- Synthesis, Pharmacological Characterization, and Structure-Activity Relationships of Noncanonical Selective Agonists for α7 nAChRs
-
A lack of selectivity of classical agonists for the nicotinic acetylcholine receptors (nAChR) has prompted us to identify and develop a distinct scaffold of α7 nAChR-selective ligands. Noncanonical 2,4,6-substituted pyrimidine analogues were framed around compound 40 for a structure-activity relationship study. The new lead compounds activate selectively the α7 nAChRs with EC50's between 30 and 140 nM in a PNU-120596-dependent, cell-based calcium influx assay. After characterizing the expanded lead landscape, we ranked the compounds for rapid activation using Xenopus oocytes expressing human α7 nAChR with a two-electrode voltage clamp. This approach enabled us to define the molecular determinants governing rapid activation, agonist potency, and desensitization of α7 nAChRs after exposure to pyrimidine analogues, thereby distinguishing this subclass of noncanonical agonists from previously defined types of agonists (agonists, partial agonists, silent agonists, and ago-PAMs). By NMR, we analyzed pKa values for ionization of lead candidates, demonstrating distinctive modes of interaction for this landscape of ligands.
- Camacho-Hernandez, Gisela Andrea,Stokes, Clare,Duggan, Brendan M.,Kaczanowska, Katarzyna,Brandao-Araiza, Stefania,Doan, Lisa,Papke, Roger L.,Taylor, Palmer
-
-
Read Online
- NADH MODEL REDUCTION: BIOMIMETIC SYNTHESIS OF α-AMINO ACIDS FROM α-KETO ACIDS
-
Protonated α-imino acids, RC(=NH2+)COOH, were easily reduced to α-amino acids by an acid-stable NADH analoque, 1-benzyl-3-carbamoyl-1,4-dihydroquinoline.This is the first model reaction of NADH-mediated α-amino acid synthesis from α-keto acids.
- Shinkai, Seiji,Hamada, Hisatake,Dohyama, Akihiko,Manabe, Osamu
-
-
Read Online
- Activity-Based Sensing of Ascorbate by Using Copper-Mediated Oxidative Bond Cleavage
-
Ascorbate is an important biological reductant and enzyme cofactor. Although direct detection through ascorbate-mediated reduction is possible, this approach suffers from poor selectivity due to the wide range of cellular reducing agents. To overcome this limitation, we leverage reduction potential of ascorbate to mediate a copper-mediated oxidative bond cleavage of ether-caged fluorophores. The copper(II) complexes supported by a {bis(2-pyridylmethyl)}benzylamine or a {bis(2-pyridylmethyl)}(2-methoxybenzyl)amine ligand were identified as an ascorbate responsive unit and their reaction with ascorbate yields a copper-based oxidant that enables rapid benzylic oxidation and the release of an ether-caged dye (coumarin or fluorescein). The copper-mediated bond cleavage is specific to ascorbate and the trigger can be readily derivatized for tuning photophysical properties of the probes. The probes were successfully applied for the fluorometric detection of ascorbate in commercial food samples, human plasma, and serum, and within live cells by using confocal microscopy and flow cytometry.
- Yu, Zuo Hang,Reinhardt, Christopher J.,Wong, Thomas Hin-Fung,Tong, Ka Yan,Chan, Jefferson,Au-Yeung, Ho Yu
-
-
Read Online
- Syntheses and chromotropic behavior of two halo bridged dinuclear copper(II) complexes containing pyridine-based bidentate ligand
-
Two dinuclear doubly bridged copper(II) complexes [LCu(μ-Cl)Cl]2 (1) and [LCu(μ-Br)Br]2 (2), where L represents N-benzyl(pyridine-2-yl)methaneamine, have been synthesized to investigate their chromotropic behavior. The structures of the complexes were characterized by elemental analyses, various spectroscopic techniques (IR, UV–Vis, and EPR), molar conductance measurements and thermal analysis. The crystal structure of compound 1 indicated both copper(II) centers are located in N2Cl3 environments with distorted square pyramidal geometries, which sharing one base to apex edge. The complexes are chromotropic and their solvatochromism, halochromism, and thermochromism properties were investigated by visible absorption spectroscopy. The solvatochromic properties of the complexes are attributed to structural changes in various solvents. Their halochromism phenomena arise from protonation and deprotonation of coordinated ligands in the pH range of 2.0–10.5, and the reversible thermochromism in DMF and DMSO solutions is triggered by replacing the ligands by solvent molecules.
- Shirvan, Atie,Golchoubian, Hamid,Bouwman, Elisabeth
-
-
Read Online
- Calix[4]arenes Linked to Multiple Bidentate N-Donors: Potential Ligands for Synthetic Modeling of Multinuclear Metalloenzymes
-
(Matrix Presented) A series of calix[4]arenes incorporating three or four bidentate diamines or pyridylamines attached at the upper rim were synthesized via practical protocols. Proof of structure was obtained in one instance by X-ray crystallography. These molecules are designed for general use as ligands for the preparation of multinuclear active site models of metalloenzymes.
- Spencer, Douglas J. E.,Johnson, Bryan J.,Johnson, Brian J.,Tolman, William B.
-
-
Read Online
- Nickel Complexes Bearing N,N,O-Tridentate Salicylaldiminato Ligand: Efficient Catalysts for Imines Formation via Dehydrogenative Coupling of Primary Alcohols with Amines
-
Treatment of salicylaldiminato ligand L1H-L2H (L1H = 2,4-di-tert-butyl-6-((quinolin-8-ylimino)methyl)phenol; L2H = 2,4-di-tert-butyl-6-(((2-(diethylamino)ethyl)imino)methyl)phenol) with Ni(OAc)2·4H2O in refluxing ethanol afforded nickel complexes [(L1)Ni(OAc)] (1) and [(L2)Ni(OAc)] (2), respectively. Reaction of L3H (L3H = (2,4-di-tert-butyl-6-(((2-(pyridin-2-yl)ethyl)imino)methyl)phenol)) with Ni(OAc)2·4H2O in the presence of excess triethylanmine gave the dual ligands coordinated nickel complex [(L2)2Ni] (3). Complexes 1-3 were well characterized by high-resolution mass spectrometry, infrared spectroscopy, elemental analysis, and X-ray diffraction analysis. All the three Ni(II) complexes exhibited efficient activity and good selectivity in the acceptorless dehydrogenative coupling of alcohols and amines to produce imines and diimines. The present protocol provides an atom-economical and sustainable route for the synthesis of various imine derivatives by employing an earth-abundant nickel salt and easily prepared salicylaldiminato ligands.
