cas 119-68-6, N-METHYLANTHRANILIC ACID | Articles data

Articles about 119-68-6Total 39 be found

Article title
Article abstract
Author
Journal number and time
Download

-
-
Pachter,I.J. et al.
p. 5187 - 5193
(1960)
Read Online

Use of ultrasound in the synthesis of 2-(alkylamino)benzoic acids in water
The synthesis of substituted 2-(alkylamino)benzoic acids using the Ullmann condensation with water as the solvent and utilizing ultrasound irradiation was achieved with high yields in a short reaction time. Georg Thieme Verlag Stuttgart.
Pellón, Rolando F.,Estévez-Braun, Ana,Docampo, Maite L.,Martín, Ana,Ravelo, Angel G.
p. 1606 - 1608
(2005)
Read Online

Toward the Rational Design of Universal Dual Polarity Matrix for MALDI Mass Spectrometry
A series of novel anthranilic acid derivatives I-IV, of which COOH-NH2 (I) and COOH-NHMe (IV) are endowed with acid and base bifunctionality, were designed and synthesized for matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry applications in dual polarity molecular imaging of biological samples, particularly for lipids. The heat of protonation, deprotonation, and proton transfer reaction as well as the capability of analyzing biomolecules in both positive and negative ion modes for I-IV were systematically investigated under standard 355 nm laser excitation. The results indicate correlation between dual polarity and acid-base property. Further, COOH-NHMe (IV) showed a unique performance and was successfully applied as the matrix for MALDI-TOF mass spectrometry imaging (MSI) for studying the mouse brain. Our results demonstrate the superiority of COOH-NHMe (IV) in detecting more lipid and protein species compared to commercially available matrices. Moreover, MALDI-TOF MSI results were obtained for lipid distributions, making COOH-NHMe (IV) a potential next generation universal matrix.
Chou, Pi-Tai,Hsu, Cheng-Chih,Huang, Chun-Ying,Huang, Penghsuan,Lee, Chuping,Lin, Li-En,Lin, Ta-Chun,Yang, Ethan
p. 7139 - 7145
(2020)
Read Online

Platinum(iv)-azido monocarboxylato complexes are photocytotoxic under irradiation with visible light
Complexestrans,trans,trans-[Pt(N3)2(OH)(OCOR)(py)2] where py = pyridine and where OCOR = succinate (1); 4-oxo-4-propoxybutanoate (2) andN-methylisatoate (3) have been synthesized by derivation oftrans,trans,trans-[Pt(OH)2(N3)2(py)2] (4) and characterised by NMR and EPR spectroscopy, ESI-MS and X-ray crystallography. Irradiation of1-3with green (517 nm) light initiated photoreduction to Pt(ii) and release of the axial ligands at a 3-fold faster rate than for4. TD-DFT calculations showed dissociative transitions at longer wavelengths for1compared to4. Complexes1and2showed greater photocytotoxicity than4when irradiated with 420 nm light (A2780 cell line IC50values: 2.7 and 3.7 μM) and complex2was particularly active towards the cisplatin-resistant cell line A2780cis (IC503.7 μM). Unlike4, complexes1-3were phototoxic under green light irradiation (517 nm), with minimal toxicity in the dark. A pKa(H2O) of 5.13 for the free carboxylate group was determined for1, corresponding to an overall negative charge during biological experiments, which crucially, did not appear to impede cellular accumulation and photocytotoxicity.
Butler, Jennifer S.,Clarkson, Guy,Farrer, Nicola J.,Habtemariam, Abraha,Romero, Mar?a J.,Romero-Canelón, Isolda,Sadler, Peter J.,Salassa, Luca,Shaili, Evyenia,Woods, Julie A.
p. 10593 - 10607
(2021)
Read Online

Melatonin derivatives combat with inflammation-related cancer by targeting the Main Culprit STAT3
The combination between two well-studied bioactive compounds melatonin and salicylic acid with proper modifications unexpectedly creates a sharp pair of “scissors” cutting off the vicious connection between inflammation and cancer by targeting a key contributor Signal Transducers and Activators of Transcription 3 (STAT3) in the two pathological processes. A representative compound P-3 with IC50 values on each tested cell line ranging from 7.37 to 18.62 μM among the designed melatonin derivatives is equipped with the ability of curbing inflammation-promoting cancer by down-regulating the expression, activation and nuclear translocation of STAT3, breaking the feedforward loop of STAT3 activation by decreasing the expression of pro-tumorigenic cytokines, and inducing cell apoptosis through ROS triggered Cyto-c/Caspase-3 pathway. This study suggests that the melatonin derivative P-3 is likely to become a promising chemical structure for developing the novel anti-cancer agents taking effect through hindering the mutual-promoting processes between inflammation and cancer.
Ma, Shumeng,Zhu, Longqing,Fan, Xiaohong,Luo, Tian,Liu, Dan,Liang, Ziyi,Hu, Xiaoling,Shi, Tao,Tan, Wen,Wang, Zhen
(2020/12/02)

