Synthesis and antimicrobial activity of novel fused [1,2,4]triazino[5,6-<Emphasis Type="Italic">b</Emphasis>]indole derivatives

Synthesis of new fused systems of triazino[5,6-b]indole starting with preparation of 3-amino[1,2,4]-triazino[5,6-b]indole 1 by reaction of isatin with 2-aminoguanidinium carbonate in boiling acetic acid is presented [1]. Intermediate compound 1 reacted with aldehyde, ethyl chloroformate, triethyl orthoformate, and ninhydrine and gave new heterotetracyclic nitrogen systems, such as 3-(N ²-guanidinylimino)indole-2(1H)-one 2, 3-(N-ethoxycarbonylamino)-4H-[1,2,4]triazino[5,6-b]indole 3, 3-(N-ethoxymethyleneamino)-4H-[1,2,4]-triazino[5,6-b]indole 4, 3-(hydrazinothiocarbonylamino)-4H-[1,2,4]triazino[5,6-b]indole 5, respectively. N-(1,3-dioxoindene-2-ylidene)-4H-[1,2,4]triazino[5,6-b]indol-3-amine 6 was synthesized by reaction of compound 1 with aldehyde, ethyl chloroformate, triethyl orthoformate, and ninhydrine. New fused indole systems, pyrimido[2′,1′:3,4][1,2,4]triazino[5,6-b]indol-3(4H)-one 8, 9, 11, 12 and 1H-imidazo[2′,1′:3,4][1,2,4]triazino-[5,6-b]indol-2(3H)-one 10, were synthesized in the reaction of the intermediate 1 with bifunctional compounds. Structures of the products were elucidated from their elemental analysis and spectral data (IR, ¹H and ¹³C NMR and mass spectra). Antimicrobial activity of some synthesized compounds was tested.     

Crystal and molecular structure of 3,5-dimethyl-1<Emphasis Type="Italic">H</Emphasis>-pyrazolide of 3-O-acetyl ursolic acid

3,5-Dimethyl-1H-pyrazolide of 3-O-acetyl ursolic acid (II) is obtained in the course of the interaction of 3 O-acetyl ursolic acid acyl chloride (I) and 3,5-dimethyl-1H-pyrazole. The crystal structure of compound II is determined from the single crystal XRD data (150 K, Bruker X8 Apex CCD autodiffractometer, MoK _α radiation). The crystals are rhombic, the unit cell parameters are as follows: a = 10.6034(2) Å, b = 12.4096(2)Å, c = 24.5972(5)Å, P2₁2₁2₁ space group. The structure consists of discrete acentric molecules. When pyrazolide II is boiled in the alcohol alkali solution, secondary hydroxyl is deacetylated and 3,5-dimethyl-1H-pyrazolide of ursolic acid IV is formed. Compounds II and IV are studied by NMR spectroscopy.     

Microwave-assisted synthesis of 1-{2-[(1-benzyl-1<Emphasis Type="Italic">H</Emphasis>-1,2,3-triazol-4-yl)methoxy]phenyl}-3-(3-aryl-1-phenyl-1<Emphasis Type="Italic">H</Emphasis>-pyrazol-4-yl)prop-2-en-1-ones and their antimicrobial activity

A series of new (E)-1-{2-[(1-benzyl-1H-1,2,3-triazol-4-yl)methoxy]phenyl}-3-(3-aryl-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-ones (3a–3i) has been synthesized via copper-catalyzed 1,3-dipolar azide-alkyne cycloaddition reaction (CuAAC) of benzyl azide with substituted (E)-3-(3-aryl-1-phenyl-1H-pyrazol-4-yl)-1-[2-(prop-2-ynyloxy)phenyl]prop-2-en-1-ones (2a–2i). The synthesized compounds have been characterized by their IR, ^lH, ¹³C NMR spectra, and mass spectroscopy data. All the compounds have been screened for antimicrobial activity.     

