- A New Synthesis of Aliphatic Isothiocyanates from Primary Amines, Convenient for In Situ Use
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Primary aliphatic amines react with carbon disulfide in the presence of BOP (benzotriazole-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate) 1, giving the corresponding isothiocyanates in good to high yields and high purity; a number of isothiocyanates are synthesized and isolated or generated in situ and treated with a nucleophile.
- Boas, Ulrik,Jakobsen, Mogens Havsteen
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- Identification of organophosphorus simulants for the development of next-generation detection technologies
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Organophosphorus (OP) chemical warfare agents (CWAs) represent an ongoing threat but the understandable widespread prohibition of their use places limitations on the development of technologies to counter the effects of any OP CWA release. Herein, we describe new, accessible methods for the identification of appropriate molecular simulants to mimic the hydrogen bond accepting capacity of the PO moiety, common to every member of this class of CWAs. Using the predictive methodologies developed herein, we have identified OP CWA hydrogen bond acceptor simulants for soman and sarin. It is hoped that the effective use of these physical property specific simulants will aid future countermeasure developments.
- Ellaby, Rebecca J.,Clark, Ewan R.,Allen, Nyasha,Taylor, Faith R.,Ng, Kendrick K. L.,Dimitrovski, Milan,Chu, Dominique F.,Mulvihill, Daniel P.,Hiscock, Jennifer R.
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p. 2008 - 2014
(2021/03/16)
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- Gram Scalable Method to Synthesize Biscarbodiimides and Asymmetric Monocarbodiimides: A Platform to Access an Array of Phosphaguanidines, Amidines, and Guanidines
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A mild, broadly functional group tolerant methodology has been developed to access a variety of mono- and bis-carbodiimides in good yield and high purity on multigram scale. Direct addition into these versatile motifs facilitated the rapid synthesis of a library of novel amidinines, guanidines, and phosphaguandines.
- Bailey, Brad,Camelio, Andrew M.,Davis, Anna,Krasovskiy, Arkady
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- Direct, Microwave-Assisted Synthesis of Isothiocyanates
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A microwave-assisted desulfuration of readily available dithiocarbamates, formed in situ from primary amines, leading to target isothiocyanates has been developed. This efficient protocol provides a rapid, environmentally benign route to aliphatic and aromatic isothiocyanates.
- Janczewski, ?ukasz,Gajda, Anna,Gajda, Tadeusz
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p. 2528 - 2532
(2019/04/03)
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- Synthesis Of di- and tri-substituted thiourea derivatives in water using choline chloride–urea catalyst
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In this work, di- and tri-substituted thiourea derivatives have been synthesized via a one-pot, three-component reaction from carbon disulfide and aliphatic or aromatic amines using choline chloride-urea deep eutectic solvent as a catalyst in water. Both cyclic and acyclic thiourea derivatives with two or three substituents were synthesized successfully. The reactions were done at 25–100°C, using 5–20 mol% catalyst, in 3–5 h and the GC-Mass yields were between 60% and 95%. All products were characterized using FT-IR, 1H-NMR, 13C-NMR, GC-MS and melting point analyses. The results showed that both water and the DES have important effects on the yield and the rate of this reaction and both of them are necessary to obtain higher yields in less time. The extra experiment, which was designed to study the mechanism of the reaction, showed that an isothiocyanate intermediate was formed in the reaction. Finally, the results showed that by the increase of the amine's nucleophilicity, the reaction occurs faster and gives higher yield.
- Tavakol, Hossein,Mahmoudi, Amir,Ranjbari, Mohammad-Amin
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p. 113 - 123
(2018/10/24)
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- Pos [...] 4 group metal olefin polymerization catalyst
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Embodiments are directed to phosphaguanidine metal complexes of formula I and using those complexes in α-olefin polymerization systems.
