Synthesis,structure and characterization of some Schiff bases bearing phenylferrocene

Some novel Schiff bases bearing phenylferrocene were synthesized by condensation reaction of 4‐ferrocenylaniline with different aromatic aldehydes. The compounds prepared were characterized by spectroscopic methods (IR, UV–visible, ¹H and ¹³C NMR) and elemental analysis. The single crystal analysis of compound F1 [monoclinic, space group, P2₁/c (no. 14), a = 19.858(2), b = 7.416(2), c = 12.095(5) Å, β = 106.257(14) ] indicates a trans imine bond with a bond length of 1.270(2) Å, typical of a carbon‐nitrogen double bond. Copyright © 2007 John Wiley & Sons, Ltd.     

Synthesis,characterization and antibacterial activity of some new pyrazole based Schiff bases

In the present study a series of new Schiff bases were synthesized. All the synthesized compounds were characterized by IR, ¹H NMR, mass spectral and elemental analyses. Newly synthesized compounds were screened for their antibacterial (Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa) activity. The results revealed that, compounds 3f and 3c have exhibited significant biological activity against the tested microorganisms.     

Synthesis,characterization and antibacterial activity of indium(III) complexes with adamantane-ring containing Schiff bases

Indium(III) chloride tetrahydrate and Schiff-base ligands derived from adamantaneamine and 3-/4-methoxysalicylaldehyde gave two complexes, C₂₂H₃₂Cl₃InN₂O₃ (1) and C₃₆H₄₄C_l3InN₂O₄ (2), respectively. The complexes were characterized by IR, ¹H NMR, elemental analysis, molar conductance, thermal analysis, and single-crystal X-ray diffraction. Complex 1 crystallizes in the monoclinic system, P2₁/n space group with the asymmetric unit consisting of one indium(III), one N-(3-methoxysalicylidene)-aminoadamantane (L¹), three chlorides and one N,N-dimethylformamide molecule. The indium is six-coordinate with reversed triangular-prism geometry via three oxygens and three chlorides. Complex 2 crystallizes in the triclinic system, P 1 space group; the asymmetric unit consists of one indium(III), two N-(4methoxysalicylidene)-aminoadamantane (L²), and three chlorides. The indium is five-coordinate with distorted trigonal-bipyramidal geometry via two oxygens and three chlorides. Antibacterial activities of the complexes have been investigated against Escherichia coli and Staphylococcus aureus.     

Synthesis,characterization and biological properties of novel ON donor bidentate Schiff bases and their copper(II) complexes

Four novel ON donor Schiff bases (E)-3-((4-phenoxyphenylimino)methyl)benzene-1,2-diol (HL₁),(E)-3-((4-(4-biphenyloxy)phenyliminomethyl)benzene-1,2-diol (HL₂), (E)-3-((4-naphthoxyphenylimino)methyl)benzene-1,2-diol (HL₃), (E)-3-((4-(2-naphthoxy)phenylimino)methyl)benzene-1,2-diol (HL₄) and their copper(II) complexes bis((E)-3-((4-phenoxyphenylimino)methyl)benzene-1,2-diol) copper(II) (Cu(L₁)₂) bis((E)-3-((4-(4-biphenyloxy)phenylimino)methyl)benzene-1,2-diol) copper(II) (Cu(L₂)₂), bis((E)-3-((4-naphthoxyphenylimino)methyl)benzene-1,2-diol) copper(II) (Cu(L₃)₂), bis((E)-3-((4-(2-naphthoxy)phenylimino)methyl)benzene-1,2-diol) copper(II) (Cu(L₄)₂) have been synthesized and characterized by spectroscopic (FTIR, NMR, UV–visible) and elemental analysis. The crystal structures of HL₁, HL₂, HL_3, and HL₄ have been determined, which reveal intramolecular N-H?O (HL₁, HL₂, HL_3, and HL₄) hydrogen bonds in the solid state. Keto-amine and enol-imine tautomerism is exhibited by the Schiff bases in solid and solution states. The Schiff bases and their copper(II) complexes have been screened for their biological activities. In antimicrobial assays (antibacterial and antifungal), HL₄ showed promising results against all strains through dual inhibition property while the rest of the compounds showed activity against selective strains. On the other hand, in cytotoxic, DPPH, and inhibition of hydroxyl (OH) free radical-induced DNA damage assays, the results were found significantly correlated with each other, i.e. the ligands HL₁ and HL₂ showed moderate activity while their complexes Cu(L₁)₂ and Cu(L₂)₂ exhibited prominent increase in activity. As the results of these assays are supporting each other, it represents the strong positive correlation and antioxidant nature of investigated compounds.     