Palladium-Catalyzed Multistep Tandem Carbonylation/N-Dealkylation/Carbonylation Reaction: Access to Isatoic Anhydrides
A novel and efficient synthesis of isatoic anhydride derivatives was developed via palladium-catalyzed multistep tandem carbonylation/N-dealkylation/carbonylation reaction with alkyl as the leaving group and tertiary anilines as nitrogen nucleophiles. This approach features good functional group compatibility and readily available starting materials. Furthermore, it provided a convenient approach for the synthesis of biologically and medicinally useful evodiamine.
Wang, Shoucai,Li, Xuan,Zang, Jiawang,Liu, Meichen,Zhang, Siyu,Jiang, Guangbin,Ji, Fanghua
p. 2672 - 2679
(2020/02/04)

Catalytic Alkylation Using a Cyclic S-Adenosylmethionine Regeneration System
S-Adenosylmethionine-dependent methyltransferases are versatile tools for the specific alkylation of many compounds, such as pharmaceuticals, but their biocatalytic application is severely limited owing to the lack of a cofactor regeneration system. We report a biomimetic, polyphosphate-based, cyclic cascade for methyltransferases. In addition to the substrate to be methylated, only methionine and polyphosphate have to be added in stoichiometric amounts. The system acts catalytically with respect to the cofactor precursor adenosine in methylation and ethylation reactions of selected substrates, as shown by HPLC analysis. Furthermore, 1H and 13C NMR measurements were performed to unequivocally identify methionine as the methyl donor and to gain insight into the selectivity of the reactions. This system constitutes a vital stage in the development of economical and environmentally friendly applications of methyltransferases.
Mordhorst, Silja,Siegrist, Jutta,Müller, Michael,Richter, Michael,Andexer, Jennifer N.
supporting information
p. 4037 - 4041
(2017/03/27)

Acetic Acid Accelerated Visible-Light Photoredox Catalyzed N-Demethylation of N,N-Dimethylaminophenyl Derivatives
N,N-Dimethylaminophenyl moiety is a common fragment in medicinal chemistry as several pharmaceuticals bearing this privileged motif are on the market and under clinical evaluation. Oxidative N-demethylation is generally regarded as the major metabolic pathway. However, pharmacokinetics, metabolites studies as well as the further structural modification are precluded by the impracticality of chemical synthesis. Here we report that acetic acid can significantly accelerate visible-light photoredox catalyzed N-demethylation of N,N-dimethylaminophenyl derivatives. This approach is easy for large scale reaction and even for potential industrial manufacture. (Figure presented.).
Wu, Guolin,Li, Yazhen,Yu, Xuemei,Gao, Yu,Chen, Haijun
supporting information
p. 687 - 692
(2017/02/23)

Palladium-Catalyzed Ortho-Selective C-H Oxidative Carbonylation of N-Substituted Anilines with CO and Primary Amines for the Synthesis of o-Aminobenzamides
An efficient, one-pot strategy with high selectivity and high atom economy for the synthesis of o-aminobenzamides has been developed via palladium-catalyzed ortho-selective C-H oxidative carbonylation of N-substituted anilines with CO and primary amines. A wide range of N-substituted anilines and primary amines can be tolerated in this transformation to afford the corresponding o-aminobenzamides in moderate to excellent yields under mild conditions.
Zhang, Xiaopeng,Dong, Shuxiang,Niu, Xueli,Li, Zhengwei,Fan, Xuesen,Zhang, Guisheng
supporting information
p. 4634 - 4637
(2016/09/28)

