Iranian Chemical Society
Organic Chemistry Research
2383-242X
2
2
2016
09
01
Computational Chemistry of Anthracene (PAH) Removal by SWNT Nano-filters: DFT
102
112
EN
Leila
Mahdavian
Doroud Branch, Islamic Azad University, P.O. Box: 133. Doroud. Iran
mahdavian_leila@yahoo.com
10.22036/org.chem..2016.14116
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 (E<sub>g</sub>) 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.
Polycyclic aromatic hydrocarbons (PAHs),SWNT (8,8),Density of states (DOSs),Computational Methods
https://www.orgchemres.org/article_14116.html
https://www.orgchemres.org/article_14116_2fb1f2d5496510ba138cd6db5e6e7173.pdf
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2
2
2016
09
01
Synthesis and Biological Evaluation of Novel Quinoline Derivatives as Antibacterial and Antifungal Agents
113
119
EN
Morteza
Shiri
0000-0003-2908-3471
Alzahra University
mshiri@alzahra.ac.ir
Atefeh
Nejatinejhad-Arani
Zeynab
Faghihi
Suhas A.
Shintre
Neil A.
Koorbanally
10.22036/org.chem..2016.14694
Vilsmeier Several diamide derivatives containing 2-chloroquinoline scaffolds were synthesized <em>via</em> 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 <strong>2d, 2n, 2p, 4a, 4c </strong>and<strong> 4e</strong> displayed moderate to good antibacterial and antifungal activity.
Multicomponent condensation,Quinolines,Diamides,antibacterial,Antifungal
https://www.orgchemres.org/article_14694.html
https://www.orgchemres.org/article_14694_0fd624655cb72999f2f6451e54172632.pdf
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2
2
2016
09
01
Vilsmeier-Haack Reaction with 2,3,3-Trimethyl-3H-benzo[g]indole and Its Conversion into 2-(1-aryl-1H-pyrazol-4-yl)-3,3-dimethyl-3H-benzo[g]indoles
120
126
EN
Mohsen
Khezri
Department of Organic Chemistry, Faculty of Chemistry, University of Urmia, Urmia 57153-165, Iran
m.khezri2013@gmail.com
Arash
Afghan
Urmia University of Technology, Urmia, Iran
a.afghan@che.uut.ac.ir
Laya
Roohi
Department of Organic Chemistry, Faculty of Chemistry, University of Urmia, Urmia 57153-165, Iran
laia.roohi@yahoo.com
Mohammad Mehdi
Baradarani
Department of Organic Chemistry, Faculty of Chemistry, University of Urmia, Urmia 57153-165, Iran
mmbaradarani@yahoo.com
10.22036/org.chem..2016.14824
Vilsmeier-Haack reaction of 2,3,3-trimethyl-3<em>H</em>-benzo[<em>g</em>]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-1<em>H</em>-pyrazol-4-yl)- 3<em>H</em>-benzo[<em>g</em>]indoles in good yields.
Vilsmeier-Haack reaction,Formylation,Pyrazole,Malondialdehyde,2-Quinolylhydrazine,Arylhydrazine
https://www.orgchemres.org/article_14824.html
https://www.orgchemres.org/article_14824_22e2019f87556f9db5a498c7ae9b8bbe.pdf
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2
2
2016
09
01
An Efficient Synthesis of 3,4-Dihydropyrimidin-2-(1H)-one Derivatives Promoted by Antimony Trichloride under Thermal and Solvent-free Conditions
127
133
EN
Farzaneh
Mohamadpour
Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran
mohamadpoor.f.7@gmail.com
Malek Taher
Maghsoodlu
Sistan &amp; Baluchestan University, Zahedan, IRAN
mt_maghsoodlou@yahoo.com
Reza
Heydari
Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran
heydari@hamoon.usb.ac.ir
Mojtaba
Lashkari
Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran
mojtaba_chem_84@yahoo.com
10.22036/org.chem..2016.14892
An efficient and simple one-pot approach for the synthesis of 3,4-dihydropyrimidin-2-(1<em>H</em>)-one derivatives using antimony trichloride (SbCl<sub>3</sub>) 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 <sup>1</sup>H NMR spectroscopy.