Thermal and acid-catalyzed transformations of 3<Emphasis Type="Italic">H</Emphasis>-pyrazoles obtained from diphenyldiazomethane and methyl phenylpropiolate

Reaction of diphenyldiazomethane with methyl phenylpropiolate in diethyl ether alongside the expected methyl triphenyl-3H-pyrazole-4-and-5-carboxylates (I and II) (38 and 24%) gave rise also to 8% of methyl 3,5-diphenyl-1-(1-ethoxyethyl)-1H-pyrazole-4-carboxylate. The main thermolysis product obtained from 4-methoxy-carbonyl derivative I was methyl 1,3,5-triphenyl-1H-pyrazole-4-carboxylate, whereas from regioisomer II formed predominantly methyl 4,4,5-triphenyl-4H-pyrazole-3-carboxylate and 1-methoxycarbonyl-2,3,3-triphenylcyclopropene that was a minor product of 3H-pyrazole I thermolysis. Addition of concn. H₂SO₄ to the solutions of methyl triphenyl-3H-pyrazole-4-and-5-carboxylates in AcOH resulted in fast regioselective isomerization of the 3H-pyrazole derivatives into the corresponding 4H-pyrazoles.     

Synthesis of 4-halo-3-(phenylamino)furo[3,4-<Emphasis Type="Italic">c</Emphasis>]pyridin-1(3<Emphasis Type="Italic">H</Emphasis>)-ones

A method was developed for the synthesis of 4-halo-3-(phenylamino)-furo[3,4-c]pyridin-1(3H)-ones by the reaction of 4-halo-3-hydroxyfuro[3,4-c]pyridin-1(3H)-ones with aniline at room temperature.     

Synthesis and crystal structures of tetraacetylethylenediamine and <Emphasis Type="Italic">N</Emphasis>-(2-ammoniumethyl)carbamate

Two ethylenediamine derivatives—N-(2-ammoniumethyl)carbamate HN(COO^?)CH₂CH₂N⁺H₃ (I) and tetraacetylethylenediamine (H₃CC(O))₂NCH₂CH₂N(C(O)CH₃)₂ (II) (synthesized for the first time)—have been synthesized and characterized by X-ray crystallography. Compounds I and II are isolated as minor admixtures upon an attempt to synthesize ethylenediamine complexes of lanthanum and neodymium nitrates, respectively. The crystals of I and II are monoclinic: a = 7.778 Å, b = 8.060 Å, c = 7.568 Å, β = 95.73°, Z = 4, space group P2₁/c (I); a = 5.946, b = 10.255, c = 9.343 Å, β = 95.72°, Z = 2, space group P2₁/c (II). The bond lengths and bond angles lie within the corresponding standard values. Compounds I and II have different conformations of the N-C-C-N ethylenediamine moiety: gauche in I and trans in II, and the corresponding torsion angles are equal to 66.6° and 180°, respectively.     

Kumada cross coupling reaction based synthesis,antimicrobial and computational studies of 6-aryl-2-phenyl-3-methylquinazolin-4(3<Emphasis Type="Italic">H</Emphasis>)-ones

Nickel catalyzed Kumada cross coupling reaction, a novel synthetic method for the synthesis of 6-aryl-2-phenyl-3-methylquinazolin-4(3H)-ones (6a–6i), was carried out by condensing 6-iodo-2-phenyl-3-methyl-quinazolin-4(3H)-one (4) with various 6-aryl/heteroaryl Grignard reagents. Molecular properties of compounds 4 and 6a–6i were studied using semiempirical PM3 computational method. The optimized geometry of the product 6 indicated that the aryl group at the position 6 was not coplanar with respect to either quinazolinone ring or phenyl group at 2 position. Compounds 6a–6i were screened for their activity against bacteria and fungi.     

The role of substituents in a bidentate <Emphasis Type="Italic">N</Emphasis>,<Emphasis Type="Italic">N</Emphasis>-chelating ligand on the substitution of aqua ligands from mononuclear Pt(II) complexes

