103-67-3Relevant articles and documents
Solid-phase synthesis of tertiary N-Methyl amines including tropanes
Sienkiewicz, Michal,Lazny, Ryszard
, p. 5 - 8 (2010)
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Mechanism of α-Amino Acids decomposition in the gas phase. Experimental and theoretical study of the elimination kinetics of N-Benzyl Glycine Ethyl Ester
Tosta, Maria,Oliveros, Jhenny C.,Mora, Jose R.,Cordova, Tania,Chuchani, Gabriel
, p. 2483 - 2488 (2010)
The gas-phase elimination kinetics of N-benzylglycine ethyl ester was examined in a static system, seasoned with allyl bromide, and in the presence of the free chain radical suppressor toluene. The working temperature and pressure range were 386.4-426.7 °C and 16.7-40.0 torr, respectively. The reaction showed to be homogeneous, unimolecular, and obeys a first-order rate law. The elimination products are benzylglycine and ethylene. However, the intermediate benzylglycine is unstable under the reaction conditions decomposing into benzyl methylamine and CO2 gas. The variation of the rate coefficients with temperature is expressed by the following Arrhenius equation: log k1 (s-1) = (11.83 ± 0.52) - (190.3 ± 6.9) kJ mol -1 (2.303RT)-1. The theoretical calculation of the kinetic parameters and mechanism of elimination of this ester were performed at B3LYP/6-31G*, B3LYP/6-31+G**, MPW1PW91/6-31G*, and MPW1PW91/6-31+G** levels of theory. The calculation results suggest a molecular mechanism of a concerted nonsynchronous six-membered cyclic transition state process. The analysis of bond order and natural bond orbital charges implies that the bond polarization of C(=O)O-C, in the sense of C(=O)Oδ-...Cδ+, is rate determining. The experimental and theoretical parameters have been found to be in reasonable agreement.
New catalyst systems for iron-catalyzed hydrosilane reduction of carboxamides
Tsutsumi, Hironori,Sunada, Yusuke,Nagashima, Hideo
, p. 6581 - 6583 (2011)
A heptanuclear iron carbonyl cluster, [Fe3(CO) 11(μ-H)]2Fe(DMF)4 (4), is found to be a highly efficient catalyst for the reduction of various carboxamides by 1,2-bis(dimethylsilyl)benzene (BDSB), which makes possible reducing the amount of the catalyst, shortening the reaction time, and lowering the reaction temperatures.
Simultaneous Deprotection and Purification of BOC-amines Based on Ionic Resin Capture
Liu, Yun-Shan,Zhao, Cunxiang,Bergbreiter, David E.,Romo, Daniel
, p. 3471 - 3473 (1998)
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Reactions of N-Halobenzylalkylamines with Sodium Methoxide in Methanol
Cho, Bong Rae,Yoon, Jong Chan,Bartsch, Richard A.
, p. 4943 - 4946 (1985)
Reactions of N-halobenzylmethylamines 1 and 2 (X = Cl and Br) with MeONa-MeOH have been investigated.Eliminations from 1 were quantitative, producing only benzylidenemethylamines.Reaction of 2 with MeONa-MeOH produced benzylidenemethylamines and benzylmethylamines.The yield of benzylidenemethylamine increased with electron-withdrawing aryl substituents and increased base concentration and became quantitative when pentane was used as a solvent.The results are interpreted as competing bimolecular elimination and nucleophilic substitution by methoxide on bromine.Product studies for reaction of N-halobenzyl-tert-butylamines with MeONa-MeOH and EtSNa-MeOH establish that the substitution reaction is a general reaction pathway available for the N-haloamines.Transition states for eliminations from 1 and 2 are characterized by Hammett ρ and primary deuterium isotope effect values.
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Noller,Kneeland
, p. 201 (1946)
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Reduction of amides with NaBH4 in diglyme at 162°C
Zhu, Hua-Jie,Lu, Kai-Tao,Sun, Guang-Ri,He, Jin-Bao,Li, Hai-Qing,Pittman Jr., Charles U.
