scholarly journals Synthesis, Characterization, and Agricultural Biological Activities of 5-Fluoro-2-hydroxy Butyrophenone

2013 ◽  
Vol 2013 ◽  
pp. 1-5 ◽  
Author(s):  
Fengli Xin ◽  
Chunhua Du ◽  
Gongjia Lan ◽  
Zhuanping Wu

A novel synthetic approach towards 5-fluoro-2-hydroxy butyrophenone is reported. Using 4-fluorophenol as a raw material, the processes of etherification protection, Friedel-Crafts acylation and demethylation provide the target compound under mild conditions. The structure was characterized by the melting point and IR, MS,1H-NMR, and13C-NMR spectroscopy. The bioassay results indicate that the target compound exhibits potent antifungal activities againstValsa mali,Coniella dipodiella, and other agricultural plant fungi. The target compound also shows potent herbicidal activities forLactuca sativa, a dicotyledon, andEchinochloa crus-galli, a monocotyledon. The toxicity regression C50values of the compound againstValsa mali,Coniothyrium diplodiella,Lactuca sativaseedling, andEchinochloa crusgalliseedling were calculated by SPSS. The Hormesis effect for roots ofEchinochloa crusgalliwas confirmed.

2014 ◽  
Vol 618 ◽  
pp. 170-174
Author(s):  
Hong Qi Li ◽  
Xiu Juan Tian ◽  
Zhen Chen ◽  
Ding Xiao ◽  
Ning Fang ◽  
...  

A new coumarin-1,2,3-triazole diad was designed and synthesized by Pechmann-Duisberg reaction and click chemistry. The three-step synthetic route to the target compound afforded an overall yield of 56%. The structures of the synthesized compounds were characterized by 1H NMR, 13C NMR, IR and mass spectrum. The click chemistry provided an ideal approach for synthesis under mild conditions of coumarin-1,2,3-triazole diads which may exhibit excellent biological activities such as antitubercular activity.


2014 ◽  
Vol 2014 ◽  
pp. 1-7
Author(s):  
Gauri D. Bajju ◽  
Altaf Ahmed ◽  
Deepmala Gupta ◽  
Ashu Kapahi ◽  
Gita Devi

The synthesis and spectroscopic characterization of new axially ligated indium(III) porphyrin complexes were reported. Chloroindium(III) porphyrin (TPPIn-Cl) was obtained in good yield by treating the corresponding free base with indium trichloride. The action of the different phenols on chloroderivatives (TPPIn-Cl) led to the corresponding phenolato complexes (TPPIn-X). These derivatives were characterized on the basis of mass spectrometry,1H-NMR, IR, and UV-visible data. The separation and isolation of these derivatives have been achieved through chromatography. The spectral properties of free base porphyrin and its corresponding metallated and axially ligated indium(III) porphyrin compounds were compared with each other. A detailed analysis of UV-Vis,1H-NMR, and IR suggested the transformation from free base porphyrin to indium(III) porphyrin. Besides,13C-NMR and fluorescence spectra were also reported and interpreted. The stability of these derivatives has also been studied through thermogravimetry. The complexes were also screened for anticancerous activities. Among all the complexes, 4-MePhO-InTPP shows highest anticancerous activity. The title complexe, TPPIn-X (where X = different phenolates), represents a five-coordinate indium(III) porphyrin complex in a square-pyramidal geometry with the phenolate anion as the axial ligand.


2009 ◽  
Vol 2009 (4) ◽  
pp. 208-211 ◽  
Author(s):  
Jing Zhang ◽  
Lixue Zhang ◽  
Xinxiang Lei ◽  
Changfeng Zhou ◽  
Xiaodan Fu ◽  
...  

Sixteen novel Schiff's bases have been synthesised in high yields from 4-amino-3-(3-hydroxybutyl)-1 H-1, 2, 4-triazole-5-thione. All the newly synthesised compounds have been characterised by elemental analysis, IR, 1H NMR, 13C NMR and MS. Plant growth-regulating activity tests showed that most compounds have remarkable effects on the growth of wheat and radish at a mass concentration of 50μg mL−1.


