- Electrochemical Hofmann rearrangement mediated by NaBr: Practical access to bioactive carbamates
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An electrochemical Hofmann rearrangement is reported. With the mediation of NaBr, highly corrosive and toxic halogens are avoided. Moreover, this efficient and green approach is well compatible with a broad range of amides, including several commercial medicine derivatives, and provides direct access to synthetically useful carbamates. The synthetic utility of this method is also demonstrated by the preparation of 15N labeling carbamate and gram-scale synthesis of Amantadine.
- Li, Lijun,Xue, Mengyu,Yan, Xin,Liu, Wenmin,Xu, Kun,Zhang, Sheng
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p. 4615 - 4618
(2018/07/06)
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- Chemoselective synthesis of carbamates using CO2 as carbon source
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Synthesis of carbamates directly from amines using CO2 as the carbon source is a straightforward and sustainable approach. Herein, we describe a highly effective and chemoselective methodology for the synthesis of carbamates at room temperature and atmosp
- Riemer, Daniel,Hirapara, Pradipbhai,Das, Shoubhik
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p. 1916 - 1920
(2018/08/17)
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- An efficient one-pot synthesis of: N, N ′-disubstituted ureas and carbamates from N -acylbenzotriazoles
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A facile and high-yielding one-pot synthesis of carbamates and N,N′-disubstituted symmetrical ureas from N-acylbenzotriazoles has been devised. It is believed that, the intermediate acyl-azide undergo Curtius rearrangement and in different solvents gives different products i.e. carbamates in alcohols and N,N′-disubstituted symmetrical urea in THF.
- Singh, Anoop S.,Kumar, Dhananjay,Mishra, Nidhi,Tiwari, Vinod K.
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p. 84512 - 84522
(2016/10/12)
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- C,N-chelated organotin(IV) compounds as catalysts for transesterification and derivatization of dialkyl carbonates
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The potential catalytic activity of selected C,N-chelated organotin(IV) compounds (e.g. halides and trifluoroacetates) for derivatization of both dimethyl carbonate (DMC) and diethyl carbonate (DEC) was investigated. Some tri-, di- and monoorganotin(IV) species (LCN(n-Bu)2SnCl (1), LCN(n-Bu)2SnCl.HCl (1a), LCN(n-Bu) 2SnI (2), LCNPh2SnCl (3), LCNPh 2SnI (4), LCN(n-Bu)SnCl2 (5), L CNSnBr3 (6) and [LCNSn(OC(O)CF 3)]2(μ-O)(μ-OC(O)CF3)2 (7)) bearing the LCN moiety (LCN = 2-(N,N-dimethylaminomethyl) phenyl-) were assessed as catalysts for reactions of both DMC and DEC with various substituted anilines. The catalytic activities of 4 and 7 for derivatization of DMC with p-substituted phenols were studied for comparison with the standard base K2CO3/Silcarbon K835 catalyst (catalyst 8). The composition of resulting reaction mixtures was monitored by multinuclear NMR spectroscopy, GC and GC-MS techniques. In general, catalysts 1, 3 and 7 exhibited the highest catalytic activity for all reactions studied, while some of them yielded selectively carbonates, carbamates, lactam or substituted urea. Copyright
- Weidlich, Tomas,Dusek, Libor,Vystrcilova, Barbora,Eisner, Ales,Svec, Petr,Ruzicka, Ales
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experimental part
p. 293 - 300
(2012/10/07)
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- Design and synthesis of novel stiripentol analogues as potential anticonvulsants
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A series of stiripentol (STP) analogues namely, 2-[(1E)-1-(1,3-benzodioxol- 5-yl)-4,4-dimethylpent-1-en-3-ylidene]-N-(aryl/H)hydrazinecarboxamides 7a-h, (±)-(5RS)-N-(aryl/H)-(1,3-benzodioxol-5-yl)-3-tert-butyl-4, 5-dihydro-1H-pyrazole-1-carboxamides (±)-8a-h, and (±)-[(5RS)-(1, 3-benzodioxol-5-yl)-3-tert-butyl-4,5-dihydro-1H-pyrazol-1-yl](aryl)methanones (±)-13a-f was synthesized by adopting appropriate synthetic routes and was pharmacologically evaluated in the preliminary anticonvulsant screens. The selected bioactive new chemical entities were subjected to ED50 determination and neurotoxicity evaluation. The most active congeners are 7h in MES screen and (±)-13b in scPTZ screen which displayed ED50 values of 87 and 110 mg/kg, respectively, as compared to that of STP (ED 50 = 277.7 and 115 mg/kg in MES and scPTZ, respectively).