, p. 409 - 413 (2003)
High temperature (162°C) reductions of aromatic amides were studied to extend the useful range of functional group transformations by NaBH4. Primary aromatic amides were reduced to the amines with NaBH4-diglyme at 162°C. Reduction proceeds via fast initial loss of hydrogen, followed by formation of the corresponding nitrile, which is then more slowly reduced to the amine. N-Methylbenzamide is not reduced under these conditions, but it is reduced to benzylmethylamine when LiCl is added to NaBH4-diglyme at 162°C. LiCl addition raised the rate of primary aromatic amide and aromatic nitrile conversions to both the nitrile, first, and the amine. An intermediate was isolated from the reaction of N-benzylformamide with NaBH4-LiCl in diglyme at 162°C. It was examined by 1H NMR, atomic absorption, IR and thermal decomposition. Possible structures are proposed. A mechanism for the reduction of primary aromatic amides is proposed based on the initial evolution of one mole equivalent of hydrogen and formation of the nitrile prior to further reduction to amine.
Chelating bis-carbene rhodium(III) complexes in transfer hydrogenation of ketones and imines
Albrecht, Martin,Crabtree, Robert H.,Mata, Jose,Peris, Eduardo
, p. 32 - 33 (2002)
Chelating rhodium(III) carbene complexes are accessible via a simple synthesis and are catalytically active for hydrogen transfer from alcohols to ketones and imines.
Deprotection of o-nitrobenzensulfonyl (nosyl) derivatives of amines mediated by a solid-supported thiol
Cardullo, Francesca,Donati, Daniele,Merlo, Giancarlo,Paio, Alfredo,Salaris, Margherita,Taddei, Maurizio
, p. 2996 - 2998 (2005)
A new protocol based on a solid-supported thiol was developed for high yielding deprotection of o-nitrobenzensulfonyl amides derived from primary and secondary amines. The reaction can be carried out at room temperature for 24 hours or accelerated by microwave irradiation, going to completion in six minutes. Georg Thieme Verlag Stuttgart.
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Abatjoglou,A.G.,Eliel,E.L.
, p. 3042 - 3043 (1974)
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The reaction of benzothiazole sulfenamide with (TMS)3SiH: An example of degenerate-branched chain process
Varlamov, Vladimir T.,Ferreri, Carla,Chatgilialoglu, Chryssostomos
, p. 1756 - 1762 (2005)
The reaction of sulfenamide 3 with (TMS)3SiH initiated by the decomposition of AIBN at 76°C has been studied in some detail. The reaction is a rare example of a radical chain-branching process. The two main products are dialkylamine 4 and the thiosilane 5. It is also established that 2-mercaptobenzothiazole (2) is formed in a substantial yield as one of the by-products. The mechanism of this chain autocatalytic reaction is complex due to a mix of different radical chain reactions and some discussion is provided. The amine obtained in a quantitative yield can arise from two independent routes of attack of (TMS)3Si. radical on sulfenamide 3. The minor route affords thiol 2 that can act as a catalyst for the major route during the reaction course and then gives a salt with secondary amine, which precipitates upon cooling. The origin of autocatalysis is discussed in some detail.
Electrolytic N-Alkylation of Amines with Alcohols
Ohtani, Bunsho,Nakagawa, Koji,Nishimoto, Sei-ichi,Kagiya, Tsutomu
, p. 1917 - 1920 (1986)
Electrolysis of the alcohol solution of amines in a one-chamber cell resulted in N-alkylation of the amines with sufficient current efficiencies.Platinum black particles suspended in the reaction mixture enhanced the efficiency due to their catalytic role for hydrogenation of a Schiff base intermediate.
Carbamate linkers as latent N-methylamines in solid phase synthesis
Ho, Chih Y.,Kukla, Michael J.
, p. 2799 - 2802 (1997)
A new linker strategy for solid phase synthesis has been developed. It utilizes LAH reduction of a carbamate connection to Wang resin which results in N-methylamines, a useful functionality in medicinal chemistry.
Design, synthesis, and biological evaluation of a series of resorcinol-based N-benzyl benzamide derivatives as potent Hsp90 inhibitors
Park, Sun You,Oh, Yong Jin,Lho, Yunmee,Jeong, Ju Hui,Liu, Kwang-Hyeon,Song, Jaeyoung,Kim, Soong-Hyun,Ha, Eunyoung,Seo, Young Ho
, p. 390 - 401 (2018)
Heat shock protein 90 (Hsp90) is a ubiquitous molecular chaperone that is responsible for the stabilization and maturation of many oncogenic proteins. Therefore, Hsp90 has emerged as an attractive target in the field of cancer chemotherapy. In this study, we report the design, synthesis, and biological evaluation of a series of Hsp90 inhibitors. In particular, compound 30f shows a significant Hsp90α inhibitory activity with IC50 value of 5.3 nM and an excellent growth inhibition with GI50 value of 0.42 μM against non-small cell lung cancer cells, H1975. Compound 30f effectively reduces the expression levels of Hsp90 client proteins including Her2, EGFR, Met, Akt, and c-Raf. Consequently, compound 30f promotes substantial cleavages of PARP, Caspase 3, and Caspase 8, indicating that 30f induces cancer cell death via apoptotic pathway. Moreover, cytochrome P450 assay indicates that compound 30f has weak inhibitory effect on the activities of five major P450 isoforms (IC50 > 5 μM for 1A2, 2C9, 2C19, 2D6, and 3A), suggesting that clinical interactions between 30f and the substrate drugs of the five major P450 isoforms are not expected. Compound 30f also inhibits the tumor growth in a mouse xenograft model bearing subcutaneous H1975 without noticeable abnormal behavior and body weight changes. The immunostaining and western immunoblot analysis of EGFR, Met, Akt in xenograft tissue sections of tumor further demonstrate a good agreement with the in vitro results.