Synthesis,characterization, electrochemistry and evaluation of biological activities of some ferrocenyl Schiff bases

Synthesis of ferrocenyl Schiff bases ( 1–6 ) was carried out by the condensation reaction of 4‐ferrocenyl aniline with different substituted aromatic aldehydes and acetyl acetone. Compounds were characterized by physical measurements, elemental analysis, FT‐IR, ¹H‐NMR and ¹³C‐NMR spectroscopy. Single crystal X‐ray analysis of compound 2 showed the co‐planarity of both aromatic rings connected by a C–N double bond. Compounds demonstrated reversible one‐electron redox behavior and their peak currents were found to increase linearly with the square root of the sweep rate ν^1/2. The overall electrode processes were found to be diffusion controlled. Compounds 1 and 4 showed low cytotoxicity and appreciable antifungal, antioxidant and DNA protection activities. Copyright © 2010 John Wiley & Sons, Ltd.     

Synthesis,characterization, thermal,and antimicrobial studies of binuclear metal complexes of sulfa-guanidine Schiff bases

A series of metal complexes of Schiff bases derived from condensation of sulfa-guanidine with 1-benzoylacetone (H₂L¹), 2-hydroxybenzophenol (H₂L²), dibenzoylmethane (H₂L³), 5-methylisatine (H₂L⁴), and 1-methylisatine (H₂L⁵) have been synthesized. The complexes are characterized by elemental analysis, molar conductance, magnetic moment measurements, IR, UV–Vis, ¹H NMR, and ESR spectra, as well as thermogravimetric analysis. The low molar conductance values indicate the complexes are nonelectrolytes. IR and ¹H NMR spectra show that H₂L¹–H₂L⁵ are coordinated to metal ions by two bidentate centers. Mn(II), Co(II), Ni(II), and Cu(II) complexes display paramagnetic behavior, whereas the Zn(II)-complex was diamagnetic. All studies confirm the formation of an octahedral geometry for [Cu₂L¹(AcO)₂(H₂O)₆] · 3H₂O (1), [Mn₂L⁴(AcO)₂(H₂O)₆] · 2H₂O (6), [Ni₂L⁴(AcO)₂(H₂O)₆] · 2H₂O (8), a tetrahedral geometry for [Cu₂L²(AcO)₂(H₂O)₂] (2), [Cu₂(L⁴)₂] (4), [Co₂(L⁴)₂] · 2H₂O (7) and [ZnHL⁴(AcO)(H₂O)] · 2H₂O (9) and a trigonal bipyramid geometry for [Cu₂L³(AcO)₂(H₂O)₄] (3) and [Cu₂HL⁵(AcO)₃(H₂O)₃] · H₂O (5). H₂L⁴ was most effective on Gram negative, Gram positive bacteria, and fungi (diameters inhibition zone ranged between 10.5–27.5 mm) after 24 and 48 h, respectively. Complex 8 showed moderate antimicrobial activity. Its minimum inhibitory concentration (MIC) against Escherichia coli, Bacillus subtilis, Candida albicans and Aspargllus flavas was 20 mg L^–1. The compound proved to be of moderate toxicity and its LD₅₀ was 20 mg L^–1.     