- Han, Zhangang,Hao, Zhiqiang,Lin, Jin,Lu, Guo-Liang,Zhang, Junhua,Zhang, Xiaoying
-
p. 3843 - 3853
(2021/11/18)
-
- Phosphine-Free Manganese Catalyst Enables Selective Transfer Hydrogenation of Nitriles to Primary and Secondary Amines Using Ammonia-Borane
-
Herein we report the synthesis of primary and secondary amines by nitrile hydrogenation, employing a borrowing hydrogenation strategy. A class of phosphine-free manganese(I) complexes bearing sulfur side arms catalyzed the reaction under mild reaction conditions, where ammonia-borane is used as the source of hydrogen. The synthetic protocol is chemodivergent, as the final product is either primary or secondary amine, which can be controlled by changing the catalyst structure and the polarity of the reaction medium. The significant advantage of this method is that the protocol operates without externally added base or other additives as well as obviates the use of high-pressure dihydrogen gas required for other nitrile hydrogenation reactions. Utilizing this method, a wide variety of primary and symmetric and asymmetric secondary amines were synthesized in high yields. A mechanistic study involving kinetic experiments and high-level DFT computations revealed that both outer-sphere dehydrogenation and inner-sphere hydrogenation were predominantly operative in the catalytic cycle.
- Sarkar, Koushik,Das, Kuhali,Kundu, Abhishek,Adhikari, Debashis,Maji, Biplab
-
p. 2786 - 2794
(2021/03/03)
-
- Synthesis and characterization of N,N-chelate manganese complexes and applications in C[sbnd]N coupling reactions
-
Bidentate NN-ligands have been derived from the reaction between aldehydes and 2-(aminomethyl)pyridine. The treatment of these ligands with Mn(CO)5Br gave complexes that are highly bench stable. The complexes were characterized by various analytical and spectral methods. Single-crystal XRD of complex Mn-2 was performed, which indicates an octahedral geometry around the metal center. The complexes efficiently catalyze the N-alkylation of anilines with alcohols under optimized reaction conditions.
- Das, Kuhali,Kumar, Amol,Jana, Akash,Maji, Biplab
-
-
- Ru(II) complexes containing (2-(pyren-1-ylmethylene)hydrazinyl)benzothiazole: Synthesis, solid-state structure, computational study and catalysis in N-alkylation reactions
-
Reactions of (2-(pyren-1-ylmethylene)hydrazinyl)benzothiazole (L) with ruthenium(II) prefabricated precursors [RuHCl(CO)(EPh3)3] and [RuH2(CO)(EPh3)3] (E = P or As) afforded new Ru(II) complexes [RuCl(CO)(EPh3)2(L)] and [RuH(CO)(EPh3)2(L)] (E = P or As) (1–4). All the Ru(II) complexes (1–4) were characterized by IR, NMR spectroscopies, ESI-mass spectrometry and elemental analyses. The solid-state structures of Ru(II) complexes (2 and 3) were established by single crystal X-ray analyses and revealed distorted octahedral geometries around the ruthenium(II) ion and mono anionic bidentate N^N coordination mode for hydrazine ligand. The Ru(II) complexes 2 and 3 were also analyzed using Hirshfeld surface analysis and DFT calculations. Moreover, all the complexes (1–4) were utilized in the N-alkylation reactions of amines using alcohol. Complex 3 was found to be highly active towards N-alkylation of different aromatic amines with alcohol.
- Murugan, Kaliyappan,Ojwach, Stephen O.,Saravanan, Kandasamy,Vijayan, Paranthaman,Vijayapritha, Subbarayan,Viswanathamurthi, Periasamy
-
-
- Zn148 is a modular synthetic metallo-β-lactamase inhibitor that reverses carbapenem resistance in Gram-negative pathogens in vivo
-
Carbapenem-resistant Gram-negative pathogens are a critical public health threat and there is an urgent need for new treatments. Carbapenemases (β- lactamases able to inactivate carbapenems) have been identified in both serine β-lactamase (SBL) and metallo-β-lactamase (MBL) families. The recent introduction of SBL carbapenemase inhibitors has provided alternative therapeutic options. Unfortunately, there are no approved inhibitors of MBL-mediated carbapenem-resistance and treatment options for infections caused by MBL-producing Gram-negatives are limited. Here, we present ZN148, a zinc-chelating MBL-inhibitor capable of restoring the bactericidal effect of meropenem and in vitro clinical susceptibility to carbapenems in >98percent of a large international collection of MBL-producing clinical Enterobacterales strains (n = 234). Moreover, ZN148 was able to potentiate the effect of meropenem against NDM-1-producing Klebsiella pneumoniae in a murine neutropenic peritonitis model. ZN148 showed no inhibition of the human zinc-containing enzyme glyoxylase II at 500 μM, and no acute toxicity was observed in an in vivo mouse model with cumulative dosages up to 128 mg/kg. Biochemical analysis showed a time-dependent inhibition of MBLs by ZN148 and removal of zinc ions from the active site. Addition of exogenous zinc after ZN148 exposure only restored MBL activity by -30percent, suggesting an irreversible mechanism of inhibition. Mass-spectrometry and molecular modeling indicated potential oxidation of the active site Cys221 residue. Overall, these results demonstrate the therapeutic potential of a ZN148-carbapenem combination against MBL-producing Gram-negative pathogens and that ZN148 is a highly promising MBL inhibitor that is capable of operating in a functional space not presently filled by any clinically approved compound.
