فهرست مطالب

Organic Chemistry Research
Volume:2 Issue: 2, Summer 2016

  • تاریخ انتشار: 1395/06/11
  • تعداد عناوین: 12
  • Leila Mahdavian * Pages 102-112

    Polycyclic aromatic hydrocarbons (such as, anthracene, benzo[a]pyrene and so on) are non-polar, hydrophobic compounds, which are not ionized. They are only slightly soluble in water. They are very dangerous compounds in the environment. The single-walled carbon nanotube (SWNT) is used for removal and conversion of anthracene to low-risk products. In this study, electron transfer between anthracene and SWNT (8,8) is evaluated through density functional approach at the level of B3LYP/6-31G. The calculation of the electronic properties shows that SWNT is very sensitive to the presence of anthracene molecule. The HOMO/LUMO and gap energy (Eg) changes were considerable. According to the calculated thermodynamic parameters through the DFT method, it is expected that SWNT be a candidate in the elimination of anthracene as well as a gas sensor for its detection and conversion. Regarding the thermodynamic results, the absorption of pollutant on nano-surface of SWNT is exothermic and spontaneous. The results show that the pollutant can be reduced or eliminated from the environment by single-walled carbon nanotubes.

    Keywords: Polycyclic aromatic hydrocarbons (PAHs), SWNT (8, 8), Density of states (DOSs), Computational Methods
  • Morteza Shiri *, Atefeh Nejatinejhad Arani, Zeynab Faghihi, Suhas A. Shintre, Neil A. Koorbanally Pages 113-119

    Vilsmeier Several diamide derivatives containing 2-chloroquinoline scaffolds were synthesized via Ugi reaction of 2-chloroquinoline-3-carboxaldehydes, amines, carboxylic acids and isocyanides. The diversity of these quinolinyl Ugi-adducts was increased by using 2-chloroquinoline-3-carboxylic acids as a source of acid. Among them, compounds 2d, 2n, 2p, 4a, 4c and 4e displayed moderate to good antibacterial and antifungal activity.

    Keywords: Multicomponent condensation, Quinolines, Diamides, antibacterial, Antifungal
  • Mohsen Khezri, Arash Afghan *, Laya Roohi, MohammadMehdi Baradarani Pages 120-126

    Vilsmeier-Haack reaction of 2,3,3-trimethyl-3H-benzo[g]indole, then aqueous basic work-up, leads to benzo[g]indol-2-ylidene- malondialdehydes. These react with various arylhydrazines and quinolin-2-ylhydrazine to form 3,3-dimethyl-2-(1-aryl-1H-pyrazol-4-yl)- 3H-benzo[g]indoles in good yields.the formula is not displayed correctly!

    Keywords: Vilsmeier-Haack reaction, Formylation, Pyrazole, Malondialdehyde, 2-Quinolylhydrazine, Arylhydrazine
  • Farzaneh Mohamadpour, Malek Taher Maghsoodlu *, Reza Heydari, Mojtaba Lashkari Pages 127-133

    An efficient and simple one-pot approach for the synthesis of 3,4-dihydropyrimidin-2-(1H)-one derivatives using antimony trichloride (SbCl3) as a mild catalyst by means of three-component Biginelli reaction between β-keto esters, aldehyde derivatives and urea/thiourea under thermal and solvent-free conditions with excellent yields and short reaction times is reported. This methodology offers several merits such as excellent yields, short reaction times, efficient, eco-friendly, solvent-free conditions, materials available, and simple operational procedure with no column chromatographic separation. The products are characterized by melting points and 1H NMR spectroscopy.

    Keywords: Antimony trichloride (SbCl3), 4-Dihydropyrimidinone, Multi-component synthesis, Biginelli reaction
  • Javad Safari, Majid Ahmadzadeh, Zohre Zarnegar * Pages 134-139

    In the present study, an attempt has been made to synthesize 3-methyl-4-arylmethylene isoxazole-5(4H)-one derivatives through sonication of hydroxylamine hydrochloride, ethyl acetoacetate and benzaldehyde derivatives in the presence of imidazole as a novel and effective catalyst in aqueous media. This green reaction under ultrasound irradiation has advantageous compared to conventional procedures in view of its shorter reaction times, high isolated yields, avoidance of using organic solvents, simple experimental procedure and workup and energy conservation. A combination of the advantages of ultrasound irradiation, homogeneous catalyst and aqueous media provides an important methodology for carrying out catalytic transformations.

    Keywords: Isoxazoles, Ultrasound irradiation, Imidazole, Catalyst, Water
  • Meghdad Karimi, Athar Nakisa, Kobra Azizi *, Akbar Heydari Pages 140-147

    We have used tungestophosphoric acid to catalyze oxidative amidation reaction from benzyl alcohols and methylarens with hydrochloride salts of amines. To achieve this purpose, modified magnetic nanoparticles (γ-Fe2O3@SiO2@H3PW12O40) were applied as catalyst and TBHP as external oxidant. After optimizing, different derivates of benzamides were synthesized in good yields. Also, the result of two oxidative amidation reactions was compared.

