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.
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
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.
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).
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.
Efficient and versatile catalytic systems for the n-methylation of primary amines with methanol catalyzed by n-heterocyclic carbene complexes of iridium
Toyooka, Genki,Tuji, Akiko,Fujita, Ken-Ichi
, p. 4617 - 4626 (2018)
Efficient and versatile catalytic systems were developed for the N-methylation of both aliphatic and aromatic primary amines using methanol as the methylating agent. Iridium complexes bearing an Nheterocyclic carbene (NHC) ligand exhibited high catalytic performance for this type of transformation. For aliphatic amines, selective N,N-dimethylation was achieved at low temperatures (50-90 °C). For aromatic amines, selective N-monomethylation and selective N,N-dimethylation were accomplished by simply changing the reaction conditions (presence or absence of a base with an appropriate catalyst). These findings can be used to develop methods for synthesizing useful amine compounds having N-methyl or N,N-dimethyl moieties.
Facile method for the monomethylation of anilines
Ha, Hyun-Joon,Ahn, Young-Gil
, p. 1543 - 1546 (1997)
The monomethylation of anilines was achieved in high yield from the reaction of 1,3,5-triphenylhexahydro-1,3,5-triazines with BH3·S(CH3)2 followed by hydrolysis.
-
White et al.
, p. 3166 (1976)
-
Construction of interconnected acidity functions based on ortho substituted anilines and N-methylanilines as indicators
Pytela, Oldrich,Kulhanek, Jiri,Jiraskova, Eva,Nevecna, Tatjana
, p. 1638 - 1658 (2001)
The log I values of 15 mainly ortho substituted derivatives of aniline and N-methylaniline have been measured spectrophotometrically in sulfuric, perchloric, and methanesulfonic acids. A new algorithm has been suggested for construction of acidity functions enabling simultaneous and independent construction of acidity functions in various media under the condition of equal values of pKa of the same indicators in the given media. The so-called interconnected acidity functions have been constructed with using this algorithm and the log I values measured in the above media, and the pKa values have been calculated. The resulting acidity functions and pKa values agree well with the corresponding literature data.
Tandem Transformation of Nitro Compounds into N-Methylated Amines: Greener Strategy for the Utilization of Methanol as a Methylating Agent
Paul, Bhaskar,Shee, Sujan,Chakrabarti, Kaushik,Kundu, Sabuj
, p. 2370 - 2374 (2017)
A simple air- and moisture-stable, highly efficient ruthenium NNN pincer complex is reported for the first time to catalyze the tandem transformation of various aromatic and aliphatic nitro compounds into the corresponding N-methylated amines in up to 98 % yield by using methanol as a green methylating agent. Gram-scale reactions of challenging nitro substrates demonstrated the practical application aspects of this catalytic system. Importantly, the N-methylamine moiety could be smoothly introduced to various complex molecular structures without using any expensive palladium/phosphine/amine-based cross-coupling reactions.
Room-temperature copper-catalyzed arylation of dimethylamine and methylamine in neat water
Wang, Deping,Kuang, Daizhi,Zhang, Fuxing,Yang, Chunlin,Zhu, Xiaoming
, p. 714 - 718 (2015)
The first room-temperature copper-catalyzed arylations of dimethylamine and methylamine in neat water have been developed. Using a combination of CuI and 6,7-dihydroquinolin-8(5 H)-one oxime as catalyst, dimethylamine is arylated with various aryl halides to give the corresponding products in good to excellent yields. Further, this catalysis enables the selective arylation of methylamine to afford the high yields of monoarylated methylamines as the sole products.
Reaction of primary aromatic amines with alkyl carbonates over NaY faujasite: A convenient and selective access to mono-N-alkyl anilines
Selva,Tundo,Perosa
, p. 677 - 680 (2001)
At atmospheric pressure and at 130-160°C, primary aromatic amines (p-XC6H4NH2, X = H, Cl, NO2) are mono-N-alkylated in a single step, with symmetrical and asymmetrical dialkyl carbonates [ROCOOR′, R = Me, R′ = MeO(CH2)2O(CH2)2; R = R′ = Et; R = R′ = benzyl; R = R′ = allyl; R = Et, R′ = MeO(CH2)2O(CH2)2], in the presence of a commercially available NaY faujasite. No solvents are required. Mono-N-alkyl anilines are obtained with a very high selectivity (90-97%), in good to excellent yields (68-94%), on a preparative scale. In the presence of triglyme as a solvent, the mono-N-alkyl selectivity is independent of concentration and polarity factors. The reaction probably takes place within the polar zeolite cavities, and through the combined effect of the dual acid-base properties of the catalyst.
