Showing papers on "Morpholine published in 2013"
TL;DR: A straightforward, isocyanate-free method for the synthesis of functionalized polyurethanes, based on amine–thiol–ene conjugation, was elaborated and the kinetic profile of this reaction sequence was revealed, excluding the occurrence of competing reactions, such as aza-Michael addition and disulfide formation.
85 citations
TL;DR: In this article, a proof of concept of laser-assisted heterogeneously catalysed processes at room temperature using silica supported gold nanoparticles is reported, where Au/SiO2 nanoparticles were laser-irradiated at 532 nm (SPR maximum absorbance) to catalyse the selected reaction, namely the production of 4-benzoylmorpholine from benzaldehyde and morpholine via amide formation, for which quantitative yields to the target amide were obtained after 3-5 h of reaction.
53 citations
TL;DR: Antimicrobial and antiurease activities of newly synthesized compounds were investigated and Compound 10 proved to be the most potent showing an enzyme inhibition activity with an IC50 = 2.37 ± 0.19 μM.
Abstract: 2-[6-(Morpholin-4-yl)pyridin-3-ylamino]acetohydrazide (4) was obtained starting from 6-morpholin-4-ylpyridin-3-amine (2) via the formation of ester (3) and then converted to the corresponding Schiff bases (5, 6) with the reaction with aromatic aldehydes. The carbothioamide (9), obtained from the reaction of hydrazide with phenylisothiocyanate, was converted to the corresponding 1,2,4-triazole (11) and 1,3,4-thiadiazole (12) derivatives by the treatment with NaOH or H2SO4, respectively. The cyclocondenzation of 9 with 4-chlorophenacyl bromide or ethyl bromoacetate produced the corresponding 1,3-thiazole (10) or 1,3-thiazolidine derivatives (13), respectively. Antimicrobial and antiurease activities of newly synthesized compounds were investigated. Some of them were found to be active on M. smegmatis, and they displayed activity toward C. albicans and S. cerevisiae in high concentration. Compound 10 proved to be the most potent showing an enzyme inhibition activity with an IC50 = 2.37 ± 0.19 μM.
46 citations
TL;DR: None of the compounds showed a significant antitumor activity on 60 human tumor cell lines, however, compounds 6g and 6f with benzothiazole moiety showed promising activity against Escherichia coli compared to ampicillin; compounds 6d, 6j bearing triazole and morpholine showed promising antitubercular activity compared to rifampicin.
45 citations
TL;DR: In this paper, the structural motifs and trends of naphthalene-1,5-diphosphonic acid with morpholine were analyzed. But the authors focused on the role of conformational flexibility of the acids on the dimensionality of the final hydrogen bond network, which is higher for H4NDP(1C,5C).
Abstract: Naphthalene-1,5-diphosphonic acid [C10H6(PO3H2)2, H4NDP(1,5), 1] and its more flexible counterpart, naphthalene-1,5-bis(methylphosphonic) acid [C10H6(CH2PO3H2)2, H4NDP(1C,5C), 2], have been synthesized, characterized, and used as building blocks in supramolecular assemblies with 4-(N,N-dimethylamino)pyridine (DMAP) and morpholine. The two acids generate two distinct solvatomorphs each, with and without dimethyl sulfoxide (DMSO) molecules. The two adducts of H4NDP(1,5) with DMAP (3A and 3B) reveal conformational polymorphism caused by the rotation of phosphonic groups. The two adducts of H4NDP(1C,5C) show unexpected structural diversity, generating a symmetric hydrogen bond and creating a layered structure, 4A, or a channel structure, 4B. The adducts of both acids with morpholine (5A and 5B) allow for observing the influence of the conformational flexibility of the acids on the dimensionality of a final hydrogen bond network, which is in general higher for H4NDP(1C,5C). The structural motifs and trends are...
45 citations
TL;DR: The transition structures for the 1,3-dipolar cycloadditions of phenyl azide to enamines derived from acetophenone or phenylacetaldehyde and piperidine, morpholine, or pyrrolidine were located using quantum mechanical methods.
