Synthesis of some 3-functionally substituted 2-pyrazolines

Reaction of the complex of 1-phenyl-3-pyrazolidone and phosphorus oxychloride with nucleophilic agents (amines and thiophenol) leads to the formation of 3-functionally substituted 2-pyrazolines.M. V. Lomonosov Moscow State University, Moscow, 119899. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp, 1494–1498, November, 1995. Original article submitted September 18, 1995.     

Synthesis and characterization of some novel 1,3-diaryl pyrazole bearing 2-oxopyridine-3,5-dicarbonitrile derivatives

Russian Journal of General Chemistry - A series of new 1-{[1-(3-chlorophenyl)-3-(4-methoxyphenyl)-1H-pyrazol-4-yl]methyleneamino}-6-amino-1,2-dihydro-4-(substitutedphenyl)-2-oxopyridine-3,5-di...     

Synthesis of 3-thienyl substituted 2-pyrazolines by 1,3-dipolar cycloaddition

1,3,5-Trisubstituted 3-thienylpyrazolines have been prepared in high yields by the reaction of substituted,N-(P;-nitrophenyl)-3-thiophenecarbohydrazonoyl chlorides with Et₃N in CH₂Cl₂ in the presence of an excess of a monosubstituted olefin. The reaction probably occurs as 1,3-dipolar cycloaddition of the corresponding 3-thiophenecarbonitrile imines formedin situ at the double bond of the olefin.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 114–117, January, 1994.     

Synthesis, characterization and fluorescent property evaluation of 1,3,5-triaryl-2-pyrazolines

A series of 1,3,5-triaryl-2-pyrazolines was synthesized by dissolving the corresponding 4-alkoxychalcones in glacial acetic acid containing a few drops of concentrated hydrochloric acid. This step was followed by the addition of (3,4-dimethylphenyl) hydrazaine hydrochloride. Finally the target compounds were precipitated by pouring the reaction mixture onto crushed ice. The structures of the synthesized compounds were established by physicochemical and spectroscopic methods. The 1,3,5-triaryl-2-pyrazolines bearing homologous alkoxy groups were found to possess fluorescence properties in the blue region of the visible spectrum when irradiated with ultraviolet radiation. The fluorescent behavior of these compounds was studied by UV-Vis and emission spectroscopy, performed at room temperature.     

Synthesis and spectral-luminescence properties of 1-(4′-formylphenyl)-3,5-diaryl-2-pyrazolines

It was demonstrated by means of the IR and PMR spectra that 1-phenyl-3,5-diaryl-2-pyrazolines that contain a grouping with a strong electron-acceptor effect, viz. a 4-nitrophenyl or 4-naphthalanhydride group or a 1,8-naphthoylene-1,2-benzimidazole fragment, in the 3 position undergo Vilsmeier formylation, like unsubstituted 1,3,5-triphenyl-2-pyrazoline, in the para position of the 1-phenyl ring. An investigation of the spectral-luminescence properties of the synthesized 1-(4-formylphenyl)-3,5-diaryl-2-pyrazolines showed that the introduction in the 1-phenyl ring of an electron-acceptor aldehyde group, which is inferior with respect to its acceptor effect to the groupings in the 3 position of the heteroring, does not change the nature of the long-wave absorption band. Substantial hypsochromic and hypsofluoric effects as compared with the corresponding 1-phenyl-unsubstituted compounds are noted in the electronic spectra of these compounds.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 807–811, June, 1982.The authors thank I. D. Kalikhman for recording the PMR spectra.     

Synthesis,characterization, pyrolysis kinetics and conductivity studies of chloro substituted cobalt phthalocyanines

Cobalt(II) phthalocyanine (CoPc), cobalt(II) tetrachloro phthalocyanine (CoPcCl₄), cobalt(II) octachloro phthalocyanine (CoPcCl₈) and cobalt(II) hexadecachloro phthalocyanine (CoPcCl₁₆) are synthesized pure and characterized using elemental analysis, UV-visible, IR-spectroscopy, magnetic susceptibility, X-ray crystallography, and thermogravimetry. All four complexes have monoclinic structure with different crystal lattice constants. Broido's, Coats-Redfern and Horowitz-Metzger relations were employed to calculate the kinetic and activation parameters associated with thermal decomposition of the above complexes. The compounds are analyzed for kinetic parameters, activation energies for decomposition and the Arrhenious pre-exponential factors, in their pyrolysis. Using these factors and standard equations, thermodynamic parameters such as enthalpy, entropy and free energies are calculated. The activation energies are evaluated based on their electrical conductivity conducted over the temperature range 30–200°C. The electrical conductivities observed at 30°C are in the order CoPcCl₁₆?>?CoPcCl₄?>?CoPcCl₈?>?CoPc. The relevant electrical conductivity data are reported.     