Investigation into the stability and reactivity of the pentacyclic alkaloid dehydroevodiamine and the benz-analog thereof
Limited synthetic approaches to obtain the biologically active alkaloid dehydroevodiamine (DHED) are known to date. Undesired demethylation in the most widely applied route was found to be a hampering side reaction for the benz-DHED derivative leading to a quinazolinone, which represents a benz-rutaecarpine derivative. For rutaecarpine, a related plant alkaloid, many different synthetic approaches have been described. Alternative reaction procedures to obtain DHED such as methylation of rutaecarpine and oxidation of evodiamine were investigated to make DHED more easily accessible and the latter method proved to be the most successful one. Furthermore, the remarkable equilibrium between the ring closed quinazolinium and the ring open form of the compounds was systematically investigated by UV-vis measurements. The ring open form and the quinazolinium salt, form the same species when incubated in buffer solution for 24 h. A better soluble form, i.e., 'hydroxyevodiamine', seems to represent the biologically active form that has not yet been described.
Wehle, Sarah,Espargaró, Alba,Sabaté, Raimon,Decker, Michael
p. 2535 - 2543
(2016/04/26)

N-methyl isatin a process for the preparation of acid anhydride
The invention provides a method for preparing N-methyl isatoic anhydride. The method comprises simple steps, is simple and convenient to operate, and is suitable for industrial production, and the raw materials are cheap and are easily available. The method comprises following steps of firstly taking anhydrous potassium carbonate as acid-binding agent and copper powder as a catalyst, carrying out a condensation reaction on o-chlorobenzoic acid and methylamine so as to obtain N-methyl o-aminobenzoic acid, and carrying out cyclization through condensation by adopting triphosgene and N-methyl o-aminobenzoic acid, so as to prepare the N-methyl isatoic anhydride.
-
Paragraph 0010; 0028-0029

(2017/03/08)

Optimisation of LRRK2 inhibitors and assessment of functional efficacy in cell-based models of neuroinflammation
LRRK2IN1 is a highly potent inhibitor of leucine-rich repeat kinase 2 (LRRK2, IC50 = 7.9 nM), an established target for treatment of Parkinson's disease. Two LRRK2IN1 analogues 1 and 2 were synthesised which retained LRRK2 inhibitory activity (1: IC50 = 72 nM; 2: IC50 = 51 nM), were predicted to have improved bioavailability and were efficacious in cell-based models of neuroinflammation. Analogue 1 inhibited IL-6 secretion from LPS-stimulated primary human microglia with EC50 = 4.26 μM. In order to further optimize the molecular properties of LRRK2IN1, a library of truncated analogues was designed based on docking studies. Despite lacking LRRK2 inhibitory activity, these compounds show antineuroinflammatory efficacy at micromolar concentration. The compounds developed were valuable tools in establishing a cell-based assay for assessing anti-neuroinflammatory efficacy of LRRK2 inhibitors. Herein, we present data that IL-1β stimulated U87 glioma cell line is a reliable model for neuroinflammation, as data obtained in this model were consistent with results obtained using primary human microglia and astrocytes.
Munoz, Lenka,Kavanagh, Madeline E.,Phoa, Athena F.,Heng, Benjamin,Dzamko, Nicolas,Chen, Ew-Jun,Doddareddy, Munikumar Reddy,Guillemin, Gilles J.,Kassiou, Michael
supporting information
p. 29 - 34
(2015/03/30)

The effect of hydrogen bond on Br?nsted acid-catalyzed intramolecular hydroamination of unfunctionalized olefins
The catalytic activity of benzoic acid could be increased by introducing a hydrogen bond donor group at the ortho-position. Preliminary DFT calculation indicated that the activation of CC double bond was realized by the action of both the carboxyl group and the hydrogen bond donor. The amino group was brought to the activated CC bond by the interaction between the carboxyl oxygen and amino proton. This interaction also increased the nucleophilicity of the amino group. Thus, in the presence of 20 mol % of 2-(trifluoromethanesulfonamido)benzoic acid, intramolecular hydroamination of unfunctionalized olefins gave the corresponding products in up to 95% isolated yields.
Li, Ting-Ting,Liu, Gong-Qing,Wang, Yu-Mei,Cui, Bin,Sun, Hui,Li, Yue-Ming
p. 7003 - 7009
(2015/08/19)

Design, synthesis, and evaluation of novel 1-methyl-3-substituted quinazoline-2,4-dione derivatives as antimicrobial agents
A series of novel 1-methyl-3-substituted quinazoline-2,4-dione derivatives was designed, synthesized, and evaluated for their antimicrobial activities against six strains of bacteria and five fungi in vitro. The synthesized compounds were characterized by spectral methods. The bioactive assays showed that most of the compounds exhibited moderate antimicrobial activities against the tested strains. Springer Science+Business Media 2013.
Ji, Qing-Gang,Yang, Dan,Deng, Qiao,Ge, Zhi-Qiang,Yuan, Lv-Jiang
p. 2169 - 2177
(2014/05/06)