2014 ◽  
Vol 2014 ◽  
pp. 1-16 ◽  
Author(s):  
Mohamed A. Riswan Ahamed ◽  
Raja S. Azarudeen ◽  
N. Mujafar Kani

Terpolymer of 2-amino-6-nitro-benzothiazole-ethylenediamine-formaldehyde (BEF) has been synthesized and characterized by elemental analysis and various spectral techniques like FTIR, UV-Visible, and1H and13C-NMR. The terpolymer metal complexes were prepared with Cu2+, Ni2+, and Zn2+metal ions using BEF terpolymer as a ligand. The complexes have been characterized by elemental analysis and IR, UV-Visible, ESR,1H-NMR, and13C-NMR spectral studies. Gel permeation chromatography was used to determine the molecular weight of the ligand. The surface features and crystalline behavior of the ligand and its complexes were analyzed by scanning electron microscope and X-ray diffraction methods. Thermogravimetric analysis was used to analyze the thermal stability of the ligand and its metal complexes. Kinetic parameters such as activation energy(Ea)and order of reaction (n) and thermodynamic parameters, namely,ΔS,ΔF,S*, andZ, were calculated using Freeman-Carroll (FC), Sharp-Wentworth (SW), and Phadnis-Deshpande (PD) methods. Thermal degradation model of the terpolymer and its metal complexes was also proposed using PD method. Biological activities of the ligand and its complexes were tested againstShigella sonnei,Escherichia coli,Klebsiellaspecies,Staphylococcus aureus,Bacillus subtilis, andSalmonella typhimuriumbacteria andAspergillus flavus,Aspergillus niger,Penicilliumspecies,Candida albicans,Cryptococcus neoformans,Mucor speciesfungi.


2011 ◽  
Vol 2011 ◽  
pp. 1-6 ◽  
Author(s):  
Shao Han Liao ◽  
Dai Hua Hu ◽  
Ai Ling Wang ◽  
De Peng Li

As core skeletons of lamellarins: 5,6-Dihydropyrrolo[2,1-a]isoquinolines are one of the important alkaloids that exhibit significant biological activities, in this study, an efficient synthetic route was described for two novel compounds, 5,6-dihydropyrrolo[2,1-a]isoquinolinesIandII. CompoundIwas synthesized from isovanillin with 28.3% overall yield by a six-step reaction whileIIfrom 2-(3,4-dimethoxyphenyl) ethanamine was with 61.6% overall yield by a three-step reaction. And the structures of these two compounds were confirmed by means of IR spectrum,1H NMR,13C NMR, MS, HRMS, and melting point measurements.


2014 ◽  
Vol 33 (2) ◽  
pp. 189 ◽  
Author(s):  
Mustafa Er ◽  
Ayşe Şahin ◽  
Hakan Tahtacı

<p>Thiosemicarbazone derivatives <strong>3a–e</strong> were synthesized by the reaction of various aldehydes<strong> 1a–e</strong> with 4-methyl thiosemicarbazide <strong>2</strong> in 78% to 90% yield. Then, the thiazole moieties of the target materials <strong>5a–e</strong> were obtained in high yields (71–93%) using the Hantzsch reaction utilizing thiosemicarbazone derivatives <strong>3a–e</strong> with ethyl-2-chloroacetoacetic ester. The substituted nitrile derivatives <strong>7a–e</strong> were obtained in moderate to high yield (58–84%) from the reaction of compounds <strong>5a–e</strong> with chloroacetonitrile by the nucleophilic aliphatic substitution reaction in the presence of anhydrous potassium carbonate. Finally, substituted 2-amino-1,3,4-thiadiazole compounds <strong>9a–e</strong> were obtained in moderate to good yields (51–62%) from the reaction of thiosemicarbazide with substituted nitrile derivatives <strong>7a–e</strong>. As a result, compounds that all share a high disposition for biological activities were obtained. The structures of the newly synthesized compounds were confirmed by IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, elemental analysis, and mass spectrometric techniques.</p>