The rate of substitution of aqua ligands from three mononuclear platinum(II) complexes, namely [Pt{2-(pyrazol-1-ylmethyl)pyridine}(H₂O)₂](ClO₄)₂, [Pt(H ₂ Py)]; [Pt{2-(3,5-dimethylpyrazol-1-ylmethyl)pyridine}(H₂O)₂](ClO₄)₂, [Pt(dCH ₃ Py)] and [Pt{2-[(3,5-bis(trifluoromethyl)pyrazoly-1-ylmethyl]pyridine}(H₂O)₂](ClO₄)₂, [Pt(dCF ₃ Py)] by thiourea, N,N-dimethylthiourea and N,N,N′,N′-tetramethylthiourea, was studied in aqueous perchloric acid medium of constant ionic strength. The substitution reactions were investigated under pseudo-first-order conditions as a function of nucleophile concentration and temperature using UV/Visible and stopped-flow spectrophotometries. The observed pseudo-first-order rate constants, \( k_{{{\text{obs }}\left( {1/2} \right)}} \), for the stepwise substitution of the first and second aqua ligands obeyed the rate law: \( k_{{{\text{obs}}\left( {1/2} \right)}} = k_{{2 \left( { 1 {\text{st/2nd}}} \right)}} \left[ {\text{Nu}} \right] \). The first substitution reaction takes place trans to the pyrazole ligand, while the second entering nucleophile is stabilised at the reaction site trans to the pyridine ligand. The rate of substitution of the first aqua ligand from the complexes followed the order: Pt(dCF ₃ Py) > Pt(H ₂ Py) > Pt(dCH ₃ Py), while that of the second was Pt(H ₂ Py) ≈ Pt(dCF ₃ Py) > Pt(dCH ₃ Py). Lower pK _a values were found for the deprotonation of the aqua ligand cis to the pyrazole ring. Density functional theory calculations were performed to support the interpretation of the experimental results.     

Pure aromatic hydrocarbons with <Emphasis Type="Italic">meta</Emphasis>-linked phenyl-core and perihedral fluorene substitutions with/without inert groups of <Emphasis Type="Italic">tert</Emphasis>-butyl: bipolar hosts for blue phosphorescence

Two pure hydrocarbon molecules of 1,3,5-tris(9-phenyl-9H-fluoren-9-yl)benzene (m TPFB) and 1,3,5-tris(2-tert-butyl-9-phenyl-9H-fluoren-9-yl)benzene (t Bu-m TPFB) were synthesized. Due to the conjugation blocked connection mode and rigid/bulky substitutions, these two materials possess high triplet energy, enabling them as good hosts for blue phosphor in PhOLEDs. By studying their thermal, electrochemical, electronic absorption and photoluminescent properties, it was found that the influence of the inert tert-butyl group on material photoelectrical properties is negligible. For instance, m TPFB and t Bu-m TPFB showed very similar absorption and emission profiles, with almost the same bandgap, triplet energy and energy levels. However, the encapsulation of tert-butyl on the 2-position of 9-phenylfluorene enhanced material thermal stability. Most importantly, carrier transport properties were improved dramatically, as proved by the mono carrier device. Blue phosphorescent OLEDs hosted by t Bu-m TPFB showed external quantum efficiency of 15.2% and current efficiency of 23.0 cd/A, which were much higher than that of the OLEDs based on m TPFB with the analogous structure.     

Hyperconjugative interactions are the main responsible for the anomeric effect: a direct relationship between the hyperconjugative anomeric effect,global hardness and zero-point energy

The correlations between the global hardness (η), hyperconjugative anomeric effect, Pauli exchange-type repulsions, electrostatic model associated with dipole–dipole interaction and structural parameters in 2-fluorotetrahydropyran, -thiopyran, -selenopyran (1–3) and their chloro- (4–6) and bromo-analogs (7–9) were investigated by means of the conventional and range-corrected functionals and natural bond orbital (NBO) interpretation. By deletion of the HC-exo-AE and HC-endo-AE, the equatorial conformations of compounds 1–9 become more stable than their corresponding axial forms, revealing that anomeric relationships in compounds 1–9 have the hyperconjugative anomeric effect origins while the electrostatic model associated with dipole–dipole interaction does not play a determining role on the variations of the anomeric relationships in these compounds. The anomeric relationships in compounds 1–3 have no Pauli exchange-type repulsions origin, but it has a significant impact on the conformational preferences in compounds 4–6 and 7–9. A canonical molecular orbital interpretation was conducted to investigate the correlations between the linear combinations of natural bond orbitals in the HOMOs, LUMOs and the global hardness (η) values. There is a direct relationship between the hyperconjugative anomeric effect, global hardness (η) and zero-point energies in compounds 1–3, 4–6 and 7–9. The harder axial conformations with the greater hyperconjugative anomeric effect and zero-point energy values are more stable than their corresponding equatorial forms.     