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Paragraph 0372
(2019/08/27)
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- Novel self-condensation of ammonium dithiocarbamates leading to symmetrical substituted thioureas
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For the first time, the formation of symmetrical substituted thiourea analogues generated by the selfcondensation of trialkylammoniumdithiocarbamates is reported. The reactions occurred under mild conditions. The method allows the use of amines possessing a weak nucleophilic feature in good yields. The highlight of the study is a novel self-condensation mechanism based on dithiocarbamates as a basic compound in organic chemistry.
- üng?ren, ?evket Hakan,S?r?a, Fatih
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supporting information
p. 28 - 33
(2016/12/24)
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- Rapid and highly efficient synthesis of thioureas in biocompatible basic choline hydroxide
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A straightforward and convenient synthesis of symmetrical thiourea derivatives by the reaction of primary amines and carbon disulfide in biocompatible basic choline hydroxide is presented. A variety of biologically important thiourea derivatives can be obtained in good to excellent yields without a tedious work-up under mild reaction conditions. A series of primary aliphatic and aromatic amines with different substituted functional groups have been converted to thiourea derivatives under milder reaction conditions and short reaction times.
- Azizi, Najmedin,Farhadi, Elham
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p. 548 - 554
(2017/09/27)
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- Green process development for the synthesis of aliphatic symmetrical N,N'-disubstituted thiourea derivatives in aqueous medium
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A highly efficient green process for the synthesis of N,N'-disubstituted aliphatic thiourea derivatives using primary aliphatic amines and carbon disulfide in aqueous medium at room temperature via a nonisothiocyanate route is described. This protocol illustrates the rapid preparation of N,N'-disubstituted aliphatic thiourea derivatives in excellent yields with some advantages such as no catalyst and simple workup without any side product formation. Moreover the new route is concise, chromatography-free, and adaptable to pilot-scale preparation.
- Jangale, Asha D.,Kumavat, Priyanka P.,Wagh, Yogesh B.,Tayade, Yogesh A.,Mahulikar, Pramod P.,Dalal, Dipak S.
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p. 236 - 244
(2015/10/29)
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- Green Process Development for the Synthesis of Aliphatic Symmetrical N,N ′-Disubstituted Thiourea Derivatives in Aqueous Medium
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A highly efficient green process for the synthesis of N,N′-disubstituted aliphatic thiourea derivatives using primary aliphatic amines and carbon disulfide in an aqueous medium at room temperature via a nonisothiocyanate route is described. This protocol illustrates the rapid preparation of N,N′-disubstituted aliphatic thiourea derivatives in excellent yields with some advantages such as no catalyst and simple workup without any side product formation. Moreover, the new route is concise, does not require chromatography, and is adaptable to pilot-scale preparation. GRAPHICAL ABSTRACT.
- Jangale, Asha D.,Kumavat, Priyanka P.,Wagh, Yogesh B.,Tayade, Yogesh A.,Mahulikar, Pramod P.,Dalal, Dipak S.
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supporting information
p. 376 - 385
(2015/10/29)
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- The use of κ-carrageenan/Fe3O4 nanocomposite as a nanomagnetic catalyst for clean synthesis of rhodanines
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In this work, magnetically separable Fe3O4 nanoparticles were synthesized in the presence of natural κ-carrageenan (KCAR) biopolymer to provide Fe3O4@KCAR. FT-IR analysis, scanning electron microscopy (SEM), X-ray diffraction, VSM analysis, and SEM-EDAX were incorporated for the characterization of Fe3O4@KCAR nanocomposite. And then, the first catalytic report of Fe3O4@KCAR with no post-modification was achieved by studying its catalytic activity in the multicomponent reaction of rhodanine synthesis. Based on this study, Fe3O4@KCAR was an efficient, magnetically separable and recyclable, water-dispersible and green catalyst with natural source. This catalyst also showed 9-run recyclability with no significant yield decrease.
