29806-60-8

Upstream product

• 622-78-6 Benzyl isothiocyanate 
• 104-94-9 4-methoxy-aniline 
• 2284-20-0 4-Methoxyphenyl isothiocyanate 
• 100-46-9 benzylamine 
• 10349-38-9 p-methoxyphenylisonitrile 
• 56134-95-3 ethyl (4-methoxyphenyl)carbamodithioate 

Downstream Products

• 16763-01-2 N‐benzyl‐6‐methoxybenzo[d]thiazol‐2‐amine 
• 80427-12-9 3-benzyl-2-(4-methoxy-phenylimino)-thiazolidin-4-one 
• 76746-78-6 C₁₆H₁₈N₄OS*2ClH 
• 76746-81-1 N-benzyl-N'-p-methoxyphenylcarbodiimide 
• 76746-61-7 3-amino-4-p-anisyl-5-benzylimino-4,5-dihydro-1,2,4-thiadiazole 
• 76746-71-9 C₁₆H₁₈N₄OS*ClH 
• 88104-42-1 1-Benzyl-3-(4-methoxy-phenyl)-2-methyl-isothiourea 
• 88104-43-2 5-benzylamino-1-p-methoxyphenyl tetrazole 
• 65875-48-1 N-benzyl-N',N'-diethyl-N-(6-methoxy-benzothiazol-2-yl)-ethane-1,2-diamine 
• 1354377-88-0 tert-butyl 2-[1-[3-benzyl-2-[(4-methoxyphenyl)imino]-4-oxo-1,3-thiazolidin-5-ylidene]ethyl]hydrazinecarboxylate 
• 126679-87-6 N-benzyl-N’-(4-methoxyphenyl)urea 

Relevant academic research and scientific papers

Chromatography-Free Multicomponent Synthesis of Thioureas Enabled by Aqueous Solution of Elemental Sulfur

The development of a new three-component chromatography-free reaction of isocyanides, amines and elemental sulfur allowed us the straightforward synthesis of thioureas in water. Considering a large pool of organic and inorganic bases, we first optimized the preparation of aqueous polysulfide solution from elemental sulfur. Using polysulfide solution, we were able to omit the otherwise mandatory chromatography, and to isolate the crystalline products directly from the reaction mixture by a simple filtration, retaining the sulfur in the solution phase. A wide range of thioureas synthesized in this way confirmed the reasonable substrate and functional group tolerance of our protocol.

Preparation method of thiourea alkylation derivative

The invention discloses a preparation method of a thiourea alkylation derivative, which comprises the following steps: stirring an aldehyde, N-arylthiourea, trichlorosilane and Lewis base in an organic solvent at a range of -10 DEG C to room temperature for reaction, and carrying out after-treatment to obtain the thiourea alkylation derivative, wherein the molar ratio of the aldehyde to the N-arylthiourea is 1:2 to 2:1, the molar ratio of the aldehyde to the Lewis base is 1:(0.01-0.20), the molar ratio of the aldehyde to trichlorosilane is 1:(1-2), R1 is a C1-C5 saturated alkyl group, or an unsubstituted or substituted aromatic ring, and R2 is H, an electron withdrawing substituent or an electron donating substituent. According to the method, trichlorosilane is catalyzed by the micromolecular Lewis base, reductive alkylation of thiourea is realized, synthesis can be realized by a one-pot method, and the method is simple to operate, short in reaction time, low in substrate toxicity, lowin cost, easy to obtain, mild in reaction condition and high in safety.

Synthesis and molecular docking of N,N′-disubstituted thiourea derivatives as novel aromatase inhibitors

A three series of thioureas, monothiourea type I (4a–g), 1,4-bisthiourea type II (5a–h) and 1,3-bisthiourea type III (6a–h) were synthesized. Their aromatase inhibitory activities have been evaluated. Interestingly, eight thiourea derivatives (4e, 5f–h, 6d, 6f–h) exhibited the aromatase inhibitory activities with IC50 range of 0.6–10.2 μM. The meta-bisthiourea bearing 4-NO2 group (6f) and 3,5-diCF3 groups (6h) were shown to be the most potent compounds with sub-micromolar IC50 values of 0.8 and 0.6 μM, respectively. Molecular docking also revealed that one of the thiourea moieties of these two compounds could mimic steroidal backbone of the natural androstenedione (ASD) via hydrophobic interactions with enzyme residues (Val370, Leu477, Thr310, and Phe221 for 6f, Val370, Leu477, Ser478, and Ile133 for 6h). This is the first time that the bisthioureas have been reported for their potential to be developed as aromatase inhibitors, in which the 4-NO2 and 3,5-diCF3 analogs have been highlighted as promising candidates.