Abstract: The transition structures for the 1,3-dipolar cycloadditions of phenyl azide to enamines derived from acetophenone or phenylacetaldehyde and piperidine, morpholine, or pyrrolidine were located using quantum mechanical methods. These cycloadditions were studied experimentally in 1975 by Meilahn, Cox, and Munk (J. Org. Chem.1975, 40, 819–823). Calculations were carried out with M06-2X/6-311+G(d,p), SCS-MP2/6-311+G(d,p)//M06-2X/6-311+G(d,p), and B97D/6-311+G(d,p) methods with the IEF-PCM solvation model for chloroform and ethanol. The distortion/interaction model was utilized to understand mechanisms, reactivities, and selectivities.
42 citations
TL;DR: On all fours: The title reaction with (Ipc)2 BH provides tetrasubstituted enolborinates which undergo aldol reactions with aldehydes to form products with all-carbon quaternary centers with exceptional diastereo- and enantioselectivity.
Abstract: On all fours: The title reaction with (Ipc)2 BH provides tetrasubstituted enolborinates which undergo aldol reactions with aldehydes to form products with all-carbon quaternary centers with exceptional diastereo- and enantioselectivity. A change to the substitution pattern of the starting amide leads to either diastereomer of the α-methyl-α-ethyl-β-hydroxy carboxamide (1 or 2).
41 citations
TL;DR: The experiments were conducted using morpholine as a representative secondary amine as a potential CO₂ capture solvent with 100 ppm standard NO₁ gas to better understand the nitrosamine reaction pathways under scrubber and stripper conditions and the roles of nitrite and nitrite were probed.
Abstract: The amine assisted CO2 capture process from coal fired power plants strives for the determination of degradation components and its consequences. Among them, nitrosamine formation and their emissions are of particular concern due to their environmental and health effects. The experiments were conducted using morpholine as a representative secondary amine as a potential CO2 capture solvent with 100 ppm standard NO2 gas to better understand the nitrosamine reaction pathways under scrubber and stripper conditions. The role of nitrite in the nitrosation reaction was probed at elevated temperatures. The effects of different concentrations of nitrite on morpholine were evaluated. Formation rate, decomposition rates, activation energy, and the possible reaction pathways are elaborated. Thermal stability tests at 135 °C indicated the decomposition of nitrosamines at the rate of 1 μg/(g h) with activation energy of 131 kJ/mol. The activation energy for the reaction of morpholine with sodium nitrite was found as 10...
34 citations
TL;DR: In this paper, a series of crosslinked and quaternized polyvinyl alcohol (QPVA) anion exchange membranes were prepared for application in alkaline anions exchange membrane fuel cells.
33 citations
TL;DR: In this article, four new mononuclear nickel(II) complexes were synthesized via Schiff-base formation by condensation between 2-benzoylpyridine and N-(2-aminoethyl)pyrrolidine.
32 citations
TL;DR: An efficient procedure has been developed for the preparation of tetrasubstituted unsymmetrical 1,4-enediones via copper-promoted autotandem catalysis and air as the oxidant.
Abstract: An efficient procedure has been developed for the preparation of tetrasubstituted unsymmetrical 1,4-enediones via copper-promoted autotandem catalysis and air as the oxidant. Various N-nucleophiles are compatible with this reaction, such as morpholine, piperidine, pyrrolidine, arylamines, pyrazole, imidazole, benzimidazole, and benzotriazole. This reaction also has significant advantages in easily available substrates, atom economy, bond-forming efficiency, and environmental benignity.
TL;DR: The structures of all the phosphazenes were determined using FTIR, MS, 1H, 13C, and 31P NMR and 2-dimensional NMR techniques as discussed by the authors.
Abstract: The condensation reactions of hexachlorocyclotriphosphazene (N3P3Cl6) with mono (1 and 2) and bisferrocenyldiamines (3–5 and 7) resulted in the formation of tetrachloro mono- (8 and 9) and bisferrocenylspirocyclotriphosphazenes (10–13) In addition the tetramorpholino mono- (8a and 9a) and bisferrocenylphosphazenes (10a–12a) were obtained from the reactions of the corresponding tetrachlorophosphazenes (8–12) with excess morpholine The structures of all the phosphazenes were determined using FTIR, MS, 1H, 13C, and 31P NMR and 2-dimensional NMR techniques The structures of 9a and 13 were determined by single crystal X-ray diffraction techniques Cyclic voltammetric investigations of compounds 8a, 9a, and 11a revealed that ferrocene redox centers undergo reversible oxidation These ferrocenylphosphazenes appear to be quite robust electrochemically Interactions between the compounds 8a, 9a, 11a, and 12a and pBR322 plasmid DNA were investigated by agarose gel electrophoresis [Supplementary materia
TL;DR: An efficient synthesis of thiazolo[5,4-d]pyrimidines using recyclable KF/alumina catalyst is reported, which shows induction of apoptosis in A549 cells at 10 μM and cleavage of PARP-1 and procaspase-3 inhibition which confirms their apoptosis-inducing activity.