    Keywords: Oxidative amidation, Amid, Magnetic nanoparticles, Catalytic reaction
  • HabibOllah Foroughi *, Ali Khalafi Nezhad Pages 148-161

    The silica boron sulfuric acid nanoparticles (SBSANs) as an efficient heterogeneous solid acid catalyst with both Brønsted and Lewis acidic sites catalyzed the preparation of bis-4-hydroxycoumarin derivatives using reaction of aldehydes and 4-hydroxycoumarin under mild and solvent-free condition at room temperature. This new and efficient methodology has advantages in comparison with currently used methods such as: easy work-up, simple separation of catalyst from the reaction mixture, reusability and lower catalyst loading, relatively short reaction time, eco-friendly with environment, excellent yields, simple purification of products and mild reaction condition. Using this method a range of biologically active bis-4-hydroxycoumarin derivatives were synthesized in good to excellent yield. The catalyst system was reusable at least for 5 times in this reaction without significant decreasing in its catalytic activity.

    Keywords: Silica boron-sulfuric acid nanoparticles (SBSANs), Solid acid, Lewis-protic acid, Biscoumarin
  • Sobhan Rezayati *, Zahra Abbasi, Eshagh Rezaee Nezhad, Rahimeh Hajinasiri, Shahin Soleymani Chalanchi Pages 162-171

    A simple and facile method for the preparation ofFe2+ supported on hydroxyapatite-core-shell-γ-Fe2O3 nanoparticles (γ-Fe2O3@HAp-Fe2+ NPs) as an environmentally friendly and recyclable green catalyst is described and used for the one-pot synthesis of benzimidazoles and benzoxazole derivatives via reactions between aromatic aldehydes and ortho‐phenylenediamine or ortho‐aminophenol in aqueous media conditions at room temperature. This green method offers significant advantages in terms of its simplicity, very low loading of catalyst, high catalytic efficiency, good to excellent product yields, short reaction time, simple experimental and work-up procedure. Also, after the reaction, γ-Fe2O3@HAp-Fe2+ NPs can be easily recovered and reused for at least ten runs. This magnetic nanoparticle was characterized by Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscope (SEM) and vibrating sample magnetometry (VSM) spectra.

    Keywords: γ-Fe2O3@HAp-Fe2+ NPs, Lewis acid, Magnetic nanoparticle, Benzimidazole, Benzoxazole
  • Reza Ranjbar Karimi *, Fahimeh Bahadornia, Alireza Poorfreidoni Pages 172-176

    Some amide derivatives have been synthesized by the reaction of corresponding nitriles with potassium tert-butoxide as a nucleophilic oxygen source under ultrasonic irradiation. This new methodology provides good to excellent yields in short reaction times (15-90 min) at room temperature.

    Keywords: Ultrasound irradiation, Amide, Nitrile, Synthesis, Room tempereture
  • Mona Hosseini Sarvari *, Golnaz Parhizgar Pages 177-191

    Epoxides undergo regioselective ring opening with various nucleophiles using catalytic amount of nano magnesium oxide and water as solvent under mild reaction conditions. The remarkable features of this method are improved yields, high regioselectivity, and green chemistry agreement.

    Keywords: Nano MgO, Ring Opening, Epoxides, 2-Diols, 2-Substituted diols
  • Motahareh Irani, Reza Ranjbar Karimi *, Hamzeh Izadi Pages 192-196

    Some oxime ether derivatives of α-ionone (4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one) have been synthesized. Reaction of 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-ketoxime with various chloro and fluoro aromatic and hetero aromatic compounds gave the corresponding oxime ether derivatives via aromatic nucleophilic substitution (SNAr). The structures of these compounds were elucidated by IR, 1H NMR, 19F NMR and 13C NMR spectroscopic methods. All the compounds were screened in vitro against the common pistachio psylla, Agonoscena pistaciae, fifth instar nymphs. Results showed that compound 3c (LC50 value of 227.76 mg l-1) was much more toxic to fifth instar nymphs ofcommon pistachio psylla than compound 3a (LC50 = 1539.14 mg l-1) and compound 3f (LC50 = 569.319 mg l-1).the formula is not displayed correctly!

    Keywords: Oxime ether, pesticide, Synthesis, Ultrasonic irradiation, Agonoscena pistaciae
  • Zahra Kordrostami * Pages 197-207

    In this work, SO3H-functionalizedphthalimide (SFP) as a SO3H-containing solid acid is prepared by the reaction of phthalimide with chlorosulfonic acid, and characterized by FT-IR, 1H and 13C NMR, Mass, TG, DTG, XRD and SEM. Then, it is utilized as a highly efficient, heterogeneous and green catalyst for the one-pot multi-component condensation of dimedone with arylaldehydes, β-ketoesters and ammonium acetate under solvent-free conditions to afford polyhydroquinolines in excellent yields and in short reaction times.

    Keywords: SO3H-functionalized phthalimide (SFP), SO3H-containing solid acid, Dimedone, Arylaldehyde, β-Ketoester, Polyhydroquinoline