Synthesis of 1-substituted 4(1H)-quinazolinones under solvent-free conditions
(Chemical Equation Presented) Heating a mixture of 2-(N-alkylamino)benzoic acids, triethyl orthoformate, and ammonium acetate under solvent-free conditions generated 1-substituted 4(1H)- quinazolinones in 73-99% yields. Moreover, a possible reaction pathway was proposed. Copyright Taylor & Francis Group, LLC.
Wang, Yao,Zhang, Mei,Cao, Shengli,Lin, Huihui,Gao, Man,Li, Zhongfeng
experimental part
p. 2715 - 2727
(2012/07/14)

Palladium-catalyzed regioselective carbonylation of C-H bonds of N -alkyl anilines for synthesis of isatoic anhydrides
A Pd-catalyzed regioselective C-H bond carbonylation of N-alkyl anilines for the synthesis of isatoic anhydrides has been developed. The key Pd-catalyst intermediate has been isolated and characterized. This novel Pd-catalyzed carbonylation reaction tolerates a wide range of functional groups and is a reliable method for the rapid elaboration of readily available N-alkyl anilines into a variety of substituted isatoic anhydrides under mild conditions.
Guan, Zheng-Hui,Chen, Ming,Ren, Zhi-Hui
p. 17490 - 17493,4
(2020/09/16)

A ligand-free and base-free copper catalyzed reaction: Arylation of ammonia and primary amines as their acetate salts
A ligand-free, base-free copper catalyzed arylation of ammonia and primary amines as their corresponding acetate salts are established. The Carboxylate group is believed to be catalyzing the arylation of ammonia. This reaction is specific for primary amines.
Siddegowda, Maravanahalli S.,Yathirajan, Hemmige S.,Ramakrishna, Ramesha A.
supporting information
p. 5219 - 5222
(2012/11/07)

Screening of ligands for the Ullmann synthesis of electron-rich diaryl ethers
In the search for new ligands for the Ullmann diaryl ether synthesis, permitting the coupling of electron-rich aryl bromides at relatively low temperatures, 56 structurally diverse multidentate ligands were screened in a model system that uses copper iodide in acetonitrile with potassium phosphate as the base. The ligands differed largely in their performance, but no privileged structural class could be identified.
Otto, Nicola,Opatz, Till
supporting information; experimental part
p. 1105 - 1111
(2012/09/07)

A facile and practical copper powder-catalyzed, organic solvent-and ligand-free ullmann amination of aryl halides
A facile and practical method that the copper powder-catalyzed Ullmann amination of aryl halides with aqueous methylamine under organic solvent-and ligand-free condition at 100 °C and in air gave N-arylamines as sole products in good to excellent yields. The presence of a small amount of air is essential. Other aliphatic primary amines show good to very high reactivity. Secondary amines and aniline are not reactive. Sensitive substituents (i.e., CHO, MeCO, CN and Cl) are tolerable in the reaction.
Jiao, Jiao,Zhang, Xi-Ru,Chang, Ning-Hui,Wang, Jie,Wei, Jun-Fa,Shi, Xian-Ying,Chen, Zhan-Guo
supporting information; experimental part
p. 1180 - 1183
(2011/04/24)

Layered double hydroxide-supported l-methionine-catalyzed chemoselective o-methylation of phenols and esterification of carboxylic acids with dimethyl carbonate: A "green" protocol
" Chemical equation presented" Simple methodology: A layered double hydroxide-supported L-methionine (LDH-Met) catalyst is designed in a simple methodology to explore its synthetic utility in biologically relevant reactions. The organocatalyst is characterized by FT-IR, TGA/DTA, powder XRD, and EDX spectroscopic techniques. This material has been successfully utilized for the preparation of aryl methyl ethers and esters from the corresponding phenols and carboxylic acids, respectively, in moderate to high yields (see scheme).
Dhakshinamoorthy, Amarajothi,Sharmila, Alagarsamy,Pitchumani, Kasi
supporting information; experimental part
p. 1128 - 1132
(2010/06/13)

Efficient copper-catalyzed synthesis of N-alkylanthranilic acids via an ortho-substituent effect of the carboxyl group of 2-halobenzoic acids at room temperature
We have developed an efficient copper-catalyzed method for the synthesis of N-alkylanthranilic acids. The protocol uses inexpensive copper(I) iodide/racemic 1,1'-binaphthyl-2,2'-diol (rac-BINOL) as the catalyst/ligand system, readily available 2-halobenzoic acids and aliphatic amines as the starting materials, the coupling reactions were performed at room temperature, and various functionalities in the substrates were tolerated.
Zeng, Liang,Fu, Hua,Qiao, Renzhong,Jiang, Yuyang,Zhao, Yufen
supporting information; experimental part
p. 1671 - 1676
(2011/02/25)