- Rostamnia, Sadegh,Zeynizadeh, Behzad,Doustkhah, Esmail,Baghban, Ali,Aghbash, Khadijeh Ojaghi
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- Application of "hydrogen bonding interaction" in new drug development: Design, synthesis, antiviral activity, and sars of thiourea derivatives
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A series of simple thiourea derivatives were designed based on the structure of natural product harmine and lead compound and synthesized from amines in one step. The antiviral activity of these thiourea derivatives was evaluated. Most of them exhibited significantly higher anti-TMV activity than commercial plant virucides ribavirin, harmine, and lead compound. The hydrogen bond was found to be important but not the more the better. The optimal compound (R,R)-20 showed the best anti-TMV activity in vitro and in vivo (in vitro activity, 75%/500 a??g/mL and 39%/100 a??g/mL; inactivation activity, 71%/500 a??g/mL and 35%/100 a??g/mL; curative activity, 73%/500 a??g/mL and 37%/100 a??g/mL; protection activity, 69%/500 a??g/mL and 33%/100 a??g/mL), which is significantly higher than that of Ningnanmycin. The systematic study provides strong evidence that these simple thiourea derivatives could become potential TMV inhibitors.
- Lu, Aidang,Wang, Ziwen,Zhou, Zhenghong,Chen, Jianxin,Wang, Qingmin
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p. 1378 - 1384
(2015/03/05)
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- A highly efficient one-pot method for the synthesis of thioureas and 2-imino-4-thiazolidinones under microwave conditions
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A one-pot synthesis of symmetrical and unsymmetrical substituted thioureas and 2-imino-4-thiazolidinones from simple starting materials under microwave irradiation and solventless conditions without base additives is presented. Various di- and trisubstituted thioureas are obtained in good yields in a few minutes. The sequential, three-component, one-pot synthesis of 2-imino-4-thiazolidinone derivatives is also studied, with satisfactory results obtained.
- Chau, Chi-Min,Chuan, Tzu-Jung,Liu, Kuan-Miao
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p. 1276 - 1282
(2014/01/06)
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- Convenient synthesis of 5-arylidene-2-imino-4-thiazolidinone derivatives using microwave irradiation
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A concise approach for the preparation of 5-arylidene-2-imino-4- thiazolidinone derivatives is described. Structurally diverse amines, isothiocyanates, aldehydes, and chloroacetyl chloride were combined under microwave irradiation to afford new 5-arylidene-2-imino-4-thiazolidinone derivatives. The one-pot synthesis involves the in situ formation of a thiourea followed by reaction with chloroacetyl chloride and an aldehyde to generate the target compounds. Georg Thieme Verlag Stuttgart New York.
- Sarkis, Manal,Tran, Diem-Ngan,Dasso Lang, Maria Chiara,Garbay, Christiane,Braud, Emmanuelle
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p. 1257 - 1262
(2014/06/10)
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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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- One-pot synthesis of S-alkyl dithiocarbamates via the reaction of N-tosylhydrazones, carbon disulfide and amines
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A new, convenient and efficient transition metal-free synthesis of S-alkyl dithiocarbamates through one-pot reaction of N-tosylhydrazones, carbon disulfide and amines is reported. Tosylhydrazones derived from various aromatic and aliphatic ketones or aldehydes were tested and gave dithiocarbamates in good to excellent yields. The tosylhydrazones can be generated in situ without isolation, which provides a simpler one-pot method to synthesize dithiocarbamates via the reaction of carbonyl compounds, carbon disulfide and amines in the presence of 4-methylbenzenesulfonohydrazide.