N-Alkylation of Aniline Derivatives by Use of Potassium Cation-exchanged Y-Type Zeolite
Onaka, Makoto,Umezono, Akihiro,Kawai, Motomitsu,Izumi, Yusuke
, p. 1202 - 1203 (1985)
Zeolite K-Y is effective as a promoter in the N-alkylation of aniline derivatives in comparison with γ-alumina.
-
Stoermer,Hoffmann
, p. 2529 (1898)
-
A convenient one pot procedure for N-methylation of aromatic amines using trimethyl orthoformate
Padmanabhan, Seetharamaiyer,Reddy, N. Laxma,Durant, Graham J.
, p. 691 - 699 (1997)
Aromatic amines react with trimethyl orthoformate in the presence of concentrated sulfuric acid followed by acid hydrolysis to afford mono methylated amines in moderate to good yields.
To what extent can a conjugation between two pairs of peri-nitro and peri-amino groups be realized through the naphthalene core?
Ozeryanskii, Valery A.,Filatova, Ekaterina A.,Pozharskii, Alexander F.,Shevchuk, Dmitrii A.,Sorokin, Vladimir I.
, p. 492 - 502 (2013)
Through-conjugation for a wide range of 1,8-diamino-4,5-dinitronaphthalenes (N-acylated, N-alkylated, N,N′-bridged, N-heterocyclic, and N-deprotonated compounds) was for the first time quantified in solution by means of ultraviolet-visible and proton nucl
INTERVENTION OF N,N-DIMETHYLANILINIUM CATION RADICAL IN THE POLONONOVSKI TYPE REACTION OF N,N-DIMETHYLANILINE N-OXIDE CATALYZED BY MESO-TETRAPHENYLPORPHINATOIRON/IMIDAZOLE
Fujimori, Ken,Takata, Toshikazu,Fujiwara, Seiichi,Kikuchi, Osamu,Oae, Shigeru
, p. 1617 - 1620 (1986)
Meso-tetraphenylporphinatoiron(III)/imidazole catalyzes the Polonovski type reaction of substituted N,N-dimethylaniline N-oxides to give mixtures of N-demethylated and N-deoxygenated products.Effect of substituent on the turnover number and the ratio of the demethylation to the deoxygenation, and other observations suggest that the Polonovski type N-demethylation reaction takes place via the rate determining N,N-dimethylanilinium cation radical formation.
Methanol dehydrogenation by iridium N-heterocyclic carbene complexes
Campos, Jesús,Sharninghausen, Liam S.,Manas, Michael G.,Crabtree, Robert H.
, p. 5079 - 5084 (2015)
A series of homogeneous iridium bis(N-heterocyclic carbene) catalysts are active for three transformations involving dehydrogenative methanol activation: acceptorless dehydrogenation, transfer hydrogenation, and amine monoalkylation. The acceptorless dehydrogenation reaction requires base, yielding formate and carbonate, as well as 2-3 equivalents of H2. Of the few homogeneous systems known for this reaction, our catalysts tolerate air and employ simple ligands. Transfer hydrogenation of ketones and imines from methanol is also possible. Finally, N-monomethylation of anilines occurs through a borrowing hydrogen reaction. Notably, this reaction is highly selective for the monomethylated product.
-
Borch,R.F.,Hassid,A.I.
, p. 1673 - 1674 (1972)
-
Borane-Trimethylamine Complex as a Reducing Agent for Selective Methylation and Formylation of Amines with CO2
Zhang, Yanmeng,Zhang, He,Gao, Ke
supporting information, p. 8282 - 8286 (2021/10/25)
We report herein that a borane-trimethylamine complex worked as an efficient reducing agent for the selective methylation and formylation of amines with 1 atm CO2 under metal-free conditions. 6-Amino-2-picoline serves as a highly efficient catalyst for the methylation of various secondary amines, whereas in its absence, the formylation of primary and secondary amines was achieved in high yield with high chemoselectivity. Mechanistic studies suggest that the 6-amino-2-picoline-borane catalytic system operates like an intramolecular frustrated Lewis pair to activate CO2.