- Andresen, Adriana Magalhaes Santos,Bayer, Annette,Carlsen, Trine Josefine Olsen,Finke, Sarah,Heikal, Adam,Huber, Sandra,Kildahl-Andersen, Geir,Lauksund, Silje,Leiros, Hanna-Kirsti S.,Schnaars, Christian,Skagseth, Susann,?strand, Ove Alexander H?gmoen,?kstad, Ole Andreas,Fr?hlich, Christopher,Gj?en, Tor,Rongved, P?l,Samuelsen, ?rjan
-
supporting information
(2020/06/02)
-
- Compound capable of being strongly bound with alpha-synuclein aggregate, and preparation method and use of compound
-
The invention belongs to the technical field of medicine, and relates to a compound with a structural general formula I, and a preparation method and use of the compound. In the formula I, R1 is selected from phenyl, substituted phenyl, pyridyl and pyrimidinyl, and i is selected from 0 to 2, and is an integer; R2 is selected from alkyl, phenyl, substituted phenyl and 5-6-membered aromatic heterocyclic rings, and m is selected from 0 to 5, and is an integer; and R3 is selected from phenyl and substituted phenyl, and n is selected from 0 to 3, and is an integer. The compound comprises a cis-isomer, a trans-isomer or a mixture of the cis-isomer and the trans-isomer of the compound with the formula I structure. The compound can be strongly bound to an alpha-synuclein aggregate, can be used asan imaging tracer for the image technology such as PET, SPECT and the like, or can be used for preparing an imaging tracer and a composition containing the imaging tracer, the compound can be used forparticularly detecting Parkinson's disease or neurological disorders associated with the misfolding and aggregation of alpha-synuclein, and the compound has very good application prospects.
- -
-
Paragraph 0027; 0029-0031; 0141-0143
(2019/08/30)
-
- Synthesis and characterization of aminopyridine iron(ii) chloride catalysts for isoprene polymerization: Sterically controlled monomer enchainment
-
In this study, a series of 2-R-6-(1-(alkylamino)methyl)pyridine-iron complexes [alkyl: (CPh3) Fe1H; (CHPh2) Fe2H; (CHPh2) Fe3Me; (CHMePh) Fe4H; (CH2Ph) Fe5H; (CHMe2) Fe6H; (C6H11) Fe7H; (CH2(4-OMe)Ph) Fe8H; (CH2(4-CF3)Ph) Fe9H; (CH2(2,4,6-Me3)Ph) Fe10H; (CH2Ph) Fe11Me] were synthesized and well characterized by ATR-IR spectroscopy, HRMS spectroscopy and elemental analysis. In addition, Fe3Me, Fe4H, Fe7H and Fe11Me were characterized by X-ray diffraction analysis: Fe3Me and Fe11Me adopted distorted tetrahedral geometries in the solid state while Fe4H and Fe7H were found in dimeric or polymeric forms respectively in which chlorides acted as bridging ligands. The catalytic capacities of these iron complexes were investigated for isoprene polymerization. Upon activation with a MAO cocatalyst, the catalytic activities of complexes varied as a function of the steric and electronic influences of substituents. In general, the catalysts bearing the least steric groups and electron-withdrawing groups exhibited relatively high activities. An outstanding activity of 190.6 × 104 g·mol-1·h-1 was obtained by Fe5H [CH2Ph]. Moreover, changes in the steric hindrance around the metal center showed a notable effect on the selectivity of monomer enchainment. In particular, most of the polymers obtained by these complexes bearing flexible frameworks were in favor of 3,4-enchainment.
- Jing, Chuyang,Wang, Liang,Mahmood, Qaiser,Zhao, Mengmeng,Zhu, Guangqian,Zhang, Xianhui,Wang, Xiaowu,Wang, Qinggang
-
p. 7862 - 7874
(2019/06/13)
-
- Improving C=N bond reductions with (Cyclopentadienone)iron complexes: Scope and limitations
-
Herein, we broaden the application scope of (cyclo-pentadienone)iron complexes 1 in C=N bond reduction. The catalytic scope of pre-catalyst 1b, which is more active than the “Kn?lker complex” (1a) and other members of its family, has been expanded to the catalytic transfer hydrogenation (CTH) of a wider range of aldimines and ketimines, either pre-isolated or generated in situ. The kinetics of 1b-promoted CTH of ketimine S1 were assessed, showing a pseudo-first order profile, with TOF = 6.07 h–1 at 50 % conversion. Moreover, the chiral complex 1c and its analog 1d were employed in the enantioselective reduction of ketimines and reductive amination of ketones, giving fair to good yields and moderate enantioselectivity.
- Cettolin, Mattia,Bai, Xishan,Lübken, Dennis,Gatti, Marco,Facchini, Sofia Vailati,Piarulli, Umberto,Pignataro, Luca,Gennari, Cesare
-
p. 647 - 654
(2018/10/24)
-
- Cyclopentadienyl-Ru(II)-Pyridylamine Complexes: Synthesis, X-ray Structure, and Application in Catalytic Transformation of Bio-Derived Furans to Levulinic Acid and Diketones in Water
-
A series of cationic half-sandwich cyclopentadienyl-ruthenium(II)-pyridylamine complexes, [(η5-C5H5)Ru(κ2-L)(PPh3)]+ (L = Namine-substituted pyridylamine ligands) ([Ru]-1-[Ru]-6), along with the analogous cyclopentadienyl-ruthenium(II)-N-isopropylpyridylimine complex [(η5-C5H5)Ru(κ2-L)(PPh3)]+ (L = N-isopropylpyridylimine) ([Ru]-7), have been synthesized in good yields. Structural identities of all the complexes have been authenticated by 1H, 13C, and 31P NMR, mass spectrometry, and X-ray crystallography. The synthesized complexes exhibited high catalytic activity for the transformation of the bio-derived furans, 2-furfural (furfural), 5-methyl-2-furfural (5-MF), and 5-hydroxymethyl-2-furfural (5-HMF) to levulinic acid (LA) and the diketones, 3-hydroxyhexane-2,5-dione (3-HHD), 1-hydroxyhexane-2,5-dione (1-HHD), and hexane-2,5-dione (HD) in water. Efficient transformation of furfural to LA over a range of η5-Cp-Ru-pyridylamine complexes is substantially affected by the Namine-substituents, where a η5-Cp-Ru-N-propylpyridylamine complex ([Ru]-2) exhibited higher catalytic activity in comparison to other η5-Cp-Ru-pyridylamine and η5-Cp-Ru-pyridylimine complexes. The relative catalytic activity of the studied complexes demonstrated a substantial structure-activity relationship which is governed by the basicity of Namine, steric hindrance at Namine, and the hemilabile nature of the coordinated pyridylamine ligands.
- Dwivedi, Ambikesh D.,Sahu, Vinod K.,Mobin, Shaikh M.,Singh, Sanjay K.
-
supporting information
p. 4777 - 4787
(2018/04/25)
-
- Molecular probes for ascorbate detection and methods of use
-
Described are metal complexes for the selective detection of ascorbic acid or ascorbate. The metal complexes act as molecular sensors, and are useful in detecting ascorbate in live biological samples, commercial samples, or both. The selective ascorbate sensing involves an ascorbate-selective bond cleavage reaction. The bond cleavage is not limited to the construction of molecular sensors, but also includes other stimuli-responsive materials, i.e., materials that adopt a physical state, such as gel formation, upon ascorbate-selective bond cleavage of the metal complexes.