Synthesis of 4-hydroxy-3-formylideneamino-lH/methyl/phenylquinolin-2-ones
An efficient method for the synthesis of 4-hydroxy-3-formylideneamino-l H/methyl/phenylquinolin-2-ones by the condensation of corresponding 4-hydroxy-3-formyl-l///methyl/phenylquinolin-2-one with substituted anilines/aliphatic primary amines is reported. The carboxaldehyde in turn is prepared starting either from substituted anilines or benzoic acid. The structures of compounds are established by the elemental analysis and spectral data.
Bhudevi,Ramana,Mudiraj, Anwita,Reddy
experimental part
p. 255 - 260
(2009/12/03)

New gas-phase cascade reactions of stabilized phosphorus ylides leading to ring-fused indoles and to quinolines
(Chemical Equation Presented) Gas-phase cyclization processes of stabilized phosphorus ylides bearing a suitably substituted 2-aminophenyl group lead efficiently either to 3-substituted quinolines or benzo[c]-carbazole and heterocyclic-fused analogues depending on the substituents present.
Aitken, R. Alan,Murray, Lorna
supporting information; experimental part
p. 9781 - 9783
(2009/04/06)

Ultrasound-promoted reaction of 2-chlorobenzoic acids and aliphatic amines
An improvement to the use of DMF as a solvent for the condensation of 2-chlorobenzoic acids with aliphatic primary or secondary amines was described. A number of alkylaminobenzoic acids and dialkylaminobenzoic acids were synthesized in acceptable-to-good yield. The advantages of this procedure include readily available substrates, the use of an inexpensive copper powder without taking any precautions to exclude moisture under mild conditions and experimental ease. Furthermore, this condensation could also be achieved under nonclassical conditions by using ultrasonic irradiation at room temperature. We demonstrated that ultrasound-promoted condensation of 2-chlorobenzoic acid with aliphatic amines with the use of DMF as the solvent, especially in the case of secondary amines, affords products in high yields and reduces the reaction time to minutes. The results proved to be highly reproducible because the relevant sonochemical parameters were rigorously controlled. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Docampo, Maite L.,Pellon, Rolando F.,Estevez-Braun, Ana,Ravelo, Angel G.
p. 4111 - 4115
(2008/02/13)

HETEROCYCLIC COMPOUNDS THAT BLOCK THE EFFECTS OF ADVANCED GLYCATION END PRODUCTS (AGE)
The present invention relates to novel compounds of Formula (Ia) or (Ib), their pharmaceutically acceptable salts and pharmaceutically acceptable compositions containing them. Formula (Ia), or Formula (Ib) in the above formulae L represents Formula (I), Formula (II) or -(CH2)1- Q represents Formula (III), or Formula (IV). The present invention also relates to a process for the preparation of the above said novel compounds, their pharmaceutically acceptable salts and pharmaceutical compositions containing them. The present invention also relates to methods and compositions comprising compounds that treat pathophysiological conditions arising from inflammatory responses. In particular, the present invention is directed to compounds that inhibit or block glycated protein produced induction of the signaling-associated inflammatory responses in tissues, including endothelial cells. The present invention relates to compounds that inhibit smooth muscle proliferation. The present invention also relates to compounds that act as modulators of Perlecan activity and expression. In particular, the present invention is directed to compounds that inhibit smooth muscle cell proliferation by modulating heparan sulfate proteoglycans (HSPG) such as Perlecan. The present invention further relates to the use of compounds to treat vascular occlusive conditions characterized by smooth muscle proliferation such as stenosis, restenosis, neointimal hyperplasia, and atherosclerosis. The compounds of Formula (I) are also useful for the treatment and/or prevention of cancer. The types of cancers include melanoma, prostate, leukemia, lymphoma, non-small lung cancers, cancer of the central nervous system, breast, colon, ovarian or renal cancer.
-
Page/Page column 61

(2010/02/11)