- Sha, Qiang,Wei, Yun-Yang
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supporting information
p. 5615 - 5620
(2013/09/12)
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- Synthesis and characterisation of [(en)2Co]3+ complexes coordinated by substituted thiourea ligands
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Substituted thiourea ligands bind in a bidentate manner forming a four-membered ring through the sulfur atom and a deprotonated thiourea nitrogen atom when reacted with [(en)2Co(OSO2CF3)2]+ in tetramethylene sulfone. Reaction of unsymmetrical ligands results in the formation of coordination isomers, some of which can be separated by column chromatography using Sephadex SPC-25. Coordination isomers are easily distinguishable based on visible and 1H NMR spectroscopy . Twelve para-substituted and one meta-substituted ligands were studied: N,N′-dibenzylthiourea (1a); N-(R)phenyl-N′-benzylthiourea R≤H (2a), NO2 (2b), CH3 (2c); N-(R)phenyl-N′-(R′)phenylthiourea R, R′: H, H (3a), H, CH3 (3b), OCH3, NO2 (3c), CH3, NO2 (3d); N-methyl-N′-(R)phenylthiourea R≤H (4a), CH3 (4b), OCH3 (4c), NO2 (4d), 3-CH3 (4e). The solid state structure (X-ray) of one isomer of Co-4a as its perchlorate salt confirms the coordination mode suggested by 1H NMR spectroscopy and shows that the Co-N bond trans to the coordinated thiourea sulfur induces a structural trans effect of 0.019A.
- Roecker, Lee,Aiyegbo, Mohammed,Al-Haddad, Aladdin,Fletcher, Emily,Kc, Ravi,Hurst, Jason,Lane, Timothy,Larsen, Ryan,Noinaj, Nicholas,Teh, Say Lee,Wade, Samuel K.,Parkin, Sean
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p. 944 - 951
(2013/09/12)
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- A simple route for the synthesis of symmetrical thiourea derivatives and amidinium cations by reaction between isocyanides, amines and carbon disulfide
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Reaction between primary amines and CS2 promoted by alkyl isocyanides in ethanol as solvent provides a simple and efficient route for the synthesis of symmetrical thiourea derivatives. The reaction of secondary amines with carbon disulfide and alkyl isocyanides afforded new amidinium cations in good yields.
- Anary-Abbasinejad, Mohammad,Karimi, Nadia,Mehrabi, Hossein,Ranjbar-Karimi, Reza
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p. 653 - 659
(2013/02/22)
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- A bioinspired look at the glucosinolate metabolic pathway. Structural insights into the reaction of benzyl isothiocyanate and d-glucosamine
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Through a well-established enzymatic transformation glucosinolates release reactive isothiocyanates that can undergo further metabolic pathways affording a plethora of reactive metabolites. This study explores in detail the reaction of benzyl isothiocyanate, which possesses antitumor activity as alkylating agent, with d-glucosamine, commonly employed in oral treatments against osteoarthritis and inflammation. Structures of the resulting products and their evolution have been assessed and compared with those involving d-glucose, reported previously. Chemical results suggest that clinical treatments with d-glucosamine could reduce the beneficial effects associated with diets based on glucosinolate-rich foods.
- Silvero, Guadalupe,ávalos, Martín,Babiano, Reyes,Cintas, Pedro,Jiménez, José L.,Palacios, Juan C.
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experimental part
p. 7811 - 7820
(2011/10/12)
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- A simple and green procedure for the synthesis of N-benzylthioureas
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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.
- De Sequeira Aguiar, Lucia C.,Viana, Gil M.,Dos Santos Romualdo, Marcus V.,Costa, Marcio V.,Bonato, Bruno S.
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experimental part
p. 540 - 544
(2012/06/01)
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- Novel thiofomylation of primary and secondary amines using N-aryl-1,2,3,4,5,7-pentathiazocanes
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Heating of N-aryl-1,2,3,4,5,7-pentathiazocanes 1 in the presence of primary and secondary amines afforded N-Alkyl or N,N-dialkylthioformamides 5, and similar heating of 1 in the absence of amines afforded an inseparable mixture of acyclic polysulfides 4 bearing a thioformanilide moiety on each terminal. Bisthioformanilides 4 were also converted into 5 by treating with these amines, and the thioformylation was assumed to proceed through a pathway involving the ring fission of 1 and the subsequent nucleophilic attack of these amines onto the thioformyl group of 4. Copyright Taylor & Francis Group.