- Aboul-Enein, Mohamed N.,El-Azzouny, Aida A.,Attia, Mohamed I.,Maklad, Yousreya A.,Amin, Kamilia M.,Abdel-Rehim, Mohamed,El-Behairy, Mohammed F.
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experimental part
p. 360 - 369
(2012/03/11)
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- Copper-catalyzed coupling of arylboronic acids with potassium cyanate: A new approach to the synthesis of aryl carbamates
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The copper-catalyzed coupling of aromatic boronic acids with potassium cyanate in the presence of an alcohol has been employed for the synthesis of arylcarbamates. This simple and highly efficient approach can be carried out in air at room temperature and, importantly, no base, ligand, or additive is required. Copyright
- Kianmehr, Ebrahim,Baghersad, Mohammad Hadi
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supporting information; experimental part
p. 2599 - 2603
(2011/11/29)
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- MONOACYLGLYCEROL LIPASE INHIBITORS FOR MODULATION OF CANNABINOID ACTIVITY
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Disclosed are compounds and compositions that inhibit the action of monoacylglycerol lipase (MGL) and fatty acid amide hydrolase (FAAH), methods of inhibiting MGL and FAAH, methods of modulating cannabinoid receptors, and methods of treating various disorders related to the modulation of cannabinoid receptors.
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Page/Page column 104
(2009/05/28)
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- FATTY ACID AMIDE HYDROLASE INHIBITORS
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Disclosed are compounds of formula R-X-Y that may be used to inhibit the action of fatty acid amide hydrolase (FAAH). Inhibition of fatty acid amide hydrolase (FAAH) will slow the normal degradation and inactivation of endogenous cannabinoid ligands by FAAH hydrolysis and allow higher levels of those endogenous cannabinergic ligands to remain present. These higher levels of endocannabinoid ligands provide increased stimulation of the cannabinoid CBl and CB2 receptors and produce physiological effects related to the activation of the cannabinoid receptors. They will also enhance the effects of other exogenous cannabinergic ligands and allow them to produce their effects at lower concentrations as compared to systems in which fatty acid amide hydrolase (FAAH) action is hot inhibited. Thus, a compound that inhibits the inactivation of endogenous cannabinoid ligands by fatty acid amide hydrolase (FAAH) may increase the levels of endocannabinoids and, thus, enhance the activation of cannabinoid receptors. Thus, the compound may not directly modulate the cannabinoid receptors but has the effect of indirectly stimulating the cannabinoid receptors by increasing the levels of endocannabinoid ligands. It may also enhance the effects and duration of action of other exogenous cannabinergic ligands that are administered in order to elicit a cannabinergic response.
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Page/Page column 66
(2008/06/13)
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- Synthesis of some heterocycle containing urea derivatives and their anti-viral activity
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Some new isoindol heterocyclic ureas (6a-6i) have been synthesized using N-aminophthalimide (2) and ethyl N-monosubstituted/ethyl N,N-disubstituted carbamate (5a-5i). All the newly synthesized final compounds have been evaluated for their anti-viral activities against a variety of viruses. The compound (6f) with the methoxy substituent showed reasonably better activity as compared to the standard drugs against all the viruses (cf. Tables 1, 2 and 3). Further, all the products (6a-6i) were found to be active against Vesicular stomatitis virus, Coxsackie virus B4 and Respiratory syncytical virus (cf. Table 2) and the compounds (6h) and (6i) displayed better antiviral activity in comparison to Brivudin and (S)-DHPA (cf. Table 3).
- Verma, Majusha,Singh, Krishna N.,Clercq, Erik D.
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- A simple method for the synthesis of carbamates
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A new method for carbamate synthesis using aryl and alkylamines with sodium hydride and diethylcarbonate in dry benzene is described.
- Angeles,Santillan,Martinez,Ramirez,Moreno,Salmon,Martinez
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p. 2441 - 2447
(2007/10/02)
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