- -
-
Page/Page column 46; 47; 48
(2018/07/30)
-
- Preparation of the Ru3(CO)8-pyridine-alcohol cluster and its use for the selective catalytic transformation of primary to secondary amines
-
The synthesis of pyridine alcohol based ruthenium carbonyl clusters Ru3(hep)2(CO)8 (1), Ru3(hpp)2(CO)8 (2), and Ru3(bhmp-H)2(CO)8 (3) {hep-H = 2-(2-hydroxyethyl)pyridine, hpp-H = 2-(3-hydroxypropyl)pyridine and bhmp-H2 = 2,6-bis(hydroxymethyl)pyridine} has been carried out by the reaction of the corresponding pyridine-alcohol ligands with Ru3(CO)12. Clusters 1-3 have been characterized using elemental analysis, NMR, FT-IR, mass spectrometry and single-crystal X-ray structures. The clusters were explored for the selective catalytic transformation of primary amines into secondary amines using alcohols as the mono-alkylating agents via hydrogen transfer reactions. All three display efficient catalytic activity with 1 being the most effective.
- Singh, Ajeet,Mobin, Shaikh M.,Mathur, Pradeep
-
p. 14033 - 14040
(2018/11/23)
-
- COMPOUNDS
-
The invention provides compounds for use in a method of treating and/or preventing a bacterial infection in a human or non-human mammal, said method comprising administration of said compound in combination with (either simultaneously, separately, or sequentially) a β-lactam antibiotic, wherein said compound has the general formula I: (I) (wherein: Q is a lipophilic, zinc chelating moiety which is selective for Zn2+ ions and which comprises at least one, preferably two or more (e.g 2, 3 or 4), optionally substituted, unsaturated heterocyclic rings, e.g. 5 or 6-membered heterocyclic rings (such rings preferably include at least one heteroatom selected from N, S and O, preferably N); wherein any optional substituents may be selected from C1-6 alkyl, C1-6 alkoxy, halogen, nitro, cyano, amine, and substituted amine; each L, which may be the same or different, is a covalent bond or a linker; each W, which may be the same or different, is a non-peptidic hydrophilic group which comprises one or more hydroxy groups; and x is an integer from 1 to 3) or a stereoisomer, pharmaceutically acceptable salt or prodrug thereof.
- -
-
Page/Page column 166-167
(2018/03/09)
-
- Stereospecific control of the metal-centred chirality of rhodium(III) and iridium(III) complexes bearing tetradentate CNN′P ligands
-
Ligands LH1-LH3 have been prepared by two successive condensation/reduction steps. These ligands react with MCl3 (M = Rh, Ir) rendering the trichlorido complexes [MCl3(κ3N,N′,P-LH)] (M = Rh, LH = LH1 (1), LH2 (2), LH3 (3); M = Ir, LH = LH1, (4)) as racemic mixtures of fac and mer isomers. Only one of the two possible fac isomers was detected. The mer isomer of the rhodium compounds 1-3 quantitatively isomerizes to the more stable fac isomer, whereas the mer isomer of the iridium complex 4 does not. DFT calculations indicate a dissociative pathway for this isomerization. In the presence of acetate or trifluoroacetate, complexes 1-3 or 4, respectively, undergo cyclometallation of their free benzylic arm affording the corresponding dichlorido compounds [MCl2(κ4C,N,N′,P-L)] (M = Rh, L = L1 (5), L2 (6), L3 (7); M = Ir, L = L1 (8)). Only one of the three possible enantiomeric pairs of coordination isomers was detected. The configuration at the stereogenic centres, namely the metal and the iminic nitrogen atom is stereospecifically predetermined. DFT calculations reveal that the cyclometallation follows an acetate-assisted mechanism and indicate that the isolated isomers are the most stable. Complexes 1-8 have been characterized by analytical and spectroscopic means and by the determination of the crystal structures of the complexes 1, 3 and 5-8 by X-ray diffractometry.
- Carmona, María,Rodríguez, Ricardo,Méndez, Isabel,Passarelli, Vincenzo,Lahoz, Fernando J.,García-Ordu?a, Pilar,Carmona, Daniel
-
supporting information
p. 7332 - 7350
(2017/07/10)
-
- Expanding the Boundaries of Water-Tolerant Frustrated Lewis Pair Hydrogenation: Enhanced Back Strain in the Lewis Acid Enables the Reductive Amination of Carbonyls
-
The development of a boron/nitrogen-centered frustrated Lewis pair (FLP) with remarkably high water tolerance is presented. As systematic steric tuning of the boron-based Lewis acid (LA) component revealed, the enhanced back-strain makes water binding increasingly reversible in the presence of relatively strong base. This advance allows the limits of FLP's hydrogenation to be expanded, as demonstrated by the FLP reductive amination of carbonyls. This metal-free catalytic variant displays a notably broad chemoselectivity and generality.
- Dorkó, éva,Szabó, Márk,Kótai, Bianka,Pápai, Imre,Domján, Attila,Soós, Tibor
-
supporting information
p. 9512 - 9516
(2017/08/01)
-
- Experimental and mechanistic insights into copper(ii)-dioxygen catalyzed oxidative: N -dealkylation of N -(2-pyridylmethyl)phenylamine and its derivatives
-
A di-(2-pyridylmethyl)phenylamine ((PyCH2)2NPh) supported Cu(ii)/O2 catalytic system was explored with the synthesis of pyridylmethyl-based compounds of carboxylate (PyCOOH), amide (PyC(O)NHPh), and imine (PyCHNPh) from the oxidative N-dealkylation of N-(2-pyridylmethyl)phenylamine (PyCH2NHPh) and its derivatives, by means of controlling the addition of a base and/or water to the reaction system under a dioxygen atmosphere at room temperature. Experimental studies showed that the imine and amide species could be precursors in succession in the way to the final oxidation state of carboxylates. A cyclic catalytic mechanism was proposed including the base triggered C-H bond activation of the 2-pyridylmethyl group (PyCH2-) and the intermolecular Cu-OOH α-hydrogen atom abstraction from the coordinated imine substrate (PyCHNPh).