2011 ◽  
Vol 236-238 ◽  
pp. 1914-1918
Author(s):  
Ru Lin Li ◽  
Lin Wang ◽  
Gang Xue

A novel compound N-benzoyl-N'-(4-chlorobenzamido) thiourea was prepared from benzoyl isothiocyanate which was obtained from benzoyl chloride and potassium thiocyanate, and 4-chlorobenzoyl hydrazine which was obtained from ethyl 4-chlorobenzoate and hydrazine hydrate. IR,1H NMR,13C NMR and elemental analysis were utilized to determine the structure of the thiourea. The biological tests indicated that the target compound had antibacterial activity against bacillus subtilis and taphylo-coccus aurers. Meanwhile, the thermal stability was investigated by thermogrativity(TG) and differential thermogrativity (DTG). The results demonstrated there was one weight-loss in the thermal decomposition process. The thermal kinetics equation obtained describing the thermal decomposition process was expressed as .


2018 ◽  
Vol 20 (2) ◽  
pp. 24-31 ◽  
Author(s):  
Joanna Paciorek-Sadowska ◽  
Marcin Borowicz ◽  
Bogusław Czupryński ◽  
Ewa Tomaszewska ◽  
Joanna Liszkowska

AbstractA new bio-polyol based on white mustard oil (Synapis alba) and 2,2′-mercaptodiethanol (2,2′-MDE) was obtained. The synthesis was carried out by two-step method. In the first stage, the double bond of the unsaturated fatty acid residues was oxidized, and in the second step the epoxy rings were opened with 2,2’-MDE. The properties of the obtained bio-polyol for application as raw material in polyurethane-polyisocyanurate foams (PUR-PIR) - hydroxyl number, acid number, density, viscosity, pH, water content, FTIR,1H NMR and13C NMR were investigated. Based on the obtained results, foaming formulations containing 0 to 0.6 R of the new bio-polyol were prepared. Significant impact of bio-polyol on apparent density, compressive strength, brittleness, flammability, water absorption and thermal conductivity of polyurethane composites were noted. Modified foam had better functional properties than reference foam e.g. lower brittleness, better thermal insulation properties and better fire resistance.


2019 ◽  
Vol 21 (1) ◽  
pp. 50-51
Author(s):  
Junyi Hu ◽  
Aiqiang Guo ◽  
Yingqian Xu ◽  
Changsheng Pan ◽  
Xingfu Wei ◽  
...  

Abstract α-Damascone is widely used in perfumes. However, the manufacture of α-damascone remains challenging owing to the limitations of current production processes. Herein, α-damascone was successfully synthesized from α-ionone using a new route involving only four steps, namely oximization, epoxidation, dehydration, and reduction. The total yield was 54.9% with a final chemical purity of 97% (by GC). Only water, cyclohexane, and ethanol were used in the reactions except in the purification step, and all solvents could be recycled. The structures of the intermediates and target compound were identified by 1H NMR and 13C NMR analyses and MS experiments. This route is a simple and successful method for the industrial preparation of α-damascone.


2018 ◽  
Vol 42 (9) ◽  
pp. 471-473
Author(s):  
Shanwen Chen ◽  
Peiming Zhang ◽  
Huali Chen ◽  
Pu Zhang ◽  
Yu Yu ◽  
...  

An improved and efficient method for the synthesis of panobinostat was developed. The commercially available starting material 4-(chloromethyl)benzaldehyde was converted to ( E)-methyl 3-[4-(chloromethyl)phenyl]acrylate via the Wittig–Horner reaction and was then directly condensed with 2-(2-methyl-1 H-indol-3-yl)ethanamine to afford the key intermediate ( E)-methyl 3-[4-({[2-(2-methyl-1 H-indol-3-yl)ethyl]amino}methyl)phenyl]acrylate in a one-pot synthesis reactor. Subsequently a nucleophilic substitution reaction was carried out smoothly to generate the desired compound. The key intermediate and target compound were characterised by HRMS, 1H NMR and 13C NMR. This procedure is operationally simple and would be more suitable for industrial production.


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