Hydrolysis study: Synthesis of novel styrenic Schiff bases derived from benzothiazole

Novel styrenic Schiff base derivatives of benzothiazole are synthesized. The condensation of 4-vinylbenzaldehyde 1 with either benzothiazol-2-amine or 4-methoxy-benzothiazol-2-amine leads to a mixture of two isomers. From 4-methyl-benzothiazol-2-amine and 6-fluoro-benzothiazol-2-amine, the N-(4-vinylbenzylidene)-4-methyl-benzothiazol-2-amine 8 and N-(4-vinylbenzylidene)-6-fluoro-benzothiazol-2-amine 9 are isolated, respectively. The structures of the synthesized Schiff bases are confirmed through a combination of various spectroscopic techniques including IR, UV, ¹H and ¹³C NMR. A kinetic study of the hydrolysis process of derivatives 6 and 9 in buffered aqueous medium at pH 4.4, 7.4 and 8.5 is conducted by UV spectroscopy. It is shown that the hydrolysis of these compounds is a first order reaction showing an increasing rate as the medium acidity is enhanced.     

Synthesis,characterization and cytotoxicity of platinum(II) complexes containing reduced amino acid ester Schiff bases

Nine platinum(II) complexes containing reduced amino acid ester Schiff bases were synthesized and characterized using spectroscopy (¹H NMR, ¹³C NMR, infrared), elemental analysis and molar conductivity. The interaction of these complexes with salmon sperm DNA was investigated by means of ultraviolet and circular dichroism spectroscopies. The potential antitumor activity of all compounds was tested in vitro on HeLa and A549 tumor cell lines. Almost all the complexes exhibited better cytotoxic activity than cisplatin against these cell lines.     

Synthesis,spectroscopic characterization,thermal behaviour,in vitro antimicrobial and anticancer activities of novel ruthenium tricarbonyl complexes containing monodentate V‐shaped Schiff bases

The interaction of Ru₃(CO)₁₂ with a novel family of monodentate V‐shaped Schiff base ligands (L^1–4; L¹: (E)‐1‐(4‐((4‐bromobenzylidene)amino)phenyl)ethanone, L²: (E)‐1‐(3‐(4‐(dimethylamino)benzylideneamino)phenyl)ethanone, L³: (E)‐1‐(4‐(4‐(dimethylamino)benzylideneamino)phenyl)ethanone, L⁴: (E)‐1‐(3‐(3,4‐dimethoxybenzylideneamino)phenyl)ethanone) in air under atmospheric pressure afforded the novel complexes [Ru(CO)₃(L^1–4)₂]. The parent ligands and their complexes were characterized using elemental analyses and spectroscopic techniques. In addition, the structure of the representative ligand L¹ was determined using single‐crystal X‐ray analysis. The stereochemistry and theoretical optimization of the three‐dimensional geometry of the ligands and their complexes were justified. In vitro antimicrobial screening against bacterial stains Escherichia coli and Staphylococcus aureus and fungus Candida albicans was conducted. Cytotoxicity of the compounds as anti‐tumour agents was evaluated against liver carcinoma (HepG2), breast carcinoma (MCF7) and colon carcinoma (HCT‐116) cell lines relative to cisplatin and doxorubicin. The complexes showed variable in vitro cytotoxic activities against the three studied cell lines, with IC₅₀ values less than those of cis‐platin, and thus appear to be building blocks for promising anti‐tumour agents.     

Novel aluminium compounds derived from Schiff bases: Synthesis,characterization and catalytic performance in hydroboration

Seven novel aluminium complexes supported by Schiff base ligands derived from o‐diaminobenzene or o‐aminothiophenol were synthesized and characterized. The reactions of AlMe₃ with L¹ (N,N′‐bis(benzylidine)‐o‐phenylenediamine) and L² (N,N′‐bis(2‐thienylmethylene)‐o‐phenylenediamine) gave the complexes L¹AlMe₃ ( 1 ) and L²AlMe₂ ( 2 ), respectively, which involved two types of reaction mechanisms: one was proton transfer and ring closure, and the other was alkyl transfer. Complexes L³AlMe₂ (HL³ = 4‐chlorobenzylidene‐o‐aminothiophenol) ( 3 ), L⁴AlMe₂ (HL⁴ = 2‐thiophenecarboxaldehyde‐o‐aminothiophenol) ( 4 ), L³AlH(NMe₃) ( 5 ), L⁴AlH(NMe₃) ( 6 ) and L⁵AlH(NMe₃) (HL⁵ = 4‐methylbenzylidene‐o‐aminothiophenol) ( 7 ) were prepared by reacting HL^3–5 with equimolar AlMe₃ or H₃Al?NMe₃, respectively. Compounds 3 – 7 feature an organic–inorganic hybrid containing CNAlSC five‐membered ring. All complexes were characterized using ¹H NMR and ¹³C NMR spectroscopy, X‐ray crystal structure analysis and elemental analysis. The efficient catalytic performances of 1 – 7 for the hydroboration of carbonyl groups were investigated, with compound 4 exhibiting the highest catalytic activity among all the complexes.     

