more active against 2,2-diphenyl-1-picrylhydrazyl and 2,2’-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) free radicals,...
Synthesis and transformations of 1-[2-(toluene-4-sulfonamido)ethyl]thiourea
hc, 2013
Readily available 2-(toluene-4-sulfonylamino)ethylamine is a convenient starting material for a two-step synthesis of 1-[2-(toluene-4-sulfonamido)ethyl]thiourea (2). Heterocyclization of the thiourea moiety in 2 furnished a thiazole derivative 3 which was further functionalized into substituted thiazoles 4–6. A series of 2-(thiazol-5-yl)-[1,3,4]oxadiazoles 8, 10 and 2-(thiazol-5-yl)-[1,3,4]thiadiazoles 9, 11 were obtained.