- Di-tert-butyl peroxide (DTBP)-mediated synthesis of symmetrical N,N′-disubstituted urea/thiourea motifs from isothiocyanates in water
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ABATRACT: A direct approach to N,N′-disubstituted urea/thiourea from the self-condensation reactions of isothiocyanates in water has been developed. This access tolerated a wide range of functional groups on the aromatic ring, providing a practical and environment-friendly process to N,N′-disubstituted urea/thiourea in moderate to excellent yields from safe and easily available starting materials. A plausible mechanism of the desulfurization self-condensation reaction for urea was also proposed and the role of di-tert-butyl peroxide (DTBP) and copper catalyst in the present strategy was demonstrated with the help of ESI mass spectrometry of intermediate studies.
- Chen, Ling,Dong, Yibo,Wu, Yangjie,Yang, Jinchen,Zhang, Jinli
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supporting information
(2021/12/01)
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- Synthesis method of thiourea
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The invention relates to a synthesis method of thiourea. A method for generating thiourea from amine and carbon disulfide under the action of tertiary amine alkali is a common synthesis method adoptedin the prior art; and when the method is used for preparing the thiourea, a byproduct, namely hydrogen sulfide is generate, and the hydrogen sulfide needs to be fully absorbed by an alkali absorptionsystem and also reacts with the tertiary amine alkali to generate an amine salt, so a large amount of a tertiary amine alkali catalyst needs to be added in the reaction. In order to solve the above problem, the invention provides the synthesis method for thiourea; and according to the synthesis method, a proper amount of an inorganic base is added into a reaction system, so the inorganic base cantimely react with the byproduct hydrogen sulfide to form an inorganic salt without a subsequent alkali absorption system, the usage amount of the catalyst tertiary amine alkali can be greatly reduced, and the subsequent recovery work of a large amount of the tertiary amine alkali is also reduced.
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Paragraph 0020; 0024
(2020/12/08)
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- A facile method for the preparation of carbodiimides from thioureas and (Boc)2O
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A concise method for the preparation of carbodiimides from thioureas using di-tert-butyl dicarbonate [(Boc)2O] as the dehydrosulfurizative reagent has been developed. Using DMAP as the catalyst, a variety of symmetric and asymmetric 1,3-diaryl thioureas were converted into the corresponding carbodiimides efficiently in a short time.
- Wu, He,Sun, Yan-Fang,Zhang, Chen,Miao, Chun-Bao,Yang, Hai-Tao
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supporting information
p. 739 - 742
(2018/01/27)
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- Novel non-peptidic small molecule inhibitors of secreted aspartic protease 2 (SAP2) for the treatment of resistant fungal infections
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Targeting secreted aspartic protease 2 (SAP2), a kind of virulence factor, represents a new strategy for antifungal drug discovery. In this report, the first-generation of small molecule SAP2 inhibitors was rationally designed and optimized using a structure-based approach. In particular, inhibitor 23h was highly potent and selective and showed good antifungal potency for the treatment of resistant Candida albicans infections.
- Dong, Guoqiang,Liu, Yang,Wu, Ying,Tu, Jie,Chen, Shuqiang,Liu, Na,Sheng, Chunquan
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supporting information
p. 13535 - 13538
(2019/01/05)
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- Synthesis of thioureas in ionic liquid medium
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A highly efficient procedure for the synthesis of symmetrical thioureas by means of simple condensation of primary amines and carbon disulfide in 1-butyl-3-methylimidazolium chloride [BMIM][Cl] as a cheap and commercially available ionic liquid is presented. This procedure works for aromatic and aliphatic primary amines and give high to excellent yields of symmetrical thioureas without need for any catalyst or tedious work-up.
- Halimehjani, Azim Ziyaei,Farahbakhsh, Fataneh
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p. 284 - 288
(2013/08/26)
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- A simple and straightforward synthesis of phenyl isothiocyanates, symmetrical and unsymmetrical thioureas under ball milling
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Promoted by KOH under ball milling, anilines were efficiently transformed into isothiocyanates (in presence of 5.0 equiv. CS2) or symmetrical thioureas (in presence of 1.0 equiv. CS2), without using any other harsh or toxic decomposition reagent. Some in situ generated isothiocyanates can directly "click" with other amines to afford unsymmetrical thioureas.
- Zhang, Ze,Wu, Hao-Hao,Tan, Ya-Jun
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p. 16940 - 16944
(2013/09/24)
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- Copper-catalyzed one-pot synthesis of 2-thioxo-2,3-dihydroquinazolin-4(1H)- ones from ortho-bromobenzamides and isothiocyanates
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Copper-catalyzed tandem reaction of ortho-bromobenzamides and isothiocyanates is described, which provides an efficient and practical route for the synthesis of 2-thioxo-2,3-dihydroquinazolin-4(1H)-ones. The optimal condition involved the following parameters: CuI as precatalyst, Cs 2CO3 as base, N,N′-dimethylethane-1,2-diamine as ligand, and toluene as solvent, with reaction temperature at 120 °C.
- Wang, Fei,Zhao, Peng,Xi, Chanjuan
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supporting information; experimental part
p. 231 - 235
(2011/02/28)
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- Thiazolidione derivatives as novel antibiofilm agents: Design, synthesis, biological evaluation, and structure-activity relationships
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Rational designed novel thiazolidiones were synthesized and evaluated for antibiofilm activity. The active derivatives were not only potent inhibitors of Staphylococcus epidermidis biofilm growth but also efficient antibacterial agents. 3f showed 4-fold higher activity (6.25 μM) in the biofilms dispersal assay and significantly higher antibacterial activity (MIC 3.125 μM) in comparison to the 3-(5-((6- (ethoxycarbonyl)-5-(benzo[1,3]dioxol-5-yl)-3-oxo-7- phenyl- thiazolo[3,2-a]pyrimidin-2(5H)-ylidene)methyl)furan-2-yl)benzoic acid (1).