TL;DR: In this article, density functional theory calculations have been performed to investigate the mechanisms of the Pd-catalyzed dearomatization reaction between chloromethylnaphthalene and the cyclic amine morpholine.
TL;DR: Gel electrophoresis experiments demonstrated that all the compounds were comparably efficient in DNA degradation process; however, luminescence quenching showed surprising dependence on the interactions strength of the used compounds with the albumins.
Abstract: Herein, a series of CuI or CuNCS complexes with neocuproine (2,9-dimethyl-1,10-phenanthroline: dmp) and two tris(aminomethyl)phosphines derived from morpholine (P(CH2 N(CH2 CH2 )2 O)3 ) or thiomorpholine (P(CH2 N(CH2 CH2 )2 S)3 ) were tested as cytotoxic agents in vitro towards mouse colon carcinoma (CT26) and human lung adenocarcinoma (A549). The studies showed that the complexes exhibit potential antitumor properties, displayed by IC50 values below 10 μm towards the tested cell lines, in the case of 4-h incubation time with the examined compounds. Moreover, a high antimicrobial activity of all the complexes was observed against Staphylococcus aureus and Candida albicans with minimal inhibitory concentrations equal to 1-2 μg/mL. To gain insight into the molecular mechanism of biological activity of the complexes, we investigated also their interactions with plasmid DNA (pUC18) and the human and bovine serum albumins. Gel electrophoresis experiments demonstrated that all the compounds were comparably efficient in DNA degradation process; however, luminescence quenching showed surprising dependence on the interactions strength of the used compounds with the albumins. Apart from exceptionally effective [CuI(dmp)P(CH2 N(CH2 CH2 )2 O)3 ], the complexes with P(CH2 N(CH2 CH2 )2 O)3 quenched more strongly luminescence of bovine serum albumin, while the complexes with P(CH2 N(CH2 CH2 )2 S)3 were more active in the quenching of human serum albumin luminescence.
TL;DR: In this paper, the properties of fully morpholine substituted sas 5c and sbs 6c phosphazenes were verified by X-ray diffraction analysis and the relationships between exocyclic OPN bond angles (alpha') and delta P-OPN shifts, and the correlation of Delta(P-N) values and Delta(delta P) or delta P -OPN shift were presented.
TL;DR: In this paper, a non-ionic liquid compound, morpholine, was suggested as a dual-function inhibitor by measuring hydrate-phase equilibria and a series of microscopic analyses [powder X-ray diffraction, solid-state 13C nuclear magnetic resonance (NMR), and Raman spectroscopy].
Abstract: The unexpected formation of gas hydrates during production and transportation processes in petroleum industries is known as a serious problem. To deal with this problem, the oil and gas industry has been searching for hydrate inhibitors that have great performance and cost effectiveness. Recently, ionic liquids (ILs) have been suggested as novel hydrate inhibitors that are able to act in both thermodynamic and kinetic ways (so-called dual-function inhibitors). In this paper, we suggest a non-ionic liquid compound, morpholine, as a dual-function inhibitor by measuring hydrate-phase equilibria and a series of microscopic analyses [powder X-ray diffraction, solid-state 13C nuclear magnetic resonance (NMR), and Raman spectroscopy]. Moreover, the formation kinetics of gas hydrates in the presence of morpholine was found to be better than two comparators, 1-ethyl-3-methylimidazolium tetrafluoroborate and polyvinylpyrrolidone. Such inhibition effects of morpholine are thought to be mainly attributed to the nucle...
TL;DR: Most of the synthesized compounds exhibited considerable selectivity against the MCF‐7 and C6 cell lines and anticancer activities were investigated.