- Shimada, Kazuaki,Shibuya, Hiroki,Makino, Kenshiro,Otsuka, Tatsuya,Onuma, Yuki,Aoyagi, Shigenobu,Takikawa, Yuji
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scheme or table
p. 1077 - 1089
(2010/09/04)
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- Effect of successive increase in alcohol chains on reaction with isocyanates and isothiocyanates
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The reaction of isocyanates and isothiocyanates with long-chain alcohols, e.g. n-hexanol, n-heptanol and n-octanol, exclusively gave N-aryl-O-alkyl carbamates, while N-aryl-O-alkyl carbamates were formed along with symmetrical 1,3-disubstituted ureas and thioureas when the same reactions were carried out with small-chain alcohols at room temperature without using any solvent.
- Perveen, Shahnaz,Yasmin, Arfa,Khan, Khalid Mohammed
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experimental part
p. 18 - 23
(2010/04/23)
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- A concise synthesis of substituted thiourea derivatives in aqueous medium
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(Figure Presented) An efficient method for the synthesis of symmetrical and unsymmetrical substituted thiourea derivatives by means of simple condensation between available building blocks such as amines and carbon disulfide in aqueous medium is presented. This protocol works smoothly with aliphatic primary amines to afford various di- and trisubstituted thiourea derivatives. The present method is also useful in synthesizing various substituted 2-mercapto imidazole heterocycles. This method proceeds through a xanthate (amino dithiol deivative) intermediate, unlike isothiocyanate as in an earlier known method.
- Maddani, Mahagundappa R.,Prabhu, Kandikere R.
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supporting information; experimental part
p. 2327 - 2332
(2010/07/02)
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- Efficient method of synthesis of N,N′-disubstituted ureas/thioureas by a Zinc chloride catalyzed thermal reaction
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Symmetrically N,N'-disubstituted ureas/thioureas were synthesized by heating amines or phenyl hydrazine and urea/thiourea on a preheated hot plate at 80-85C under solvent-free conditions in the presence of a catalytic amount of ZnCl2 as a catalyst. The protocol has the advantages of not using toxic phosgene and other hazardous substrates or organic solvents. Increased reaction rate, good yield, and a simple workup procedure are involved.
- Pasha,Madhusudana Reddy
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experimental part
p. 2928 - 2934
(2009/12/03)
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- Carbon tetrabromide promoted reaction of amines with carbon disulfide: Facile and efficient synthesis of thioureas and thiuram disulfides
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A novel carbon tetrabromide promoted one-pot reaction of amines and carbon disulfide under mild conditions has been developed, which provides a straightforward and efficient access to thioureas and thiuram disufides, depending on the nature of the amines employed. The promotion effect is explained as the transient formation of a sulfenyl bromide intermediate from dithiocarbamate and carbon tetrabromide during the reaction. Georg Thieme Verlag Stuttgart · New York.
- Liang, Fushun,Tan, Jing,Piao, Chengri,Liu, Qun
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experimental part
p. 3579 - 3584
(2009/07/04)
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- 1-(Methyldithiocarbonyl)imidazole as thiocarbonyl transfer reagent: A facile one-pot three-component synthesis of 3,5- and 1,3,5-substituted-2- thiohydantoins
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An efficient three-component one-pot synthesis of 3,5-and 1,3,5-substituted 2-thiohydantoins employing easily accessible amino acid esters, primary amines and 1-(methyldithiocarbonyl)imidazole as thiocarbonyl transfer reagent has been reported. Georg Thieme Verlag Stuttgart.