Structural systematics and conformational analyses of an isomer grid of nine tolyl-<Emphasis Type="Italic">N</Emphasis>-pyridinylcarbamates

A 3 × 3 isomer grid of nine Methylphenyl-N-pyridinylcarbamates (CxxM) is reported with seven CxxM crystal structures at 294 K (xx = pp, pm, po, mp, op, om, oo; x = para-, meta-, ortho), where Cx = pyridinyl ring (as C₅NH₄NH-) and xM is representative of –C(=O)OC₆H₄CH₃. All seven carbamate crystal structures aggregate via N–H…N intermolecular interactions with the three CpxM carbamates having C(6) zigzag chains, CmpM with C(5) zigzag chains and three ortho-pyridine CoxM structures as hydrogen-bonded dimers with graph set \(R_{2}^{2}\) (8) and augmented by flanking C–H…O contacts. The CpoM crystal structure crystallises with 0.25 CHCl₃ per carbamate molecule and solvent channels aligning along the a-axis direction. Conformational analyses of the nine minimised CxxM structures in gas phase are detailed for comparisons with the solid-state structures and demonstrate similarities between both structural methods. The modelling results also demonstrate the problems associated with pendant ortho-groups sterically clashing in the CmoM and CooM structures and methods to find a reasonable estimate of the CxxM conformational landscape.     

Isomeric form and proton localization in (9<Emphasis Type="Italic">E</Emphasis>)-phenanthrene-9,10-dione[(1<Emphasis Type="Italic">Z</Emphasis>)-3,3-dimethyl-3,4-dihydroisoquinolin-1(2<Emphasis Type="Italic">H</Emphasis>)-ylidene]hydrazonium bromide

(9E)-Phenanthrene-9,10-dione[(1Z)-3,3-dimethyl-3,4-dihydroisoquinolin-1(2H)-ylidene]hydrazonium bromide (LH)Br (I) was synthesized. The models of protonated forms of the LH⁺ cation were calculated by quantum-chemical methods, and their relative stability was estimated. The crystal structure of compound I was determined by X-ray diffraction analysis. Compound I is built according to the cation-anion type (the mobile protons are located at the nitrogen atoms). The cation exists in the s-cis,cis-isomeric form stabilized by two cyclic hydrogen bonds. The π-electron density is localized on the multiple bonds N(1)-C(1) (1.292(4) Å) and N(3)-C(12) (1.294(4) Å). the spectroscopic characteristics (IR and electronic absorption spectra) of compound I are obtained.     

Features of self-organization of highly dilute solutions of (<Emphasis Type="Italic">S</Emphasis>)-, (<Emphasis Type="Italic">R</Emphasis>)-, and (<Emphasis Type="Italic">SR</Emphasis>)-methionines and related carbamides and glycolurils

Aqueous solutions of (S)-, (R)-, and (SR)-methionines (1–3); carbamide (4); (S)-, (R)-, and (SR)-N-carbamoylmethionines (5–7); glycoluril (8); and glycolurils containing (S)and (R)-methionine moieties (9 and 10) kept under natural and hypoelectromagnetic conditions were studied in comparison by a complex of physicochemical methods (dynamic and electrophoretic light scattering, conductometry, pH-metry, and dielcometry). The process of selforganization and the properties of dilute solutions (1.0?10^–15–10^–1 mol L^–1) of compounds 1–10 was shown for the first time to depend substantially on the structure of the solute and configuration of methionine (Met) enantiomers. In the series 1–3, the greatest ability to self-organization is observed for solutions of (SR)-Met in which supramolecular domains (1.0?10^–5–1.0?10^–1 mol L^–1) and nanoassociates (1.0?10^–11–1.0?10^–8 mol L^–1) are formed. The formation of nanoassociates in a concentration range of 1.0?10^–12–1.0?10^–6 mol L^–1 can be responsible for the appearance of nonmonotonic concentration dependences of the physicochemical properties of solutions of N-carbamoylmethionines 5–7, whereas the physicochemical properties are more pronounced in solution of (S)-N-carbamoylmethionine 5 than in solutions of 6 and 7. The strongest influence of the configuration of the Met enantiomer on the ability of solution to self-organization was revealed in a series of glycolurils 9, 10: solutions of 9 with the (S)-Met moiety are disperse systems in which nanoassociates are formed in a range of 1.0?10^–15–1.0?10^–5 mol L^–1, whereas in solutions of 10 with the (R)-Met fragment the ability to self-organization in the low-concentration range is absent.     