Synthesis and Antimicrobial Activities of Some 1-[(N,N-Disubstitutedthiocarbamoylthio)acetyl]-3,5-diaryl-2-pyrazolines

The increasing clinical importance of drug-resistant fungal and bacterial pathogens has lent additional urgency to microbiological research and new antimicrobial compound development. For this purpose, new pyrazoline derivatives were synthesized and evaluated for antimicrobial activity.

Some 1-[(N, N-disubstitutedthiocarbamoylthio)acetyl]-3,5-diaryl-2-pyrazolines derivatives were synthesized by reacting 1-(chloroacetyl)-3,5-diaryl-2-pyrazolines with appropriate potassium salts of secondary amine dithiocarbamic acids. The chemical structures of the compounds were elucidated by IR, ¹ H-NMR, and FAB⁺-MS spectral data. Their antimicrobial activities against Staphylococcus aureus (B-767), Escherichia coli (B-3704), Pseudomonas aeruginosa (ATCC 27853), Proteus vulgaris (NRLL B-123), and Candida albicans (NRRL-27077) were investigated. The results showed that some of the compounds have notable activity against S. aureus and C. albicans.     

Enantioselective synthesis of bio-relevant 3,5-diaryl pyrazolines

The straightforward asymmetric construction of bio-relevant Δ(2)-pyrazolines having either N-(thio)amide or N-acetyl functional groups and flanked by aryl substituents such as phenol at C3 and C5 has been achieved through an enantioselective phase transfer organocatalytic addition of N-Boc hydrazine to chalcones followed by a transprotection sequence allowing N-Boc transformation into N-CXNHR (X = S, O) or N-Ac functional groups. This approach was applied to a straightforward elaboration of chiral monoamine oxidase inhibitor derivatives.     

Synthesis and solid-state fluorescence of 2-alkylamino-4-aminopyridine-3,5-dicarbonitriles

Reactions of 4-amino-2-aryl-6-chloropyridine-3,5-dicarbonitriles with primary and secondary amines afforded 2-alkylamino-4-amino-6-arylpyridine-3,5-dicarbonitriles which showed solid-sate fluorescence in the violet or blue region with the emission maxima in the λ range 400–460 nm.     

Synthesis, characterization and fluorescence studies of novel bi-phenyl based acrylate and methacrylate

4-[(1E)-3-(biphenyl-4-yl)buta-1,3-dien-1-yl]phenyl prop-2-enoate (ACH) and 4-[(1E)-3-(biphenyl-4-yl)buta-1,3-dien-1-yl]phenyl 2-methylprop-2-enoate (MCH) was synthesized from biphenyl in three steps and their structures were confirmed by elemental analysis, IR, NMR (1H, 13C, DEPT135, 1H-1H COSY, 1H-13C HSQC and 1H-13C HMBC) spectroscopic techniques. In this present study, various physicochemical characteristics we demonstrate solubility, color, absorbance and fluorescence property of novel biphenyl based acrylate and methacrylate measured in different solvents like benzene, dichloromethane, tetrahydrofuran, acetonitrile, dimethylsulfoxide and ethanol.     

Reactions of 4-phenyl-1,2,4-triazoline-3,5-dione with 2-pyrazolines

4-Phenyl-1,2,4-triazoline-3,5-dione (PTAD) acts as an efficient Michael acceptor in reactions with 1-unsubstituted 2-pyrazolines, giving substituted (3,5-dioxo-4-phenyl-1,2,4-triazol-idin-1-yl)-1-pyrazolines in quantitative yields. Through elimination of molecular nitrogen, the latter are easily transformed into the corresponding cyclopropanes. A reaction of methyl 5-methyl-2-pyrazoline-5-carboxylate with a twofold excess of PTAD leads to an intermediate bisadduct, which undergoes dediazotization to form a 1,3,5-triazabicyclo[3.3.0]octane-2,4-dione derivative. 1-Substituted 2-pyrazolines also add to PTAD with the exception that the 2-pyrazoline structure is retained in the product because of the migration of the C(3)H proton to PTAD.     

Synthesis,spectral characterization,and biological studies of 3,5-disubstituted-1,3,4-oxadiazole-2(3H)-thione derivatives