- Sundaram,Venkatesh,Ila,Junjappa
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p. 251 - 254
(2007/10/03)
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- Synthesis and anion-selective complexation of homobenzylic tripodal thiourea derivatives
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Cryptand- and tripod-type thiourea derivatives 4b and 5a-d, which have binding functionalities at the homobenzylic positions, were synthesized as possible neutral receptors toward anions with an expectation that the three binding sites work cooperatively to bind an anion selectively. 1H NMR spectroscopic monitoring of the titration of cryptand 4b with CH 3CO2-, Cl-, and F- in CDCl2CDCl2 at 100°C showed that the binding constants were considerably smaller than those of tripodal thiourea 5a, presumably owing to the presence of strong intramolecular hydrogen bonding in 4b. Complexation constants of tripodal receptors 5a-d with H2PO4 -, CH3CO2-, Cl-, and Br- anions were evaluated by 1H NMR and/or UV/Vis spectroscopic analysis of the titration in DMSO. Though tripodal receptors 5a,b undergo complexation with phosphate anion in a 1:1 stoichiometry, their association constants were not as large as simple reference compound 14 probably because of the steric hindrance around the binding sites and the large entropy cost for cooperative binding. Receptor 5c exhibits complexation in a 1:2 stoichiometry with H2PO4- and CH 3CO2-, whereas it forms 1:1 complexes with chloride and bromide anions because of the subtle balance between the steric hindrance and the binding ability. However, by increasing the acidity of the thiourea functionality, receptor 5d exhibited remarkably enhanced binding ability and selectivity toward H2PO4- compared to those of reference compound 15 presumably through cooperative complexation of the three binding sites to the guest anion. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
- Hisaki, Ichiro,Sasaki, Shin-Ichi,Hirose, Keiji,Tobe, Yoshito
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p. 607 - 615
(2007/10/03)
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- Studies on pyrazine derivatives, XLV: Synthesis, reactions, and tuberculostatic activity of N-methyl-N′-(pyrazine-2-carbonyl)- hydrazinecarbodithioic acid methyl ester
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Methyldithiocarbonyl derivative 2 of pyrazine-2-carboxylic acid N′-methylhydrazide 1 was synthesized by methylation of CS2 adduct. Benzylamine caused the decomposition of compound 2 to pyrazine-2-carboxylic acid benzylamide 5 and 1,3-dibenzylthiourea, 6. N-methyl-N'′-(pyrazine-2-carbonyl)-hydrazinecarbodithioic acid methyl ester 2 were evidenced to cyclize to 3-methyl-5-pyrazin-2-yl-3H-[1,3,4] oxadiazole-2-thione 8 in the presence of triethylamine. In the reactions with secondary amines such as morpholine, pyrrolidine and phenylpiperazine pyrazinoyl derivatives (9-11) of thiosemicarbazide were obtained. Hydrazine, methylhydrazine, aminoalcohols, and N-alkylamino-substituted cyclic amines reacted with cyclization to 4-substituted 1,2,4-triazole-3-thiones 12, 13, and 18-22. Synthesized compounds exhibited low tuberculostatic activity in vitro (MIC 50-100 μg/mL). Copyright Taylor & Francis Group, LLC.
- Gobis, Katarzyna,Foks, Henryk,Zwolska, Zofia,Augustynowicz-Kopec, Ewa
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p. 965 - 975
(2007/10/03)
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- Thermolysis of N,N″-1,ω-alkanediyl-bis[N′- organylthiourea] derivatives
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The course of microwave assisted or conventional thermal intramolecular heterocyclization of the title compounds has been found to be dependent on the length of the alkanediyl chain. While 1,3-propanediyl-bisthioureas 5a-c gave both 2-thioxoperhydropyrimidine-1-carbothioamides 8a-c and 8-amino-3,4,5,6- tetrahydro-1,3,7-thiadiazocine-2-thiones 10a-C, thermolysis of 1,4-butanediyl-bisthioureas 6a-c and 1,6-hexanediyl-bisthioureas 7a-c under the same conditions gave solely 9-amino-4,5,6,7-tetrahydro-1,3,8-thiadiazonine-2- thiones 11a-c and 11-amino-1-thia-3,10-diazacycloundec-10-ene-2-thiones 12a-c, respectively. Symmetric N,N′-diorganylthioureas 4a-c were formed in all cases as minor byproducts.
- Hassan, Alaa A.,Doepp, Dietrich
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p. 593 - 598
(2007/10/03)
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- Efficient synthesis of N,N′-disubstituted ureas/thioureas catalyzed by iodine
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Iodine is an efficient catalyst for the synthesis of symmetrically N,N′-disubstituted ureas/thioureas by heating respective amines or phenyl hydrazine and urea/thiourea on a preheated hot plate at 90-95°C, under solvent-free conditions. The yields are excellent, and the reactions go to complete within 5-10 min. Copyright Taylor & Francis Group, LLC.