Abstract: The synthesis of some new 1-(2-aryl-2-oxoethyl)-2-[(morpholine-4-yl)thioxomethyl]benzimidazole derivatives and investigation of their anticancer activities were the aims of this work. 2-(Chloromethyl)benzimidazole compound was reacted with sulfur and morpholine via Willgerodt–Kindler reaction to give 2-[(morpholine-4-yl)thioxomethyl]benzimidazole. Then, the obtained compound was reacted with appropriate a-bromoacetophenone derivatives in the presence of potassium carbonate to give the final products. Structure elucidation of the final compounds was achieved by FT-IR, 1 H NMR spectroscopy and MS spectrometry. The anticancer activities of the final compounds were evaluated by MTT assay, BrdU method, and flow cytometric analysis on C6, MCF-7, and A549 tumor cells. Most of the synthesized compounds exhibited considerable selectivity against the MCF-7 and C6 cell lines.
TL;DR: In this article, the Pd-S and Pd−Se bond lengths are in the ranges 2.2795(14) and 2.3541(6)−2.3632(15) A, respectively.
TL;DR: In this paper, the stability of Fe(III with two buffer families, tris(hydroxymethyl)aminomethane (TRIS), N-[tris[tris]-methyl]-2-aminoethanesulfonic acid (TES), TAPS, and N-tris-methyl]-3amino-2-hydroxypropanesulfonic acids (TAPSO), were studied by potentiometric measurements.
Abstract: The complexation equilibria of Fe(III) with two buffer families, which are ubiquitous in biological system studies, were studied by potentiometric measurements at a constant ionic strength of I = 0.1 mol·dm−3 NaNO3 in aqueous solutions at 298.15 K. The members of TRIS family are tris(hydroxymethyl)aminomethane (TRIS), N-[tris(hydroxymethyl)methyl]-2-aminoethanesulfonic acid (TES), N-[tris(hydroxymethyl)methyl]-3-aminopropanesulfonic acid (TAPS), N-[tris(hydroxymethyl)methyl]-3-amino-2-hydroxypropanesulfonic acid (TAPSO), and N-tris(hydroxymethyl)methyl-4-aminobutanesulfonic acid (TABS) buffers. The members of morpholine family are 4-morpholineethanesulfonic acid (MES), 4-morpholinepropanesulfonic acid (MOPS), 3-morpholino-2-hydroxypropanesulfonic acid (MOPSO), and 4-(N-morpholino) butanesulfonic acid (MOBS) buffers. The overall stability constants were determined from pH-metric data using the least-squares curve-fitting program HYPERQUAD 2008. Based on the best-fit results, the species formed at equilibrium are ML, ML2, ML2H−1, and ML3 in the systems with TRIS family buffers. The complex species ML, ML2, ML2H−1, and MLH−1 are formed in the MOPSO-containing system, while ML, ML2, and ML2H−1 are formed in the systems with MES, MOPS, and MOBS. The stabilities of the complexes fall in the order TABS > TRIS > TAPS > TAPSO > TES and MOBS > MOPS > MOPSO > MES for the TRIS family and morpholine families, respectively.
TL;DR: A catalytic highly diastereo- and enantioselective synthesis of 2,6-cis-substituted tetrahydropyran derivatives was realized using a one-pot sequential catalysis involving Henry and oxa-Michael reactions.
TL;DR: These compounds were evaluated for their acetylcholinesterase (AChE) inhibitory activity and 5-amino-2,7-bis(4-methoxyphenyl)-2,3-dihydrobenzo[b]thiophene-4,6-dicarbonitrile was found to be the most potent against AChE with IC50 4.16 μmol/L.
TL;DR: In this article, a methyl morpholinium-functionalized poly(ether sulfone) copolymer was prepared as a novel anion exchange membrane, which showed good hydrolytic, thermal, mechanical and chemical stabilities.
Abstract: A methyl morpholinium-functionalized poly(ether sulfone) (MM-PES) copolymer was prepared as a novel anion exchange membrane. The MM-PES polymer was synthesized by polycondensation between the morpholine-containing hydroquinone and bisphenol A with bis(4-fluorophenyl)sulfone, followed by methylation of the morpholine group. The membrane obtained from MM-PES showed an IEC of 0.90 meq/g with high hydroxide conductivity of 1.6 × 10−2 S/cm at r.t. and 7.9 × 10−2 S/cm at 80 °C. The methyl morpholinium-functionalized PES membrane also displayed good hydrolytic, thermal, mechanical and chemical stabilities.