- Wang, Yang,Liu, Haixiong,Zhang, Xiaofeng,Zhang, Zilong,Huang, Deguang
-
supporting information
p. 9164 - 9168
(2017/11/15)
-
- Scalable synthesis of secondary and tertiary amines by heterogeneous Pt-Sn/γ-Al2O3catalyzed N-alkylation of amines with alcohols
-
Synthesis of secondary and tertiary amines has been efficiently realized from the N-alkylation of amines with alcohols by means of heterogeneous bimetallic Pt-Sn/γ-Al2O3catalyst (0.5?wt % Pt, molar ratio Pt:Sn?=?1:3) through a borrowing hydrogen strategy. The Pt-Sn/γ-Al2O3catalyst has exhibited very high catalytic activity towards a wide range of amines and alcohols, and can be conveniently recycled without Pt metal leaching. The present protocol was applied for the synthesis of N-phenylbenzylamine in 96% isolated yield from aniline and benzyl alcohol on a 2.1?kg scale of the substrates, demonstrating its potential applicability for higher-order amine synthesis.
- Wu, Kaikai,He, Wei,Sun, Chenglin,Yu, Zhengkun
-
supporting information
p. 8516 - 8521
(2016/11/28)
-
- Cu(I)-catalyzed transannulation of N -heteroaryl aldehydes or ketones with alkylamines via C(sp3)-H amination
-
A copper(I)-catalyzed direct transannulation of N-heteroaryl aldehydes or ketones with alkylamines via Csp3-H amination has been achieved using molecular oxygen as a sole oxidant. N-Heteroarenes are employed as the amine source. This transformation provides a rapid and concise access to multifunctional imidazo[1,5-a]pyridines.
- Li, Mingyang,Xie, Ying,Ye, Yong,Zou, Yong,Jiang, Huanfeng,Zeng, Wei
-
supporting information
p. 6232 - 6235
(2015/02/19)
-
- Efficient cobalt-catalyzed oxidative conversion of lignin models to benzoquinones
-
Phenolic lignin model monomers and dimers representing the primary substructural units of lignin were successfully oxidized to benzoquinones in high yield with molecular oxygen using new Co-Schiff base catalysts bearing a bulky heterocyclic nitrogen base as a substituent. This is the first example of a catalytic system able to convert both S and G lignin model phenols in high yield, a process necessary for effective use of lignin as a chemical feedstock.
- Biannic, Berenger,Bozell, Joseph J.
-
supporting information
p. 2730 - 2733
(2013/07/26)
-
- Design of a dinuclear nickel(II) bioinspired hydrolase to bind covalently to silica surfaces: Synthesis, magnetism, and reactivity studies
-
Presented herein is the design of a dinuclear NiII synthetic hydrolase [Ni2(HBPPAMFF)(μ-OAc)2(H2O)] BPh4 (1) (H2BPPAMFF = 2-[(N-benzyl-N-2-pyridylmethylamine) ]-4-methyl-6-[N-(2-pyridylmethyl)aminomethyl)])-4-methyl-6-formylphenol) to be covalently attached to silica surfaces, while maintaining its catalytic activity. An aldehyde-containing ligand (H2BPPAMFF) provides a reactive functional group that can serve as a cross-linking group to bind the complex to an organoalkoxysilane and later to the silica surfaces or directly to amino-modified surfaces. The dinuclear NiII complex covalently attached to the silica surfaces was fully characterized by different techniques. The catalytic turnover number (kcat) of the immobilized Ni IINiII catalyst in the hydrolysis of 2,4- bis(dinitrophenyl)phosphate is comparable to the homogeneous reaction; however, the catalyst interaction with the support enhanced the substrate to complex association constant, and consequently, the catalytic efficiency (E = k cat/KM) and the supported catalyst can be reused for subsequent diester hydrolysis reactions.
- Piovezan, Clovis,Silva, Jaqueline M. R.,Neves, Ademir,Bortoluzzi, Adailton J.,Haase, Wolfgang,Tomkowicz, Zbigniew,Castellano, Eduardo E.,Hough, Tessa C. S.,Rossi, Liane M.
-
experimental part
p. 6104 - 6115
(2012/07/14)
-
- Synthesis of α-amino acids through samarium(II) iodide promoted reductive coupling of nitrones with CO2
-
Several N-benzylnitrones reacted with carbon dioxide in the presence of samarium(II) iodide leading to α-amino acids as the products of reductive C-C coupling. The best selectivities were observed at a carbon dioxide pressure of 50 bar at ambient temperature. The influences of different functional groups in the nitrone backbone and of the coordinating additives to samarium(II) iodide on the product distribution were investigated. The racemic α-amino acids were obtained in up to 70% yield based on HPLC data. A novel approach to the synthesis ofα-amino acids is disclosed, involvingC-carboxylation of nitrones by gaseous CO2 under reductive coupling reaction conditions (SmI2, 0.1 M in THF) at ambient temperature and 50 bar of CO 2 pressure. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
- Prikhod'Ko, Alexander,Walter, Olaf,Zevaco, Thomas A.,Garcia-Rodriguez, Jaime,Mouhtady, Omar,Py, Sandrine
-
supporting information; experimental part
p. 3742 - 3746
(2012/09/25)
-
- Functional models for enzyme-substrate adducts of catechol dioxygenase enzymes: The Lewis basicity of facially coordinating tridentate phenolate ligands tunes the rate of dioxygenation and product selectivity
-
A few iron(III) 3,5-di-tert-butylcatecholate (DBC2-) adducts of the type [Fe(L)(DBC)(CH3OH)], where L is a tridentate substituted monophenolate ligand such as 2-((N-benzylpyrid-2-ylmethylamino)methyl)phenol (H(L1)), 2-((N-benzylpyrid-2-ylmethylamino)-methyl)-4,6-dimethylphenol (H(L2)), 2-((N-benzylpyrid-2-ylmethylamino)methyl)-4,6-di-tert-butylphenol (H(L3)) and 2-((N-benzylpyrid-2-ylmethylamino)methyl)-4-nitrophenol (H(L4)), have been isolated and characterized by elemental and ESI-MS analysis. The spectral and electrochemical properties and dioxygenase activities of the adducts have been studied in methanol solution. Upon varying the substituents on the phenolate ring from electron-releasing to electron-withdrawing, the redox potential of DBSQ/DBC2- couple is shifted to a more positive value indicating an increase in covalency of iron(III)-catecholate bonds. All the complexes elicit cleavage of DBC2- using molecular oxygen to afford both intra- (I) and extradiol (E) cleavage products with the product selectivity (E/I) varying in the range 0.3-1.9. Interestingly, the incorporation of electron-withdrawing substituents facilitates the regioselective extradiol cleavage of catechol while that of electron-releasing substituents facilitate the regioselective intradiol cleavage.