Naphthalene-catalysed lithiation of phenone imines in the presence of carbonyl compounds: Preparation of 1,2-aminoalcohols
Guijarro, David,Yus, Miguel
, p. 7761 - 7768 (1993)
The lithiation of different phenone imines 1 with an excess of lithium powder and a catalytic amount (8 mol %) of naphthalene in the presence of several carbonyl compounds 2 in tetrahydrofuran at temperatures ranging between -78 and 20°C leads, after hydrolysis with water, to the corresponding 1,2-aminoalcohols 3 in moderate yields.
A Convenient and Stable Heterogeneous Nickel Catalyst for Hydrodehalogenation of Aryl Halides Using Molecular Hydrogen
Anwar, Muhammad,Beller, Matthias,Dastgir, Sarim,Junge, Kathrin,Leonard, David K.,Ryabchuk, Pavel
, (2022/02/03)
Hydrodehalogenation is an effective strategy for transforming persistent and potentially toxic organohalides into their more benign congeners. Common methods utilize Pd/C or Raney-nickel as catalysts, which are either expensive or have safety concerns. In this study, a nickel-based catalyst supported on titania (Ni-phen@TiO2-800) is used as a safe alternative to pyrophoric Raney-nickel. The catalyst is prepared in a straightforward fashion by deposition of nickel(II)/1,10-phenanthroline on titania, followed by pyrolysis. The catalytic material, which was characterized by SEM, TEM, XRD, and XPS, consists of nickel nanoparticles covered with N-doped carbon layers. By using design of experiments (DoE), this nanostructured catalyst is found to be proficient for the facile and selective hydrodehalogenation of a diverse range of substrates bearing C?I, C?Br, or C?Cl bonds (>30 examples). The practicality of this catalyst system is demonstrated by the dehalogenation of environmentally hazardous and polyhalogenated substrates atrazine, tetrabromobisphenol A, tetrachlorobenzene, and a polybrominated diphenyl ether (PBDE).
Design, Synthesis, and Biological Evaluation of Novel 3-Aminomethylindole Derivatives as Potential Multifunctional Anti-Inflammatory and Neurotrophic Agents
Wang, Wei-Wei,Liu, Ting,Lv, Yu-Meng,Zhang, Wu-Yang,Liu, Zhi-Gang,Gao, Jin-Ming,Li, Ding
, p. 1593 - 1605 (2021/05/31)
The development of multifunctional molecules that are able to simultaneously interact with several pathological components has been considered as a solution to treat the complex pathologies of neurodegenerative diseases. Herein, a series of aminomethylindole derivatives were synthesized, and evaluation of their application for antineuroinflammation and promoting neurite outgrowth was disclosed. Our initial screening showed that most of the compounds potently inhibited lipopolysaccharide (LPS)-stimulated production of NO in microglial cells and potentiated the action of NGF to promote neurite outgrowth of PC12 cells. Interestingly, with outstanding NO/TNF-α production inhibition and neurite outgrowth-promoting activities, compounds 8c and 8g were capable of rescuing cells after injury by H2O2. Their antineuroinflammatory effects were associated with the downregulation of the LPS-induced expression of the inflammatory mediators inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). Western blotting and immunofluorescence assay results indicated that the mechanism of their antineuroinflammatory actions involved suppression of the MAPK/NF-κB signal pathways. Further studies revealed that another important reason for the high comprehensive antineuroinflammatory activity was the anti-COX-2 capabilities of the compounds. All these results suggest that the potential biochemical multifunctional profiles of the aminomethylindole derivatives provide a new sight for the treatment of neurodegenerative diseases.