Mono-N-methylation of functionalized anilines with alkyl methyl carbonates over NaY faujasites. 4. Kinetics and selectivity
(Chemical Equation Presented) In the presence of NaY faujasite as the catalyst, the reaction of bifunctional anilines (1-4: XC6H 4-NH2; X = OH, CO2H, CH2OH, and CONH2) with methyl alkyl carbonates [MeOCO2R′: R′ = Me or MeO(CH2)2O(CH2)2] proceeds with a very high mono-N-methyl selectivity (XC6H 4NHMe up to 99%), and chemoselectivity as well, with other nucleophilic functions (OH, CO2H, CH2OH, CONH2) fully preserved from alkylation and/or transesterification reactions. Aromatic substituents, however, modify the relative reactivity of amines 1-4: good evidence suggests that, not only steric and electronic effects, but, importantly, direct acid-base interactions between substituents and the catalyst are involved. Weakly acidic groups (OH, CH2OH, CONH2, pKa ≥ 10) may help the reaction, while aminobenzoic acids (pK a of 4-5) are the least reactive substrates. The solvent polarity also affects the reaction, which is faster in xylene than in the more polar diglyme. The mono-N-methyl selectivity is explained by the adsorption pattern of reagents within the zeolite pores: a BAl2 displacement of the amine on methyl alkyl carbonate should occur aided by the geometric features of the NaY supercavities. Different factors account for the reaction chemoselectivity. Evidence proves that the polarizability of the two nucleophilic terms (NH 2 and X groups) of anilines is relevant, although adsorption and confinement phenomena of reagents promoted by the zeolite should also be considered.
Selva, Maurizio,Tundo, Pietro,Foccardi, Tommaso
p. 2476 - 2485
(2007/10/03)

RNA structure analysis at single nucleotide resolution by Selective 2′-Hydroxyl Acylation and Primer Extension (SHAPE)
The reactivity of an RNA ribose hydroxyl is shown to be exquisitely sensitive to local nucleotide flexibility because a conformationally constrained adjacent 3′-phosphodiester inhibits formation of the deprotonated, nucleophilic oxyanion form of the 2′-hydroxyl group. Reaction with an appropriate electrophile, N-methylisatoic anhydride, to form a 2′-O-adduct thus can be used to monitor local structure at every nucleotide in an RNA. We develop a quantitative approach involving Selective 2′-Hydroxyl Acylation analyzed by Primer Extension (SHAPE) to map the structure of and to distinguish fine differences in structure for tRNAAsp transcripts at single nucleotide resolution. Modest extensions of the SHAPE approach will allow RNA structure to be monitored comprehensively and at single nucleotide resolution for RNAs of arbitrary sequence and structural complexity and under diverse solution environments.
Merino, Edward J.,Wilkinson, Kevin A.,Coughlan, Jennifer L.,Weeks, Kevin M.
p. 4223 - 4231
(2007/10/03)

Synthesis of mono-N-substituted functionalized anilines
The present invention relates to a process for direct and selective synthesis of mono-N-substituted functionalized anilines by using alkylating agents selected from the class of organic carbonates, preferably of the dialkyl, dibenzyl and diallyl types, in the presence of suitable catalysts that are chemically related to the class of aluminosilicates.
-
Page 4-5

(2008/06/13)

Synthesis of mono-N-substituted functionalized anilines
The present invention relates to a process for direct and selective synthesis of mono-N-substituted functionalized anilines by using alkylating agents selected from the class of organic carbonates, preferably of the dialkyl, dibenzyl and diallyl types, in the presence of suitable catalysts that are chemically related to the class of aluminosilicates.
-
Page 7

(2008/06/13)

Reaction of functionalized anilines with dimethyl carbonate over NaY faujasite. 3. Chemoselectivity toward mono-N-methylation
In the presence of NaY faujasite, dimethyl carbonate (MeOCO2Me, DMC) is a highly chemoselective methylating agent of functionalized anilines such as aminophenols (1), aminobenzyl alcohols (2), aminobenzoic acids (3), and aminobenzamides (4). The reaction proceeds with the exclusive formation of N-methylanilines without any concurrent O-methylation or N-/O-methoxy carbonylation side processes. Particularly, only mono-N-methyl derivatives [XC6H4NHMe, X = o-, m-, and p-OH; o- and p-CH 2OH; o- and P-CO2H; o- and p-CONH2] are obtained with selectivity up to 99% and isolated yields of 74-99%. DMC, which usually promotes methylations only at T > 120 °C, is activated by the zeolite catalyst and it reacts with compounds 1, 2, and 4, at 90 °C. Aminobenzoic acids (3) require a higher reaction temperature (≥130 °C).
Selva, Maurizio,Tundo, Pietro,Perosa, Alvise
p. 7374 - 7378
(2007/10/03)