TL;DR: In this paper, a database investigation confirmed the tendency of urea to form more rigid systems of hydrogen bonds in the plane of the N2CO moiety, thus forming layer structures with close complementarity of the donors and acceptors, whereas the more flexible sulfur acceptor of thiourea can also accept hydrogen bonds from donors that lie far from the N 2CS plane, forming three-dimensional packing patterns with much more variable parameters.
Abstract: The solvents 1,4-dioxane and morpholine have been employed to synthesize solvates of urea and thiourea. The structures confirm the tendency of urea to form more rigid systems of hydrogen bonds in the plane of the N2CO moiety, thus forming layer structures with close complementarity of the donors and acceptors, whereas the more flexible sulfur acceptor of thiourea can also accept hydrogen bonds from donors that lie far from the N2CS plane, forming three-dimensional packing patterns with much more variable parameters. A database investigation confirms these tendencies. The solvate urea:morpholine (1:1) crystallizes in Pbcm with Z = 4. The complete urea molecule lies in the mirror plane, as do the heteroatoms of the morpholine molecule. The molecular packing is a layer structure. The solvate urea:1,4-dioxane (1:1) crystallizes in P2/c with Z = 2. The CO bond of the urea molecule lies along a twofold axis, whereas the dioxane molecule lies across an inversion centre. The molecules form a layer structure analogous to that of the morpholine solvate. The thiourea solvates are more complex, and both involve a more irregular hydrogen bonding geometry at sulfur. The solvate thiourea:morpholine (4:3) crystallizes in P21/c with Z = 2. The asymmetric unit contains two independent molecules of thiourea, one morpholine on a general position, and one morpholine disordered over an inversion centre. The thiourea molecules combine to form an open framework with a series of channels, in which the morpholine molecules are attached. The solvate thiourea:1,4-dioxane (4:1) crystallizes in P21/n with Z = 2. The asymmetric unit contains two independent molecules of thiourea and one molecule of dioxane across an inversion centre. One thiourea molecule and the dioxane combine to form a layer structure. The second thiourea molecule links these layers in the third dimension.
TL;DR: In this paper, a diastereoselective intramolecular aza-Michael reaction between N-Cbz carbamates and enones was studied, and it was revealed that Bronsted acids with different strengths produce different diastereromers.
Abstract: A diastereoselective intramolecular aza-Michael reaction between N-Cbz carbamates and enones was studied. The investigation revealed that Bronsted acids with different strengths produce different diastereomers. The catalysts TfOH and TFA were used to generate differential outcomes in the aza-Michael reaction.
TL;DR: A pair of iridium-catalyzed regiospecific and stereospecific reactions of the carbonates of γ-hydroxy α,β-unsaturated esters were developed and a series of 3,4-disubstituted oxazolidin-2-ones were obtained by using allylamine as a nucleophile.
Abstract: A pair of iridium-catalyzed regiospecific and stereospecific reactions of the carbonates of γ-hydroxy α,β-unsaturated esters were developed. The reaction pathways are strongly affected by the choice of amines employed. A diverse range of γ-substituted α,β-unsaturated γ-amino esters were prepared in excellent yields with various amine nucleophiles such as benzylamine, diallylamine, morpholine, aniline and N-methylaniline. Substitution at the γ-position was well tolerated, encompassing alkyl, aryl and heteroaryl substituents. Enantioenriched (E)-α,β-unsaturated γ-amino esters could also be synthesized from the corresponding enantioenriched allylic carbonates with complete chirality transfer. In sharp contrast, a series of 3,4-disubstituted oxazolidin-2-ones were obtained by using allylamine as a nucleophile.
TL;DR: Most compounds except 22 were found to be active against Mycobacterium smegmatis, Candida albicans and/or Saccharomyces cerevisiae, while 9a and b, which are Mannich bases incorporating morpholine or piperazine nucleus, exhibited excellent antimicrobial activity on test microorganisms.