- Visvaganesan, Kusalendiran,Ramachitra, Somasundaram,Palaniandavar, Mallayan
-
experimental part
p. 87 - 94
(2012/02/03)
-
- Pt-Sn/γ-Al2O3-catalyzed highly efficient direct synthesis of secondary and tertiary amines and imines
-
Versatile syntheses of secondary and tertiary amines by highly efficient direct N-alkylation of primary and secondary amines with alcohols or by deaminative self-coupling of primary amines have been successfully realized by means of a heterogeneous bimetallic Pt-Sn/γ-Al2O3 catalyst (0.5 wt % Pt, Pt/Sn molar ratio=1:3) through a borrowing-hydrogen strategy. In the presence of oxygen, imines were also efficiently prepared from the tandem reactions of amines with alcohols or between two primary amines. The proposed mechanism reveals that an alcohol or amine substrate is initially dehydrogenated to an aldehyde/ketone or NH-imine with concomitant formation of a [PtSn] hydride. Condensation of the aldehyde/ketone species or deamination of the NH-imine intermediate with another molecule of amine forms an N-substituted imine which is then reduced to a new amine product by the in-situ generated [PtSn] hydride under a nitrogen atmosphere or remains unchanged as the final product under an oxygen atmosphere. The Pt-Sn/γ-Al2O 3 catalyst can be easily recycled without Pt metal leaching and has exhibited very high catalytic activity toward a wide range of amine and alcohol substrates, which suggests potential for application in the direct production of secondary and tertiary amines and N-substituted imines.
- He, Wei,Wang, Liandi,Sun, Chenglin,Wu, Kaikai,He, Songbo,Chen, Jiping,Wu, Ping,Yu, Zhengkun
-
experimental part
p. 13308 - 13317
(2012/02/02)
-
- Multicomponent reaction of imidazo[1,5- a ]pyridine carbenes with aldehydes and dimethyl acetylenedicarboxylate or allenoates: A straightforward approach to fully substituted furans
-
The facile three-component reactions of N,N-substituted imidazo[1,5-a]pyridine carbenes, namely imidazo[1,5-a]pyridin-3-ylidenes, with aldehydes and DMAD or allenoates were disclosed. Both reactions proceeded via tandem nucleophilic addition, [3 + 2]-cycloaddition, and ring transformation to produce different 4-[(2-pyridyl)methyl]aminofuran derivatives generally in moderate yields. This work not only 'rovided the first example of the application of imidazo[1,5-a]pyridin-3-ylidenes in organic synthesis but also developed a straightforward approach to fully substituted furans that are not easily accessible by other methods.
- Pan, Huan-Rui,Li, Yong-Jia,Yan, Cai-Xia,Xing, Juan,Cheng, Ying
-
supporting information; experimental part
p. 6644 - 6652
(2010/11/17)
-
- Reductive amination using ammonia borane
-
A variety of primary, secondary, and tertiary amines were prepared in 84-95% yields using ammonia borane for the reductive amination of aldehydes and ketones in the presence of titanium isopropoxide.
- Veeraraghavan Ramachandran,Gagare, Pravin D.,Sakavuyi, Kaumba,Clark, Paul
-
experimental part
p. 3167 - 3169
(2010/08/05)
-
- Aminophosphinic acids in a pyridine series, Part 2: Synthesis of 2-, 3-, and 4-pyridyl derivatives of 1-(Benzylamino)-methyl-H-phosphinic Acids
-
New 2-pyridyl, 3-pyridyl, and 4-pyridyl derivatives of 1-[N-(benzyl)amino]- methyl-H-phosphinic acid were prepared by the addition of bis(trimethylsilyl) phosphonite to the corresponding imines and subsequent methanolysis of the addition products. Treatment of the 2-pyridyl- and 1-(4-pyridyl)-1-(benzylamino) -methyl-H-phosphinic acids with aqueous mineral acids leads to cleavage and formation of the corresponding secondary amines and phosphorous acid (H3PO3).
- Goldeman, Waldemar,Boduszek, Bogdan
-
scheme or table
p. 1413 - 1425
(2010/03/24)
-
- Pentacyclo-undecane derived cyclic tetra-amines: Synthesis and evaluation as potent anti-tuberculosis agents
-
As part of an ongoing effort to develop highly potent anti-tuberculosis agents, fourteen pentacyclo-undecane (PCU) tetra-amine compounds were synthesized and screened for their in vitro anti-mycobacterial activity against two TB strains, H37Rv and XDR 194 [an extensively drug-resistant strain of tuberculosis]. Using the broth macrodilution method, nitrofuranylamide based compounds (6a and 6b) showed almost similar activities against the H37Rv strain of Mycobacterium tuberculosis when compared with the control drug, ethambutol. N-Geranyl piperazine PCU (8a) and trans-trans farnesyl piperazine PCU (8b) were 3.2 and 3.7 times more potent than commercially available ethambutol. Both isoprenyl PCU tetra-amine derivatives and N-decyl piperazine PCU (9a) were highly active against the XDR 194 strain of tuberculosis with MICs in the range of 0.63-3.02 μM. Cytotoxicities (IC50) of isoprenyl based compounds (8a, 8b) and compound 9a were tested on a mammalian cell line [MDBK (Madin Darby bovine kidney epithelium)] with values of 30, 24 and 25 μM respectively.
- Onajole, Oluseye K.,Govender, Karnishree,Govender, Patrick,van Helden, Paul D.,Kruger, Hendrik G.,Maguire, Glenn E.M.,Muthusamy, Karen,Pillay, Manormoney,Wiid, Ian,Govender, Thavendran
-
experimental part
p. 4297 - 4305
(2010/02/27)
-
- A general one-step synthesis of multidentate (pyridylalkyl)amines from mono-, bis-, tris- and tetrakis(bromomethyl)benzenes: Potential ligands for supramolecular assembly
-
The synthesis of new multidentate nitrogen-containing ligands is of ongoing interest. In this report, the one-step syntheses of a series of (pyridylalkyl)amine derivatives is described. The reported compounds contain both pyridine rings and sp3-hybridized nitrogen as potential donor sites. The general synthetic method involves a room temperature reaction of mono-, bis-, tris-, or tetrakis(bromomethyl)benzenes with an excess of (pyridylmethyl)amine in tetrahydrofuran. The products can be purified by distillation, chromatography or recrystallization and are obtained in fair to good yields. The advantages of this synthetic method are the procedural simplicity and the ready availability of the starting materials. The applicability of these compounds in supramolecular chemistry is demonstrated by the reaction of two of the described ligands with silver(I) salts. Georg Thieme Verlag Stuttgart.