New immobilized Schiff bases

In this study, three new immobilized Schiff bases and their Co(II), Cu(II) and Ni(II) metal complexes have been prepared. The ligands silica-Si[N-(3-propyl)2,4-dihydroxybenzaldimine] (1) H₂L, silica-Si[N-(3-propyl)4-methylsalicylaldimine-3-methoxy] (2) HL and silica-Si[N-(3-propyl)2-pyridinecarboxyaldimine] (3) L have bidentate characters. Therefore, the complexes are the mononuclear. Ligands and metal complexes were characterized by FTIR, AAS and thermoanalytical techniques. On the basis of analytical data and IR studies, a 1:1 metal to ligand stoichiometry has been suggested. TG and DTA results showed that these ligands and complexes had good thermal stability. The heat capacities of ligands were reported in the temperature range 273–363 K as no thermal anomaly was found in this temperature range.     

Synthesis of Schiff bases by condensation of hetarylcarboxaldehydes withp-phenetidine

Summary Treatment of quinolinecarboxaldehydes and their derivatives withp-ethoxyaniline yields in a one-step reaction a series of new Schiff bases in 47–73% yield. The products [quinoline-2-, 6-methylquinoline-2-, quinoline-4-, quinoline-8-, and acridine-9-N-(p-ethoxyphenyl)formimidoyl], have been fully characterized.

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Synthese von Schiffschen Basen durch Kondensation von Hetarylaldehyden mitp-Phenetidin

Zusammenfassung Umsetzung von Chinolinaldehyden und deren Derivaten mitp-Ethoxyanilin liefert in einer Einstufenreaktion neue Schiffsche Basen in 47–73%iger Ausbeute. Alle Produkte [Chinolin-2-, 6-Methylchinolin-2-, Chinolin-4-, Chinolin-8- und Acridin-9-N-(p-ethoxyphenyl)formimidoyl] wurden voll charakterisiert.

     

Synthesis,spectral characterization and biological studies of transition metal(II) complexes with triazole Schiff bases

New metal based triazoles (1–12) have been synthesized by the interaction of novel Schiff base ligands (L¹–L³) with the Co(II), Ni(II), Cu(II) and Zn(II) metal ions. The Schiff base ligands and their all metal(II) complexes have been thoroughly characterized using various physical, analytical and spectroscopic techniques. In vitro bacterial and fungal inhibition studies were carried out to examine the antibacterial and antifungal profile of the Schiff bases in comparison to their metal(II) complexes against two Gram‐positive, four Gram‐negative and six fungal strains. The bioactivity data showed the metal(II) complexes to have more potent antibacterial and antifungal activity than their uncomplexed parent Schiff bases against one or more bacterial and fungal species. Copyright © 2012 John Wiley & Sons, Ltd.     

The liquid crystalline properties of some ferrocene‐containing Schiff bases

The synthesis and characterization of new ferrocene‐containing mesomorphous compounds is described. In order to induce mesogenic behavior, the structure of the substituent was systematically modified. Derivatives with no more than two rings in the core did not exhibit liquid crystalline properties. The synthesized products were characterized using NMR, IR and mass spectroscopy, DSC and polarized optical microscopy. Copyright © 2007 John Wiley & Sons, Ltd.     

