100-15-2Relevant articles and documents
Some properties of 1-(nitrophenyl)-aminobenzimidazoles
Dyablo,Pozharskii,Shkurupii
, p. 37 - 39 (2000)
The chemical properties of previously synthesized 1-[2(4)-nitrophenyl]aminobenzimidazoles, in particular, alkylation at the NH group, thiolation, and reduction were studied.
Unusual Rate-limiting Proton Transfer in the Acid-catalysed Reactions of N-Nitroso Compounds
Al-Kaabi, Sharifa S.,Hallett, Geoffrey,Meyer, Thomas A.,Williams, D. Lyn H.
, p. 1803 - 1808 (1984)
For both N-methyl-N-nitrosoaniline and N-nitrosodiphenylamine, the catalytic effect of halide ion, thiocyanate ion, and thiourea in the denitrosation reaction in acid solution disappears at high nucleophile concentrations.This suggests a change to an earlier rate-limiting step.The data, including the variation of rate constant with acidity, are quantitatively in accord with a reaction mechanism involving protonation of the nitosamine followed by nucleophilic attack, either stage being rate limiting, depending on the reactivity and concentration of the nucleophile.The kinetic solvent isotope effect kH2O/kD2O decreases from 1.59 at 0.43M-thiourea to 0.71 at 0.015M-thiourea, which is consistent with a change from general acid catalysis at high to specific hydrogen ion catalysis at low .Substituent effects at the amino-nitrogen atom and also in the 4-position of a phenyl substituent are very amall, the largest effect being a three-fold reduction in rate constant effected by a 4-NO2 group.These results are in accord with the known dipolar nature of nitrosamines.There is a close analogy between this system and the acid-catalysed cleavage reaction of carbamate derivatives.A similar mechanism is proposed involving a pre-association of the reactants forming a hydrogen-bonded intermediate.
Methanolysis of thioamide promoted by a simple palladacycle is accelerated by 108 over the methoxide-catalyzed reaction
Liu, C. Tony,Maxwell, Christopher I.,Pipe, Stephanie G.,Neverov, Alexei A.,Mosey, Nicholas J.,Brown, R. Stan
, p. 20068 - 20071 (2011)
Palladacycle 1 catalyzes the methanolytic cleavage of N-methyl-N-(4- nitrophenyl)thiobenzamide (4) via a mechanism involving formation of a Pd-bound tetrahedral intermediate (TI). The rate constant for decomposition of the complex formed between 1, methox
The Reaction of Benzenesulfenanilides with Lewis Acids: Involvement of Radical Cation Intermediates.
Grossi, Loris,Montevecchi, Carlo
, p. 9095 - 9104 (1993)
The 4'-substituted N-methylbenzenesulfenanilides 1a-c react with Lewis acids, including BF3, AlCl3 and GaCl3, to afford the radical cation intermediates 9a-c, some of which could be detected by e.p.r. spectroscopy.Thus, the 4'-methoxy substituted compound 1a gave the fairly persistent radical cation 9a.In contrast, the radical cation 9b, derived from the 4'-nitro substituted compound 4b, was not detected apparently because it decayed too rapidly forming the very stable radical cation 11b, intermediate in the formation of the rearranged sulfide 10b.The radical intermediates 9a-c react with cyclohexene to give the 1,2-adducts 4a-c, 5 and 6 which are believed to be formed from either the thiiranium ion 7b or the sulfurane 8a,c.
Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2
Suárez-Castillo, Oscar R.,Montiel-Ortega, Luis Alberto,Meléndez-Rodríguez, Myriam,Sánchez-Zavala, Maricruz
, p. 17 - 20 (2007)
An efficient, simple protocol for the selective cleavage of a variety of N-alkoxycarbonyl protecting groups by t-BuNH2/MeOH is described. The scope of the procedure was explored for a series of indole, aniline and pyrrolidine carbamate derivatives containing other potentially reactive functional groups affording a clean cleavage of the carbamate group.
Oxidative N-demethylation of N,N-dimethylanilines catalysed by lignin peroxidase: A mechanistic insight by a kinetic deuterium isotope effect study
Baciocchi, Enrico,Gerini, Maria Francesca,Lanzalunga, Osvaldo,Lapi, Andrea,Mancinelli, Simona,Mencarelli, Paolo
, p. 393 - 394 (2000)
Lignin peroxidase can catalyse the N-demethylation of N,N- dimethylanilines by an electron transfer mechanism, where the deprotonation of the intermediate radical cation is also an enzymatic process.
Synthesis of some heterocycle containing urea derivatives and their anti-viral activity
Verma, Majusha,Singh, Krishna N.,Clercq, Erik D.
, p. 11 - 22 (2006)
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).
Highly selective hydrogenation of amides catalysed by a molybdenum pincer complex: Scope and mechanism
Leischner, Thomas,Artús Suarez, Lluis,Spannenberg, Anke,Junge, Kathrin,Nova, Ainara,Beller, Matthias
, p. 10566 - 10576 (2019)
A series of molybdenum pincer complexes has been shown for the first time to be active in the catalytic hydrogenation of amides. Among the tested catalysts, Mo-1a proved to be particularly well suited for the selective C-N hydrogenolysis of N-methylated formanilides. Notably, high chemoselectivity was observed in the presence of certain reducible groups including even other amides. The general catalytic performance as well as selectivity issues could be rationalized taking an anionic Mo(0) as the active species. The interplay between the amide CO reduction and the catalyst poisoning by primary amides accounts for the selective hydrogenation of N-methylated formanilides. The catalyst resting state was found to be a Mo-alkoxo complex formed by reaction with the alcohol product. This species plays two opposed roles-it facilitates the protolytic cleavage of the C-N bond but it encumbers the activation of hydrogen.
Methylation of aniline and its derivatives with dimethyl carbonate in the presence of binder-free micro-, meso-, and macroporous zeolites KNaX, NaY, and HY
Khusnutdinov,Shchadneva,Mayakova, Yu. Yu.,Ardieva,Khazipova,Kutepov
, p. 1565 - 1570 (2016)
Aniline and its derivatives undergo methylation when treated with dimethyl carbonate in the presence of binder-free micro-, meso-, and macroporous zeolites KNaX, NaY, and HY leading to the formation of N-methyl- and N,N-dimethylanilines.
Synergistic effect of cyclodextrin-based binuclear complexes in the hydrolysis of amide
Yan, Jia-Ming,Atsumi, Masato,Yuan, De-Qi,Fujita, Kahee
, p. 1825 - 1828 (2000)
Novel cyclodextrin-based binuclear metal complexes have been prepared and proved to be far more efficient than their mononuclear complexes in promoting amide hydrolysis. (C) 2000 Elsevier Science Ltd.