- Sengupta, Parbati,Henkes, Amanda E.,Kumar, Mananjali K.,Zhang, Hongming,Son, David Y.
-
-
- Zinc and enolato-magnesium complexes based on bi-, tri- and tetradentate aminophenolate ligands
-
The coordination chemistry of a series of potentially tetra-, tri- and bi-dentate aminophenol pro-ligands ([L1]H-[L5]H) with magnesium and zinc derivatives has been studied. Reactions of the pro-ligands [L1]H, [L2]H and [L3]H with one equiv. of ZnEt2 or Zn(N(SiMe3)2)2 in toluene at room temperature afford cleanly, via ethane or amine elimination, the ethyl- and amido-zinc complexes 1-4. Complexes [L4]ZnEt (5) and [L 4]Zn(N(SiMe3)2)2 (6) derived from the tridentate pro-ligand [L4]H were prepared in 84% and 76% yields, following similar alkane and amine elimination protocols, respectively. The 1:1 reactions of bidentate pro-ligand [L5]H with ZnEt2 or Zn(N(SiMe3)2)2 in toluene using different reaction protocols systematically yielded mixtures of the bis(ligand) complex [L5]2Zn (7) and the corresponding ethyl-{[L 5]ZnEt}n (8; n = 1 or 2) or amido- {[L5] Zn(N(SiMe3)2)}n complexes (9; n = 1 or 2). The synthesis of magnesium-enolate complexes 10 and 11 was carried out in a one-pot, two-step procedure by first reacting pro-ligands [L1]H and [L 4]H with one equiv. of Mg(n,sBu)2 to generate the corresponding {[Ln]Mg(n,sBu)}n species, which were further reacted with one equiv. of 2,4,6-Me3C6H2COMe. All complexes have been characterized by multinuclear NMR, elemental analysis, and by single-crystal X-ray diffraction studies for five-coordinate magnesium complex 10, and four-coordinate Zn complexes 3-7. Preliminary studies indicate that magnesium species 10 and 11 as well as zinc complexes 1 and 5 are not active initiators for the polymerization of methyl methacrylate, even in combination with one equiv. of Li[OC(=CH2)(2,4,6-Me3C 6H2)], while zinc complexes 2, 4 and 6 are effective initiators for the ring-opening polymerization of ε-caprolactone and rac-lactide at 20°C. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2008.
- Zheng, Zhanjiang,Zhao, Gang,Fablet, Remy,Bouyahyi, Miloud,Thomas, Christophe M.,Roisnel, Thierry,Casagrande Jr., Osvaldo,Carpentier, Jean-Francois
-
experimental part
p. 2279 - 2291
(2009/03/11)
-
- Synthesis and NMR elucidation of novel penta-cycloundecane amine derivatives as potential antituberculosis agents
-
The synthesis and NMR elucidation of five novel penta-cycloundecane amine derivatives are reported. These compounds are potential antituberculosis agents. The 1H and 13C spectra showed major overlapping of methine signals of the cage skeleton making it extremely difficult to elucidate these compounds. The overlapping occurs as a result of the additions made to the carbonyl carbon (C-8/C-11) of the cage. The two-dimensional NMR technique proved to be a useful tool in overcoming this problem. All compounds reported are meso compounds thereby not only simplifying the NMR structure elucidation, but also making it indeed possible. Copyright
- Onajole, Oluseye K.,Govender, Thavendran,Makatini, Maya,Kruger, Hendrik G.
-
experimental part
p. 1007 - 1014
(2009/04/10)
-
- Half-sandwich η6-benzene Ru(II) complexes of phenolate-based pyridylalkylamine/alkylamine ligands: Synthesis, structure, and stabilization of one-electron oxidized species
-
Four half-sandwich ruthenium(II) complexes [(η6-C6H6)Ru(L1-O)][PF6] (1), [(η6-C6H6)Ru(L2-O)][PF6] (2), [(η6-C6H6)Ru(L3-O)][PF6] (3), [(η6-C6H6)Ru(L4-O)][PF6] (4a), and [(η6-C6H6)Ru(L4-O)][BPh4] (4b) [L1-OH, 4-nitro-6-{[(2′-(pyridin-2-yl)ethyl)methylamino]methyl}-phenol; L2-OH, 2,4-di-tert-butyl-6-{[(2′-(pyridin-2-yl)ethyl)methylamino]methyl}-phenol; L3-OH, 2,4-di-tert-butyl-6-{[2′-((pyridin-2-yl)benzylamino)methyl}-phenol; L4-OH, 2,4-di-tert-butyl-6-{[(2′-imethylaminoethyl)methylamino]methyl}-phenol (L4-OH)], supported by a systematically varied series of tridentate phenolate-based pyridylalkylamine and alkylamine ligands are reported. The molecular structures of 1-3, 4a, and 4b have been elucidated in solution using 1H NMR spectroscopy and of 1, 3, and 4b in the solid state by X-ray crystallography. Notably, due to coordination by the ligands the Ru center assumes a chiral center and in turn the central amine nitrogen also becomes chiral. The 1H NMR spectra exhibit only one set of signals, suggesting that the reaction is completely diastereoselective [1: SRu,SN/RRu,RN; 2: RRu,RN/SRu,SN; 3: SRu,RN/RRu,SN; 4b: SRu,RN/RRu,SN]. The crystal packing in 1 and 3 is stabilized by C-H...O interactions, in 4b no meaningful secondary interactions are observed. From the standpoint of generating phenoxyl radical, as investigated by cyclic voltammetry (CV), complex 1 is redox-inactive in MeCN solution. However, 2, 3, and 4a generate a one-electron oxidized phenoxyl radical coordinated species [2]2+{radical dot}, [3]2+{radical dot}, and [4a]2+{radical dot}, respectively. The radical species are characterized by CV, UV-Vis, and EPR spectroscopy. The stability of the radical species has been determined by measuring the decay constant (UV-Vis spectroscopy).