The base-catalyzed oxygenation of quinoline derivatives
The base-catalyzed oxygenation of 1H-2-phenyl-3-hydroxy-4-oxoquinoline leads to cleavage products derived from either an endoperoxide or a 1,2-dioxetan intermediate. A persistent 1H-2-phenyl-3-oxy-4-oxoquinoline radical could also be detected by EPR in the reaction mixture.
Czaun, Miklós,Speier, Gábor
p. 5961 - 5963
(2007/10/03)

4-Hydroxy-2-quinolones. 37. Simple synthesis of 1-R-2-oxo-3,4-dihydroxyquinolines
3-Amino-1-R-2-oxo-4-hydroxyquinolines easily undergo acid hydrolysis with formation of the corresponding 1-R-2-oxo-3,4-dihydroxyquinolines. 1998 Plenum Publishing Corporation.
Ukrainets,Taran,Sidorenko,Gorokhova
p. 1334 - 1336
(2007/10/03)

Photochemistry of Pesticides, 10. Photodegradation of O,O-Diethyl-S(3,4-dihydro-4-oxobenzotriazin-3-yl-methyl)phosphorodithioate (Azinphos-ethyl)
The photodegradation of Azinphos-ethyl (1) in chloroform and methanol solution has been studied. 3,4-Dihydro-3-methyl-4-oxobenzotriazine (3), 3,4-dihydro-4-oxo-benzotriazine (5), O,O-diethyl-O(3-methylbenzotriazine-4-yl)phosphate (8), N-methylanthranilic acid (11) (in methanol: methyl ester 12), and sulfur have been isolated and characterized as photoproducts.The decay mechanism is discussed. - Azinphos Ethyl, Photodegradation, 4-Oxobenzotriazines, O-Phosphates, N-Methyl-anthranilic Acid
Abdou, W. M.,Sidky, M. M.,Wamhoff, H.
p. 907 - 910
(2007/10/02)

Carbon Dioxide: A Reagent for the Simultaneous Protection of Nucleophilic Centres and the Activation of Alternative Locations to Electrophilic Attack. Prt III. A New Synthetic Method for the ortho-Substitution of N-Monoalkylanilines
N-Methyl- and N-ethyl-aniline are regiospecifically converted into a range of ortho-substituted derivatives, using carbon dioxide both for N-protection and as an intermediate carbanion stabilizing group, and t-butyllithium to lithiate the ortho-carbon atom.The rersulting lithium N-(ortho-substituted-phenyl)-N-methyl- and -N-ethylcarbamates undergo smooth acid-catalysed decarboxylation under mild conditions.No alpha-substituted products were detected.
Katritzky, Alan R.,Fan, Wei-Qiang,Akutagawa, Kunihiko
p. 4027 - 4034
(2007/10/02)

Protease inhibitors
This invention relates to methods of preventing or reducing the degradation of elastin and other proteins and thereby preventing or retarding the disease states caused by said degradation by administering compounds, some of which are novel, of the formula: STR1 or their pharmacologically acceptable salts.
-
(2008/06/13)