The reaction of 3,4-dichlorophenyl-1,3,4-oxadiazole-2( 3H )-thione with piperidine derivatives via Mannich reaction was used to generate eleven novel compounds in moderate to good yields. Synthesized molecules were characterized according to their structure with ¹H NMR, ¹³C NMR and FT-IR spectral foundations, which were compatible with literature informations. Antimicrobial activity and cytotoxicity studies were done by disc diffusion and NCI-60 sulphordamine B assay methods. The antimicrobial test results revealed that synthesized compounds have better activity against gram-positive species than gram-negative ones. A total analysis of the antibacterial, antifungal, and antiyeast activity revealed that newly synthesized compounds were really active against Bacillus cereus , Bacillus ehimensis, and Bacillus thuringiensis species . For cytotoxicity, among three different cancer cell lines (HCT116, MCF7, HUH7) compounds 5c, 5d, 5e, 5f, 5g, 5i, 5j and 5k were seemed especially effective on HUH7 cancer cell line via moderate to good activity. More significantly, against liver carcinoma cell line (HUH7) most of the compounds of the series ( 5c-5g and 5i-5j ) have better IC₅₀ values (IC₅₀= 18.78 µM) than 5-Florouracil (5-FU) and also compound 5d possessed 10.1 µM value, which represents good druggable cytotoxic activity. Further, the molecules were also screened for in silico chemoinformatic and toxicity data to gather the predicted bioavailibity and safety measurements.     

Synthesis and antimicrobial activity of quinoline-based 2-pyrazolines

A series of 2-pyrazolines was prepared in a reaction of quinolinylchalcones with phenyl hydrazine under both conventional and microwave-induced heating. Structures of the synthesized compounds were characterized by spectroscopic data and CHN analyses. All prepared compounds were tested for antimicrobial activity against bacterial strains, viz. Staphylococcus aureus, Salmonella typhii, Escherichia coli, and Shigella dysentery. Almost all synthesized compounds have shown antimicrobial activity; however, compounds with a chloro group as a substituent have been found to be more effective.     

微波辅助合成1,3-二苯基-2-吡唑啉

以取代苯肼盐酸盐(1)和β-二甲胺基苯丙酮盐酸盐(2)为原料, 在微波辐射条件下一步合成了一系列1,3-二苯基吡唑啉类化合物3. 本方法具有操作简单、反应时间短、产率高等特点.     

芳基取代咪唑衍生物的合成及其紫外、荧光性质研究

设计合成了两种新颖的三芳基咪唑类化合物5和6,研究了其反应机理,优化了环合加成反应的工艺条件,化合物经FT-IR、HMR和MS进行结构表征。研究了两个化合物在不同溶剂中的紫外与荧光光谱,发现官能苄基的引入,会使吸收峰和发射峰均有不同程度的蓝移,这些光谱性质为今后研究其双光子吸收、双光子荧光和非线性光学性质奠定了实验基础。     

单核镥取代的砷钨酸盐的合成、结构及表征

以双缺位结构钨酸盐K_(14)[As_2W_(19)O_(67)(H_2O)]为多酸前驱体与LuCl_3·6H_2O和2,6-吡啶二羧酸在常规水溶液中反应,制得了一例单核镥夹心的砷钨酸盐稀土衍生物K_8H_3[Lu(H_2O)_2(As_2W_(19)O_(67))(H_2O)]·39H_2O(1),并通过X射线单晶衍射、红外光谱、热重分析等方法对该化合物进行了测试和表征.X射线单晶衍射分析表明,化合物1属于单斜晶系,P-1空间群,晶胞参数a=1.253 54(9)nm,b=1.757 83(13)nm,c=2.111 40(16)nm,α=73.326 0(10)°,β=85.721 0(10)°,γ=89.856 0(10)°.该聚阴离子是由一个镥离子镶嵌在[As_2W_(19)O_(67)(H_2O)]~(14-)({As_2W_(19)})阴离子的缺位处构成的;热重分析结果表明,化合物1阴离子结构在400℃以内是对热稳定的.     

Synthesis,characterization, and fluorescence phenomena of 1‐naphthoxy and 1‐naphthylamino substituted cyclotriphosphazenes

The reactions of hexachlorocyclotriphosphazene N₃P₃Cl₆ ( 1 ) with 1‐naphthol and 1‐naphthylamine have been examined. The reaction of 1 with sodium 1‐naphthoxy gave the hexakis(1‐naphthoxy)cyclotriphosphazene ( 2 ) in high yield. Geminal 2,2‐di(1‐naphthylamino)‐4,4,6,6‐tetrachlorocyclotriphosphazene ( 3 ) was obtained from the reaction of 1 with 1‐naphthylamine. The structures of phosphazene derivatives were defined by elemental analysis, FTIR, UV‐‐visible, and ¹H, ¹³C, ³¹P NMR spectroscopy. The fluorescence intensity of the compounds was measured in THF and CH₂Cl₂. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:158–162, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20400     

Synthesis and characterization of asymmetric substituted dicarbamates

Several new asymmetric substituted dicarbamates were synthesized with a convenient route.Firstly,tolylene-2,4-diisocyanate dimmer was obtained from monomer with tributylphosphine as catalyst.Then,the dimmer reacted with alcohol(R~1OH) to prepare carbamate substituted uretidione.Finally,uretidione ring was opened and the released isocyanate reacted with another alcohol (R~2OH,R~1≠R~2).