An approach to fused pyrimidine derivativesvia Schiff bases of aromaticortho-nitrocarbaldehydes. An investigation of substituent effects on the reaction course

The synthesis of fused pyrimidines from the Schiff bases of aromatic ortho-nitrocarbaldehydes is reported. The Schiff bases after selective reduction of the nitro group on 10% Pd/C, followed by condensation of the amines formed with orthoesters, are transformed to the corresponding imidates. Heating of the latter in a sealed tube with an excess of ammonia (or with ammonia in ethanol) gives fused pyrimidines. The influence of various substituents in the aromatic ring of the imine moiety of the Schiff bases on the overall yield of fused pyrimidine derivatives has been investigated. Moderate electron-withdrawing groups gave the best results.Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, PL-01-224 Warszawa, PolandTranslated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 799–805, June, 2000.     

Synthesis and antioxidant activities of Schiff bases and their complexes: a review

Schiff bases, named after Hugo Schiff , are aldehyde‐ or ketone‐like compounds in which the carbonyl group is replaced by imine or azomethine group. They are widely used for industrial purposes and also have a broad range of applications as antioxidants. An overview of antioxidant applications of Schiff bases and their complexes is discussed in this review. A brief history of the synthesis and reactivity of Schiff bases and their complexes is presented. Factors of antioxidants are illustrated and discussed. Copyright © 2016 John Wiley & Sons, Ltd.     

Synthesis,characterization and magnetostructural correlation studies on three binuclear copper complexes of pyrimidine derived Schiff base ligands

Three binuclear Cu(II) complexes of two pyrimidine derived Schiff base ligands, 2-S-methyl-6-methyl-4-formyl pyrimidine-N(4)-ethyl thiosemicarbazone (HL₁) and salicyl hydrazone of 2-hydrazino-4,6-dimethylpyrimidine (HL₂), have been prepared. HL₁ produces a bis(μ-thiolato) Cu(II) complex co-crystallizing with its mononuclear analog, [Cu₂(L₁)₂(NO₃)₂][Cu(L₁)(NO₃)] (1). On the other hand HL₂ shows versatility by producing two different classes of binuclear Cu(II) complexes, a bis(μ-phenoxo) complex [Cu₂(L₂)₂(NO₃)₂] (2) and another a (μ-4,4′-bipyridyl) complex, [Cu₂(L₂)₂(μ-4,4′-bipyridyl)(NO₃)₂] (3) under suitable conditions. All the three complexes show distorted square pyramidal geometry around each Cu atom but to a varied extent. Magnetic behavior of complex 1 shows that it is strongly ferromagnetic in nature whereas compounds 2 and 3 are weakly antiferromagnetic in nature. A magnetostructural correlation study combined with molecular modelling on complexes 1 and 2 has thrown light on the difference on magnetic interaction between the Cu atoms in these two complexes. Various factors that may be responsible for such differences are also explored. A novel and potentially useful pH dependant conversion of 3 to 2 has also been noticed.     

Solid-state synthesis of Schiff bases

A new preparative method for the synthesis of Schiff bases by the solid-state interaction of crystalline organic and organometallic aldehydes and amines is suggested. The possibility of direct synthesis of aldimines in the solid state from amine salts without isolation of the free amines is demonstrated. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2056–2059, November, 1997.     

Synthesis and smectogenic properties of novel phloroglucinol-based star-shaped liquid crystals containing three peripheral alkyloxylated Schiff base arms

A series of symmetrical trimeric liquid crystalline compounds of which the molecular structure with a central core of 1,3,5-benzene attached by three rod-like mesogenic Schiff base moieties via the propylene spacers and ether linkages has successfully been synthesised and characterised by infra red and nuclear magnetic resonance spectroscopic techniques. All the star-shaped compounds in this series exhibit predominantly SmC phase except the analogue possessing terminal C₈H₁₇ group. It is apparent that the members with even parity from C₁₀H₂₁ to C₁₆H₃₃ show enantiotropic SmC phase while the member with longest terminal chain of C₁₈H₃₇ is inclined to monotropic smectogen. The X-ray diffraction measurements reveal that the tilted smectic layer structures of the SmC phase are confirmed to have an obvious sharp peak at small angles of 2θ ～ 1.03°–1.48° with d-spacing values of 4.01–4.58 nm, which are corresponding to tilt angles of ～48° in the SmC phase.