Abstract: Synthesis of the carbothioamides (5, 13, 22) was performed starting from 3H-1,2,4-triazol-3-ones (2, 17) by several steps, and then, these carbothioamides was converted to triheterocyclic compounds incorporating 1,2,4-triazole, imidazole and 1,3-thiazol(idinone) moieties. The reaction of compound 2 with 3,4-difluoronitrobenzene afforded the 2-(2-fluoro-4-nitrophenyl) derivative, 10. Compound 10 was converted to the arylideneamino derivatives (12a, b) via the reduction of nitro group. On the other hand, the treatment of the hydrazide (20) that was obtained starting from 17, with several aromatic aldehydes generated the corresponding arylidenhydrazides (21a–c). Mannich reaction between compound 2 and a suitable heterocyclic amine resulted in the N-alkylation of 2. All newly synthesized compounds were screened for their antimicrobial activities. In general, most compounds except 22 were Found (%) to be active against Mycobacterium smegmatis, Candida albicans and/or Saccharomyces cerevisiae. Furthermore, 9a and b, which are Mannich bases incorporating morpholine or piperazine nucleus, exhibited excellent antimicrobial activity on test microorganisms. In addition, the hydrazide, 4, was Found (%) to have activity towards Ec and Yp.
TL;DR: Preliminary antimicrobial susceptibility studies against five microorganisms show that the above triazine-based Ag-NHC complexes are active antimicrobial and antifungal agents.
Abstract: Convenient syntheses of mono- and bis-imidazolium 1,3,5-triazine derivatives bearing piperidine and morpholine substituents are reported. In situ deprotonation of the mono-imidazolium salts and reaction with Ag2O or Au(tht)Cl (tht = tetrahydrothiophene) precursors affords the corresponding Ag(NHC)Cl and Au(NHC)Cl carbene complexes. In the presence of Ag(I) or Au(I) salts the bis-imidazolium pincers eliminate the imidazolium group to afford –OMe or –NMe2 substituted triazines depending on the solvent used. In solution, the Ag(I) and Au(I) complexes show a barrier to rotation about the Ctriazine–Namine bonds, with calculated ΔG≠ barriers in the region of 70 kJ mol−1. Single crystal X-ray structures of several of the proligands and their corresponding Ag(I) and Au(I) complexes were obtained. These universally reveal an extended, rigidly planar π-conjugated network between the triazine core, imidazolium/imidazolylidene substituents and exocyclic amine functions, to which the origin of the rotational barrier observed in solution is attributed. Only very weak Ntriazine–metal interactions are observed in the solid state, as indicated by small deviations of the CNHC–Ag–Cl bond angles from 180° and also supported by DFT calculations on the Ag(NHC)Cl complex (NHC = 4,6-dipiperidinyl-2-methylimidazolylidene triazine). Preliminary antimicrobial susceptibility studies against five microorganisms (methicillin resistant Staphylococcus aureus NCTC 13277, S. aureus NCTC 6571, Pseudomonas aeruginosa NCTC 10662, Proteus mirabilis NCTC 11938 and Candida albicans ATCC 90028) show that the above triazine-based Ag-NHC complexes are active antimicrobial and antifungal agents.
TL;DR: In this paper, the HRh(CO)(PPh 3 ) 3 complex was encapsulated into the pores of amino functionalized hexagonal mesoporous silica and was characterized by physico-chemical techniques like P-XRD, 31 P-CPMAS NMR, FT-IR, SEM, ICP and N 2 adsorption analysis.
Abstract: HRh(CO)(PPh 3 ) 3 complex was encapsulated into the pores of amino functionalized hexagonal mesoporous silica. The catalyst was characterized by physico-chemical techniques like P-XRD, 31 P-CPMAS NMR, FT-IR, SEM, ICP and N 2 adsorption analysis. The catalyst was active for hydroaminomethylation and a variety of alkenes and amines were used as reactants for hydroaminomethylation. The catalyst afforded to achieve 100% conversion with high (>95%) selectivity to corresponding amines. Parametric variations were performed by taking 1-hexene and morpholine as representative reactants for the study of catalyst amount, temperature, pressure and 1-hexene:morpholine ratio. Significant amounts of aldehydes and enamines were observed during the course of the reaction indicating that there could be two possible rate determining steps. The catalyst was effectively recycled up to five times without much loss in its activity and selectivity.
TL;DR: In this article, a morpholine reaction set developed to simulate low-pressure flames was updated based on the current shock tube data, recently published rate constants for relevant reactions, and newly calculated thermochemistry.