- Pasha,Jayashankara
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p. 1787 - 1793
(2007/10/03)
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- S-SUBSTITUTED N-1- (HETERO)ARYL ALKYL-N - (HETERO)ARYL ALKYLYSOTHIOCARBAMIDES, METHOD FOR THE PRODUCTION THEREOF, PHYSIOLOGICALLY ACTIVE S-SUBSTITUTED N-1- (HETERO )ARYL ALKYL-N - (HETERO)ARYL ALKYLYSOTHIOCARBAMIDES,A PHARMACEUTICAL COMPOUND AND CURING METHOD
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The invention relates to s-substituted N-1-[(hetero)aryl]alkyl-N-1-[(hetero)aryl]alkylysothio-carbamides and the physiologically active salts and bases thereof, embodied in the form of racemic mixtures (or stereoisomer mixture) or individual optical isomers. The specific physiological activity of said compounds makes it possible to use them in the form of molecular tools. Said invention also relates to Pharmaceutical compositions, containing said compounds and to a method for preventing and curing various diseases including neurodegenerative diseases as, for example Alzheimer's disease (AD). The pharmacological effect of said compounds is based on the combined cognitive-stimulating and neuroprotective action thereof, which is produced by acting on chemo-controlled calcium channels of neurone membranes, in particular the neurones regulated by glutamate receptors of the central neural system (CNS).
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Page/Page column 12
(2008/06/13)
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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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- Expeditious method for synthesis of symmetrical 1,3-disubstituted ureas and thioureas
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Symmetrical 1,3-disubstituted ureas and symmetrical thioureas have been synthesized from corresponding isocyanates, diisocyanates, and isothiocyanates by a new versatile, simple, and quick method in the presence of tertiary amines at room temperature. The method under discussion has several advantages over the existing techniques, as it is simple to carry out, does not require complicated equipment, has a simple workup, and does not use expensive chemicals. Moreover, the yields are almost quantitative. This method has potential in commercial applications. Copyright Taylor & Francis, Inc.
- Perveen, Shahnaz,Abdul Hai, Syed M.,Khan, Rashid A.,Khan, Khalid Mohammed,Afza, Nighat,Sarfaraz, Tahira B.
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p. 1663 - 1674
(2007/10/03)
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- Self-indicating amine scavenger resins
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Self-indicating methylisocyanate resin, which functions as both a scavenger and an indicator for amines, was used for in-situ reaction monitoring and purification of a urea based library.
- Cho, Jin Ku,White, Peter D.,Klute, Wolfgang,Dean, Tony W.,Bradley, Mark
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p. 502 - 503
(2007/10/03)
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- Thermolysis of symmetrical dithiobiurea and thioureidoethylthiourea derivatives
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Microwave and thermal heterocyclization of N,N′-disubstituted hydrazinecarbothioamide 1a,b and substituted thioureidoethylthioureas 2a-c as well as 1-phenyl-3[2-(3-phenylthio-ureido)phenyl]-thiourea 6 are reported.
- Hassan, Alaa A.,Mourad, Aboul-Fetouh E.,El-Shaieb, Kamal M.,Abou-Zied, Ashraf H.,Doepp, Dietrich
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p. 535 - 541
(2007/10/03)
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- MCM-41-TBD as a new, efficient, supported heterogeneous catalyst for the synthesis of thioureas
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The preparation of thioureas, by reaction of carbon disulfide with primary amines, can be efficiently catalyzed, under heterogeneous conditions, by MCM-TBD as a new and reusable catalyst.