- Mishra, Haritosh,Mukherjee, Rabindranath
-
p. 3248 - 3260
(2008/02/08)
-
- Aminophosphine oxides in a pyridine series. Studies on the cleavage of pyridine-2- and pyridine-4-yl-(N-benzylamino)-methyldiphenylphosphine oxides in acidic solutions
-
The synthesis and reactions of 1-(N-benzylamino)-1-(2-pyridyl)- and 1-(N-benzylamino)-1-(4-pyridyl)-methyldiphenylphosphine oxides are described. It was found that these compounds were exceptionally easy to cleave in aqueous sulfuric acid solutions to form diphenylphosphinic acid and the corresponding N-(pyridylmethyl)-benzylamines. The structure of a single diastereoisomer, that is, the (R)-(+)-1-[N-(α-methylbenzylamino)]-1-(4-pyridyl)-(S)-methyldiphen ylphosphine oxide was determined by X-ray crystallography. The acidic alcoholysis of the selected model chiral pyridine aminophosphine oxides was investigated by means of 31P NMR spectroscopy. The cleavage kinetics were also studied. On the basis of the obtained results, a mechanism of the cleavage was formulated.
- Goldeman, Waldemar,Olszewski, Tomasz K.,Boduszek, Bogdan,Sawka-Dobrowolska, Wanda
-
p. 4506 - 4518
(2007/10/03)
-
- Aminophosphinic acids in a pyridine series: Cleavage of pyridine-2- and pyridine-4-methyl(amino)phosphinic acids in acidic solutions
-
The synthesis of a series of new pyridine aminomethylphosphinic acids is described. These compounds were obtained in the reaction of the corresponding pyridine aldehydes with primary amines and with ethyl phenylphosphinate, or methylphosphinate, in the presence of bromotrimethylsilane. In aqueous, strong acid solutions, pyridine aminophosphinic acids were split, forming the phenyl-, or methylphosphonic, acid and the corresponding secondary pyridyl-alkylamines. The kinetics of some observed cleavages were measured, and a mechanism of the cleavage has been proposed. Copyright Taylor & Francis Group, LLC.
- Boduszek, Bogdan,Olszewski, Tomasz,Goldeman, Waldemar,Konieczna, Magdalena
-
p. 787 - 795
(2007/10/03)
-
- General and environmentally friendly synthesis of heterocyclic multidentate molecules based on microwave-assisted heating protocol
-
An efficient microwave heating methodology for the synthesis of heterocyclic multidentate molecules is reported. Each compound was obtained with high yield and purity in a few minutes from easily available starting materials such as amines, heteroaldehydes and N-hydroxymethyl pyrazoles or triazoles. In addition, this approach allows synthesis without any solvent or organic and inorganic by-products.
- Regnier, Thomas,Lavastre, Olivier
-
p. 155 - 159
(2007/10/03)
-
- A Simple Synthesis of Pyridine Aminophosphinic Acids and Pyridine Aminophosphine Oxides. The Unusual Cleavage of Pyridylmethyl-(N-benzylamino)-phenylphosphinic Acids and Phosphine Oxides in Acidic Solutions
-
Pyridine aminophosphinic acids were synthesized in reaction, of N-(benzyl)-pyridylmethylimines with ethyl phenylphosphinate, in the presence of bromotrimethylsilane. Pyridine aminophosphine oxides were obtained in excellent yields by treatment of the corresponding imines with diphenylphosphine oxide. Among these compounds, the 2-pyridyl and 4-pyridyl derivatives were subject to a simple cleavage in aqueous mineral acid solutions. Products of the cleavages were N-(pyridylmethyl)benzylamines and phenylphosphonic (or diphenylphosphinic) acid, respectively.
- Boduszek, Bogdan
-
p. 4087 - 4094
(2007/10/03)
-
- Ketoester methacrylate resin, secondary amine clean-up in the presence of primary amines
-
A ketoester resin was developed as the basis for a selective scavenger for primary amines in the presence of secondary amines. The utility of the scavenger was demonstrated with a range of reductive amination chemistries with both mono- and diamines. The resin's specificity is based on the removal of the primary amines via their enamines.
- Yu,Alesso,Pears,Worthington,Luke,Bradley
-
p. 1947 - 1952
(2007/10/03)
-
- 1-aminophosphonic acids and esters bearing heterocyclic moiety. Part 2. 1 pyridine, pyrrole and emidazole derivatives
-
The benzylic amines (benzylamine, benzhydrylamine and benzyl carbamate) were applied in the synthesis of aminophosphonates derived from pyridine, pyrrole and imidazole. The Schiff bases obtained from corresponding heterocyclic aldehydes and benzylic amines were caused to react with diphenyl phosphorate or dibenzyl phosphonate to form corresponding heterocyclic aminophosphonates in good yields. The N-(benzylamino)-phosphonates were deblocked by catalytic hydrogenolysis. The benzhydryl group from the phosphonates was removed by acidic hydrolysis, and the carbobenzyloxy group from the phosphonates can be easy removed by treatment with a solution of 30% HBr in acetic acid, as well. It was found that during acidic hydrolysis of 2-and 4-pyridylmethylaminophosphonates a rearrangement occurred, combined with a cleavage of C-P bond in the phosphonate molecules and subsequent formation of the corresponding amines.
- Boduszek, Bogdan
-
p. 209 - 218
(2007/10/03)
-
- The acidic cleavage of pyridylmethyl(amino)phosphonates. Formation of the corresponding amines
-
Hydrolysis of 3-pyridylmethyl(amino)phosphonates by means of 20% aq. hydrochloric acid gave corresponding 3-pyridimethyl(amino)phosphonic acids, as expected. However, hydrolysis of 2- and 4-pyridylmethyl(amino)phosphonates led to decomposition of the phosphonates with a cleavage of C-P bond and formation of the corresponding amines. The leaving phosphorus moiety was identified as phosphoric acid. The scope of the reaction is limited to 2- and 4-pyridylmethyl derivatives of aminophosphonic acids and their esters, as well as to the derivatives possessing similar structure. On the contrary, the basic hydrolysis of 2- and 4-pyridylmethyl(amino)phosphonates led to the corresponding monoalkyl esters of the aminophosphonates, and no cleavage of C-P bond was observed in those cases.
- Boduszek, Bogdan
-
p. 12483 - 12494
(2007/10/03)
-