Synthesis and antimicrobial screening of novel 9-{2-[(1<Emphasis Type="Italic">H</Emphasis>-1,2,3-triazol-4-yl)methoxy]phenyl}-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1<Emphasis Type="Italic">H</Emphasis>-xanthene-1,8(2<Emphasis Type="Italic">H</Emphasis>)-dione derivatives

A series of novel 9-{2-[(1H-1,2,3-triazol-4-yl)methoxy]phenyl}-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione derivatives were synthesized by a click chemistry approach. The structures of all the newly synthesized compounds were characterized by IR, MASS, ¹H and ¹³C NMR spectral data. The final analogues showed good to excellent antibacterial and antifungal activities in an agar well diffusion assay. Compounds 6i and 6f were the most active against all the test bacterial and fungal strains.     

Synthesis and structure elucidation of some new azo dye from hydroxyquinolin-2(<Emphasis Type="Italic">1H</Emphasis>)-one derivatives and their antimicrobial evaluation

The aim of the work is synthesis of some novel azo dye from 1,2-dihydro-4-hydroxy-2-oxoquinoline-6-sulfonic acid (3), 4-hydroxy-6-methoxyquinolin-2(1H)-one (4), and 4-hydroxy-6-nitroquinolin-2(1H)-one (5). The prepared compounds were screened for antibacterial against Staphylococcus aureus, Escherichia coli, and antifungal activity against Candida sp., Aspergillus multi and Aspergillus niger. The structure of newly compounds was characterized by ¹H-NMR, IR and elemental analysis.     

Synthesis and characterization of half-sandwich ruthenium(II) complexes with N-alkyl pyridyl-imine ligands and their application in transfer hydrogenation of ketones

A series of new arene ruthenium(II) complexes were prepared by reaction of ruthenium(II) precursors of the general formula [(η⁶-arene)Ru(μ-Cl)Cl]₂ with N,N′-bidentate pyridyl-imine ligands to form complexes of the type [(η⁶-arene)RuCl(C₅H₄N-2-CH=N-R)]PF₆, with arene = C₆H₆, R = iso-propyl (1a), tert-butyl (1b), cyclohexyl (1c), cyclopentyl (1d) and n-butyl (1e); arene = p-cymene, R = iso-propyl (2a), tert-butyl (2b). The complexes were fully characterized by ¹H NMR and ¹³C NMR, UV–Vis and IR spectroscopies, elemental analyses, and the single-crystal X-ray structures of 2a and 2b have been determined. The single-crystal molecular structure revealed both compounds with a pseudo-octahedral geometry around the Ru(II) center, normally referred to as a piano stool conformation, with the pyridyl-imine as a bidentate N,N ligand. The activity of all complexes in the transfer hydrogenation of cyclohexanone in the presence of NaOH and iso-propanol is reported, the compounds showing turnover numbers of close to 1990 and high conversions. Complex 2b was also shown to be very effective for a range of aliphatic and cyclic ketones, giving conversions of up to 100 %.     

Glycosylation of panaxadiol

Glycosylation of 3β,12β-dihydroxy-20R,25-epoxydammarane (panaxadiol) (1) under Koenigs–Knorr, Helferich, and ortho-ester reaction conditions was studied. Condensation of panaxadiol and 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosylbromide (2) in the presence of silver oxide and 4-Å molecular sieves in dichloroethane gave a mixture of acetylated panaxadiol 3- and 12-O-β-D-glucopyranosides (3:1 ratio). Reaction of diol 1 and D-glucose tert-butylorthoacetate (3) in the presence of 2,4,6-collidinium perchlorate in chlorobenzene resulted in regioselective formation of panaxadiol 12-O-β-D-glucopyranoside tetraacetate. Reaction of equimolar amounts of 1 and glycosyl donor 2 in the presence of Hg(II) cyanide in nitromethane at 90°C was accompanied by opening of the tetrahydropyran ring and gave 3β,12β,25-trihydroxydammar20(22)E-ene 12-O-β-D-glucopyranoside tetraacetate. Panaxadiol 3- and 12-O-β-D-glucopyranosides and 3β,12β,25-trihydroxydammar-20(22)E-ene 12-O-β-D-glucopyranoside tetraacetate were synthesized for the first time.     