- Ballini, Roberto,Bosica, Giovanna,Fiorini, Dennis,Maggi, Raimondo,Righi, Paolo,Sartori, Giovanni,Sartorio, Raffaella
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p. 8445 - 8447
(2007/10/03)
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- A convenient method for the preparation of primary and symmetrical N,N'-disubstituted thioureas
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A convenient process for the preparation of both primary thioureas 2 and symmetrical N,N'-disubstituted thioureas 6 based on the condensation of amine hydrohalides 5 with potassium thiocyanate has been developed. This approach tolerates sterically bulky primary amine substrates (both chiral and achiral), and the products can usually be isolated by a simple filtration of the reaction mixture. This method is an especially attractive alternative for the synthesis of thioureas when the corresponding isothiocyanates are unavailable, or difficult to prepare. It is also worth noting that a wide variety of amine hydrohalides, which are used in this procedure, are commercially available.
- Herr,Kuhler,Meckler,Opalka
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p. 1569 - 1574
(2007/10/03)
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- 1-(Methyldithiocarbonyl)imidazole: A useful thiocarbonyl transfer reagent for synthesis of substituted thioureas
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1-(Methyldithiocarbonyl)imidazole 1 and its N-methyl quaternary salt 2 have been shown to be efficient methyldithiocarbonyl and thiocarbonyl transfer reagents for the synthesis of dithiocarbamates, symmetrical and unsymmetrical mono-, di- and tri-substituted thioureas in high yields under mild and simple non-hazardous reaction conditions. (C) 2000 Elsevier Science Ltd.
- Mohanta, Pramod K.,Dhar, Sanchita,Samal,Ila,Junjappa
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p. 629 - 637
(2007/10/03)
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- Thiocarbamoylation of amine-containing compounds 4. Reactions of tetramethylthiuram disulfide with aliphatic amines
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Thiocarbamoylation of primary and secondary aliphatic amines with tetramethylthiuram disulfide in various solvents at different temperatures was studied. At 110 °C, the reactions with primary amines afforded mixed N,N-dimethyl-N′-alkyl(cycloalkyl)thiourea
- Van Boi, Luu
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p. 2294 - 2298
(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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- Aminolysis of sulfinamoyl-esters, -sulfonamides and -sulfones. Thiooxamate and thiourea formation via a sulfine intermediate. Thiophilic or carbophilic reaction?
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The aminolysis process of sulfinamoyl derivatives was investigated with sulfinamoyl esters. An intermediate sulfine was unambiguously evidenced by formation of a Diels-Alder type adduct. The aminolysis leads to final thiooxamate products. A carbophilic addition was suggested for the reaction with secondary amines. With sulfinamoyl, -sulfones and -sulfonamides, a thiourea is formed resulting from a double aminolysis.
- Baltas,Raouf-Benchekroun,De Blic,Cazaux,Tisnes,Gorrichon,Hussein,Barthelat
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p. 14865 - 14876
(2007/10/03)
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- Enzyme induction and comparative oxidative desulfuration of isothiocyanates to isocyanates
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Enzyme induction of oxidative metabolism of isothiocyanates to isocyanates by rat liver microsomes and comparative metabolic conversion of some isothiocyanates were investigated. Metabolic activity was assayed by trapping the isocyanate metabolites from isothiocyanates with the inclusion of 2-aminofluorene to form the respective mixed ureas as previously described for the 2-naphthyl isothiocyanate. Male F344 rats were fed either a conventional grain diet for induction with Aroclor 1254 or AIN 76A diet without antioxidant beginning 2 weeks before treatment with Aroclor 1254, β- naphthoflavone, isosafrole, or phenobarbital. Enzymes responsible for the metabolism of 1- and 2-naphthyl isothiocyanate were inducible by all four agents, Aroclor being the best under the current induction protocol and metabolic conversion assay procedure. On the other hand, enzymes responsible for the metabolism of benzyl isothiocyanate were induced only by Aroclor and, to a lesser extent, by phenobarbital. For the comparative metabolic conversion studies, using the microsomes from Aroclor-treated rats fed a conventional grain diet, the rates of metabolic conversion followed the order of 1-naphthyl >> phenyl > benzyl and phenethyl >> propyl, ethyl, and methyl isothiocyanates.
- Lee, Mei-Sie
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p. 1072 - 1078
(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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