Conformational Behaviour of Medium-sized Rings. Part 11. Dianthranilides and Trianthranilides
Two approaches to the stepwise syntheses of N,N'-di- and N,N',N''-tri-substituted trianthranilide derivatives (5)-(20) are described.In the shorter synthetic route, the key acyclic intermediate, N-anthranilic acid (26) is prepared in a stepwise manner from anthranilic acid, isatoic anhydride (23), followed by o-nitrobenzoyl chloride.Alkylations of the amide functions at nitrogen, reductions of the aromatic nitrogroups, and cyclisations of the acyclic amino-acid derivatives provide a direct route to N,N'-dimethyl- (5) and N,N'-dibenzyl- (14) trianthranilides.Further alkylations or acylations of either (5) or (14) afford (i) N,N',N''-trimethyltrianthranilide (7) and its trideuteriomethyl analogue (8), (ii) N,N'-dimethyl-N''-acetyl- (10), -N''-benzoyl- (11), and -N''-benzyl- (12) trianthranilides, (iii) N,N',N''-tribenzyltrianthranilide (15), and (iv) N,N'-dibenzyl-N''-methyltrianthranilide (16).In the longer synthetic route, the key acyclic intermediate, methyl N-methyl-N-anthranilate (42) is prepared in a stepwise manner from anthranilic acid and two molar equivalents of o-nitrobenzoyl chloride.Alkylations of the unsubstituted amide functions at nitrogen, reductions of the aromatic nitro-groups, and cyclisations of the acyclic amino-acid derivatives provide, not only an alternative route to N,N'-dimethyltrianthranilide (5) but also, a general route to the N-methyl-N'-trideuteriomethyl- (6), N-methyl-N'-benzyl- (17), and N-methyl-N'-ethyl- (19) analogues.Further alkylations of these N,N'-disubstituted derivatives afford N-methyl-N',N''-di(trideuteriomethyl)- (9), N-methyl-N'-trideuteriomethyl-N''-benzyl- (13), N-methyl-N'-benzyl-N''-ethyl- (18), and N-methyl-N'-ethyl-N''-benzyl- (20) trianthranilides.The constitutionally symmetrical N,N',N''-trimethyl- (7) and N,N',N''-tribenzyl- (15) trianthranilides exist in solution as an equilibrium mixture of propeller and helical conformations.In the case of the N,N',N''-trimethyl derivative (7), the predominant diastereoisomer with the helical conformation has been isolated as a pure compound.In the case of the N,N',N''-tribenzyl derivative (15), the propeller and helical conformational diastereoisomers have both been characterised as crystalline compounds.For both these compounds, the free-energy barriers to conformational inversion and interconversion processes in solution have been obtained from (i) direct equilibration experiments and (ii) dynamic 1H n.m.r. spectroscopy.Constitutionally unsymmetrical N,N'-di- and N,N',N''-tri-substituted trianthranilide derivatives can adopt three helical conformations in addition to a propeller conformation.Assignments have been made to conformations and conformational diastereoisomers of the N,N'-dimethyl- (5), N,N'-dimethyl-N''-benzyl- (12), N,N'-dibenzyl- (14), N,N'-dibenzyl-N''-methyl- (16), N-methyl-N'-benzyl- (17), N-methyl-N'-benzyl-N''-ethyl- ...
Hoorfar, Alireza,Ollis, W. David,Price, Jennifer A.,Stephanatou, Julia Stephanidou,Stoddart, J. Fraser
p. 1649 - 1700
(2007/10/02)

Ethyl Carbamate as an Aminocarbonylating Agent: Modification of Gattermann's Amidation Reaction
-
Chakraborty, D. P.,Mandal, Anchal Kanti,Roy, Swapan Kumar
p. 977 - 979
(2007/10/02)

New Olefin and Oxiran Syntheses from Carbonyl Compounds, and Diethyl Sodiophosphonate Anions and 1-Aminophosphonate Amino-anions
Reaction of aromatic aldehydes, and phthalic and thiophthalic anhydrides, with diethyl sodiophosphonate (1) gives the trans-stilbenes (3), 3,3'-biphthalidylidene (30), and 3,3'-bis-(2-thiophthalidylidene) (33).Similar treatment of fluorenone (8) and xanthone (17) with (1) leads to 9,9'-bis(fluororenylidene) (9) and 9,10-dihydro-9-oxophenanthrene-10-spiro-9'-fluorene (10), and to 9,9'-bixanthenylidene (18) and 9,9'-bixanthenyl (19), respectively, but the reaction using anthrone (11) as a carbonyl reagent yields only anthraquinone (12) and anthracene (13).Similar treatment using N-methylisatoic anhydride (34) and N-methylisatin (36) produces NN'-dimethylisoindigo (35).Reaction of benzaldehyde and p-chlorobenzaldehyde with diethyl 1--cyclohexylphosphonate (40) gives mainly corresponding mixtures of trans- (41a,b) and cis-stilbene epoxides (42a,b), while similar treatment of p-nitrobenzaldehyde with (40) produces 4,4'-dinitrostilbene (3e).Reaction of (8) with (40), as well as with (1), gives (9) and (10).The mechanism of formation of these products is discussed.
Minami, Toru,Matsuzaki, Narihide,Ohshiro, Yoshiki,Agawa, Toshio
p. 1731 - 1738
(2007/10/02)

The Chemistry of 2H-1,3-Benzoxazine-2,4-(1H)dione (Isatoic Anhydride). 8. A One Step Synthesis of the Quinindoline Ring System and Related Compounds
The reaction between N-substituted isatoic anhydrides and the carbanion generated from 3-methylthiooxindole to produce the quinindoline ring skeleton is discussed.Analogous reactions of azaisatoic anhydride 6 and tricyclic anhydride 8 produces the 4-aza analog 7 and pentacycle 9.Some spectral data is also described.
Coppola, Gary M.
p. 1785 - 1787
(2007/10/02)