A model for a solvent-free synthetic organic research laboratory: Click-mechanosynthesis and structural characterization of thioureas without bulk solvents

The mechanochemical click coupling of isothiocyanates and amines has been used as a model reaction to demonstrate that the concept of a solvent-free research laboratory, which eliminates the use of bulk solvents for either chemical synthesis or structural characterization, is applicable to the synthesis of small organic molecules. Whereas the click coupling is achieved in high yields by simple manual grinding of reactants, the use of an electrical, digitally controllable laboratory mill provides a rapid, quantitative and general route to symmetrical and non-symmetrical aromatic or aromatic-aliphatic thioureas. The enhanced efficiency of electrical ball milling techniques, neat grinding or liquid-assisted grinding, over manual mortar-and-pestle synthesis is demonstrated in the synthesis of 49 different thiourea derivatives. Comparison of powder X-ray diffraction data of mechanochemical products with structural information found in the Cambridge Structural Database (CSD), or obtained herein through single crystal X-ray diffraction, indicates that the mechanochemically obtained thiourea derivatives are pure in a chemical sense, but can also demonstrate purity in a supramolecular sense, i.e. in all structurally explored cases the product consisted of a single polymorph. As an extension of our previous work on solvent-free synthesis of coordination polymers, it is now demonstrated that such polymorphic and chemical purity of selected thiourea derivatives, the latter being evidenced through quantitative reaction yields, can enable the direct solvent-free structural characterization of mechanochemical products through powder X-ray diffraction aided by solid-state NMR spectroscopy.

Powerful approach to heterocyclic skeletal diversity by sequential three-component reaction of amines, isothiocyanates, and 1,2-diaza-1,3-dienes

By highly efficient, one-pot, three-component reactions, combining one set of 1,2-diaza-1,3-dienes (DDs), primary amines, and isothiocyanates in a different sequential order of addition, heterocyclic skeletal diversity can be achieved. The key feature dis

A simple and green procedure for the synthesis of N-benzylthioureas

A simple and efficient reaction protocol for the synthesis of N-benzylthioureas is described from benzylisothiocyanate (BITC: 94% pure/GC-MS), isolated from crushed papaya seeds.

Use of molecular oxygen as a reoxidant in the synthesis of 2-substituted benzothiazoles via palladium-catalyzed C-H functionalization/intramolecular C-S bond formation

Molecular oxygen (O2) was successfully employed as a reoxidant in cyclizations of thiobenzanilides 1a-s through a palladium-catalyzed C-H functionalization/intramolecular C-S bond formation process, leading to an efficient, green method for the synthesis of 2-arylbenzothiazoles 2a-s. Addition of cesium fluoride (CsF) greatly enhanced the reactions, which produced variously substituted 2-arylbenzothiazoles with good functional group tolerance. Thioureas 4a-j were also found to be suitable substrates for the cyclization process using a palladium/O2 catalyst system, thus generating 2-aminobenzothiazoles 5a-j. One-pot syntheses of 2-aminobenzothiazoles 5a-j from aryl isothiocyanates 6 and amines 7 were also successful.

Highly efficient and catalyst-free synthesis of unsymmetrical thioureas under solvent-free conditions

A highly efficient and simple synthesis of unsymmetrical thioureas is reported based on the reaction of readily synthesized dithiocarbamates with amines, without using any catalyst under solvent-free conditions. The short reaction time, high yields, and s

Synthesis of 3(S)-acylamino-1-[(phenyl)-(1H-tetrazol-5-yL)amino]-2-azetidinones

1-Phenyl-1-(1-benzyl-1H-tetrazol-5-yl)hydrazine has been synthesized from N1-benzyloxycarbonyl-N2-phenylhydrazide and benzyl isothiocyanate. Coupling with N-(benzyloxycarbonyl)-L-serine 3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-yl ester