Synthesis,structure, and stereochemical non-rigidity of bis[(2,2-dimethyl-4-oxo-2<Emphasis Type="Italic">H</Emphasis>-benzo[<Emphasis Type="Italic">e</Emphasis>][1,3]oxazin-3(4<Emphasis Type="Italic">H</Emphasis>)-yl)methyl] dichlorosilane and -germane

Bis[(2,2-dimethyl-4-oxo-2H-benzo[e][1,3]oxazin-3(4H)-yl)methyl]dichlorosilane (1) and -germane (2) were synthesized by the reaction of 2,2-dimethyl-3-(trimethylsilyl)-2H-benzo[e][1,3]oxazin-3(4H)-one with bis(chloromethyl)dichlorosilane and -germane, respectively, taken in a ratio of 2 : 1. The structures of these compounds were determined and their stereodynamic behavior in solution was studied by multinuclear (¹H, ¹³C, and ²⁹Si) and twodimensional (¹H, ¹³C COSY, HETCOR) NMR spectroscopy. The ²⁹Si NMR spectroscopic study of a solution of complex 1 provides evidence that the silicon atom in this complex is pentacoordinate. The X-ray diffraction study showed that the germanium atom in complex 2 in the solid state is hexacoordinate. The permutation isomerization in the coordination units of complexes 1 and 2 was found and investigated by dynamic ¹H NMR spectroscopy. Different mechanisms of stereodynamic transformations are suggested and discussed.     

Lanthanide contraction effect on the crystal structures of 2D lanthanide coordination polymers based on 2-(trifluoromethyl)-1<Emphasis Type="Italic">H</Emphasis>-imidazole-4,5-dicarboxylic acid

A series of new two-dimensional (2D) lanthanide(III) coordination polymers, namely {[Ln₂(μ ₂-HTFMIDC)₃(DMA)₄] · 2H₂O} _n [Ln = Pr (1); Nd (2); Sm (3); Eu (4); H₃TFMIDC = 2-(trifluoromethyl)-1H-imidazole-4,5-dicarboxylic acid, DMA = N,N′-dimethylacetamide] for type I and {[Ln₂(μ ₂-HTFMIDC)₃(DMA)₂(H₂O)₂] · DMA} _n [Ln = Eu (5); Gd (6)] for type II, have been successfully prepared under solvothermal conditions and structurally characterized for the first time. Both two types of structures exhibit similar 2D honeycomb-like networks, which are constructed by the linkages of μ ₂-HTFMIDC^2? bis-(bidentate) bridging ligands and Ln(III) metal centers. However, slightly different ABAB stacking fashions of the 2D layers and distinctly different hydrogen bonding interactions between the neighboring 2D layers are observed in crystal structures of type I and type II, which may be attributed to the lanthanide contraction effect. Meanwhile, the solid-state luminescent properties of 4 and 5 have been also investigated.     

Synthesis and crystal structure of (1<Emphasis Type="Italic">H</Emphasis>-Benzo[<Emphasis Type="Italic">d</Emphasis>]imidazol-2-yl)(3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)methanone (L). complex formation of copper(II) and cobalt(II) chlorides with L

(1H-Benzo[d]imidazol-2-yl)(3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)methanone (L) and its complexes with copper and cobalt chlorides [CuLCl₂] (I) and [CoLCl₂] (II) are synthesized and studied by IR spectroscopy. The structure of molecule L is determined by X-ray diffraction analysis. Molecule L crystallizes as a cis-trans isomer. The dihydroisoquinoline (A) and benzimidazole (B) fragments lie in the mutually perpendicular planes. The N-C bond lengths of fragment A (double bond N(1)-C(1) 1.278(3) Å, ordinary bond N(1)-C(9) 1.490(3) Å) differ noticeably. The N-C bond lengths in fragment B range from 1.327(4) to 1.389(4) Å. The C=O bond is 1.218(3) Å According to the data of IR spectroscopy and X-ray diffraction analysis, complexes I and II are assumed to have different structures with different coordination modes to the metal atom of molecule L: through the imine atoms N(1) and N(2) of fragments A and B in I and through the N(1) atom of the dihydroisoquinoline fragment and the O atom of the carbonyl group in II.