- Pan, Bin,Huang, Renzheng,Zheng, Likang,Chen, Chen,Han, Shiqing,Qu, Di,Zhu, Mingli,Wei, Ping
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scheme or table
p. 819 - 824
(2011/04/16)
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- Design, synthesis, and antibiofilm activity of 2-arylimino-3-aryl-thiazolidine-4-ones
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A series of novel 2-arylimino-3-aryl-thiazolidine-4-ones was designed, synthesized and tested for in vitro antibiofilm activity against Staphylococcus epidermidis. Among them tested, some compounds with carboxylic acid groups showed good antibiofilm activity. The antibiofilm concentration of 1x was 6.25 μM. The structure-activity relationships revealed that incorporation of 2-phenylfuran moiety could greatly enhance antibiofilm activity of thiazolidine-4-one.
- Pan, Bin,Huang, Ren-Zheng,Han, Shi-Qing,Qu, Di,Zhu, Ming-Li,Wei, Ping,Ying, Han-Jie
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scheme or table
p. 2461 - 2464
(2010/07/16)
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- Synthesis and conformational features of sym N,N′,N″- triarylguanidines
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A one pot reaction involving sym N,N′-diarylthiourea and the respective arylamine in the presence of aq. KOH in nitrobenzene at ≥105°C afforded sym N,N′,N″-triarylguanidine in fair to good yield and the products have been characterized. Sym N,N′,N″-tri(4-tolyl)guanidine possesses (7) anti-anti conformation, sym N,N′,N″-tri(2-tolyl) guanidine (8) and sym N,N′,N″-tris(2,4-xylyl)guanidine (11) each possess anti-anti αβα conformation whereas sym N,N′,N″-tris(2-anisyl)guanidine possesses (9) syn-anti αββ conformation as determined by single crystal X-ray diffraction data. The observed conformations appear to result from a subtle balance between steric factor associated with the aryl substituent and multiple electronic factors namely n-π conjugation/negative hyperconjugation and non-covalent interactions in the crystal lattice. Indian Academy of Sciences.
- Gopi, Kanniyappan,Rathi, Brijesh,Thirupathi, Natesan
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experimental part
p. 157 - 167
(2010/11/17)
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- An environmentally benign method for the synthesis of symmetrical N,N′-disubstituted thioureas in a water medium
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An environmentally benign method for the synthesis of symmetrical N,N′-disubstituted thioureas in a water medium using poly(ethylene glycol)-400 (PEG-400) as a catalyst and a microwave as a heating source is described. Diaryl- and dialkyl-thioureas efficiently are synthesized by the reactions of thiourea with a variety of amines. This protocol has advantages of (a) no use of hazardous reagents and volatile organic solvents, (b) a rapid reaction rate, (c) a high yield, and (d) a simple work-up procedure. Copyright Taylor & Francis Inc.
- Li, Zheng,Wang, Zhi-Yuan,Zhao, Yan-Long,Xing, Yu-Lin,Zhu, Wei
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p. 2745 - 2750
(2007/10/03)
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- An efficient acylation/base-catalyzed cyclization of thioureas affords N,N′-disubstituted thiobarbituric acids
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Acylation of 1,3-disubstituted thioureas with methyl malonyl chloride followed by base-catalyzed cyclization leads to the preparation of 1,3-disubstituted-2-thiobarbituric acids in high yield.
- Heath, Perry C.,Huang, Charles Q.,Lowe, Richard F.,McCarthy, James R.,Weigel, Leland O.,Whitten, Jeffery P.
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p. 1607 - 1610
(2007/10/03)
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- A Concise and Convenient Method for the Synthesis of Pure Substituted Thioureas
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Zinc dialkyldithiocarbamates offer excellent substrates for pure thioureas required for the ntifungal and X-ray crystallographic studies.
- Ramadas, K.,Janarthanan, N.
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p. 1101 - 1108
(2007/10/03)
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- Lac sulfur assisted synthesis of symmetrical thioureas
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This work presents a short and attractive method to synthesise a variety of 1,3-disubstituted symmetrical thioureas in high yields.
- Ramadas,Janarthanan,Velmathi
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p. 2255 - 2260
(2007/10/03)
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- Applications of Phase Transfer Catalysis, 26. - Thioureas by Three-Component Reactions of Amines, Carbon Tetrachloride, and Sulfide Ions
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The title reactions proceed exothermically in the presence of a phase transfer catalyst.Thiophosgene is an intermediate in this conversion, and its phase transfer catalytic transformation into carbon disulfide and trithiocarbonate can be demonstrated.Perchloromethanethiol/sodium sulfide and a PT catalyst yield thiophosgene too.Activated vicinal dibromides were debrominated by Na2S/catalyst.
- Broda, Witold,Dehmlow, Eckehard V.
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p. 1839 - 1843
(2007/10/02)
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- A CONVENIENT METHOD FOR THE PREPARATION OF N,N'-DISUBSTITUTED THIOUREAS USING 2-CHLOROPYRIDINIUM SALT, SODIUM TRITHIOCARBONATE AND AMINES
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N,N'-Disubstituted thioureas were prepared in high yields by treating 2-chloropyridinium salt with sodium trithiocarbonate and subsequently adding amines.
- Takikawa, Yuji,Inoue, Noriyuki,Sato, Ryu,Takizawa, Saburo
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p. 641 - 642
(2007/10/02)
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