Antimony trichloride (SbCl3),3,4-Dihydropyrimidinone,Multi-component synthesis,Biginelli reaction
https://www.orgchemres.org/article_14892.html
https://www.orgchemres.org/article_14892_8e4c06b2464d3c3f778157e5ac178677.pdf
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2
2
2016
09
01
Ultrasound-assisted Method for the Synthesis of 3-Methyl-4-arylmethylene Isoxazole-5(4H)-ones Catalyzed by Imidazole in Aqueous Media
134
139
EN
Javad
Safari
Laboratory of Organic Chemistry Research, Department of Organic Chemistry, College of Chemistry, University of Kashan, 87317-51167 Kashan, I.R, Iran
safar_jav@yahoo.com
Majid
Ahmadzadeh
Laboratory of Organic Chemistry Research, Department of Organic Chemistry, College of Chemistry, University of Kashan, 87317-51167 Kashan, I.R, Iran.
m.ahmadzade85@gmail.com
Zohre
Zarnegar
University of Kashan
z_zarnegar@yahoo.com
10.22036/org.chem..2016.15347
In the present study, an attempt has been made to synthesize 3-methyl-4-arylmethylene isoxazole-5(4<em>H</em>)-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.
Isoxazoles,Ultrasound irradiation,Imidazole,Catalyst,Water
https://www.orgchemres.org/article_15347.html
https://www.orgchemres.org/article_15347_5f4c0968fb8652baf9cccd9809011d62.pdf
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2
2
2016
09
01
Tungstophosphoric Acid Supported on Silica-encapsulated γ-Fe2O3 Nanoparticles Catalyzed Oxidative Amidation
140
147
EN
Meghdad
Karimi
Tarbiat Modares University-Tehran_Iran
meghdadkarimi1365@gmail.com
Athar
Nakisa
Tarbiat Modares University-Tehran_Iran
athar_nakisa@yahoo.com
Kobra
Azizi
Tarbiat Modares University-Tehran, Iran
azizikobra@ymail.com
Akbar
Heydari
Tarbiat Modares University-Tehran_Iran
heydar_a@modares.ac.ir
10.22036/org.chem..2016.15519
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-Fe<sub>2</sub>O<sub>3</sub>@SiO<sub>2</sub>@H<sub>3</sub>PW<sub>12</sub>O<sub>40</sub>) 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.
Oxidative amidation,Amid,Magnetic nanoparticles,Catalytic reaction
https://www.orgchemres.org/article_15519.html
https://www.orgchemres.org/article_15519_d81b7d3a9d31e9bb581795c2e5804808.pdf
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2
2
2016
09
01
Synthesis of Bis-4-hydroxycoumarins via a Multi Component Reaction Using Silica Boron-sulfuric Acid Nanoparticles (SBSANs) as an Efficient Heterogeneous Solid Acid Catalyst
148
161
EN
Habib Ollah
Foroughi
Department of scince, Islamic AZad University, Fasa branch
foroughihabib@ymail.com
Ali
Khalafi-Nezhad
Department of Chemistry, Shiraz University, Shiraz,71454, I.R.Iran
khalafi@chem.susc.ac.ir
10.22036/org.chem..2016.15543
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.
Silica boron-sulfuric acid nanoparticles (SBSANs),Solid acid,Lewis-protic acid,Biscoumarin
https://www.orgchemres.org/article_15543.html
https://www.orgchemres.org/article_15543_af8aad6b543e55d6533701e9cf79babf.pdf
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2
2
2016
09
01
Fe2+ Supported on Hydroxyapatite-core-shell-γ-Fe2O3 Nanoparticles as an Inexpensive and Magnetically-recoverable Catalyst for Rapid Synthesis of Benzimidazoles and Benzoxazole Derivatives
162
171
EN
Sobhan
Rezayati
Islamic Azad University
sobhan.rezayati@yahoo.com
Zahra
Abbasi
Chemistry Department, College of Science Shahid Chamran University, Ahvaz, Iran
zahra.abbasi886@gmail.com
Eshagh
Rezaee Nezhad
Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran
e.rezaee66@yahoo.com
Rahimeh
Hajinasiri
Chemistry Department, Qaemshahr Branch, Islamic Azad University, P.O. Box 163, Qaemshahr, Iran
rhmhajinasiri@yahoo.com
Shahin
Soleymani Chalanchi
1Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran
sol.shahin@yahoo.com
10.22036/org.chem..2016.15544
A simple and facile method for the preparation ofFe<sup>2+</sup> supported on hydroxyapatite-core-shell-γ-Fe<sub>2</sub>O<sub>3</sub> nanoparticles (γ-Fe<sub>2</sub>O<sub>3</sub>@HAp-Fe<sup>2+</sup> 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-Fe<sub>2</sub>O<sub>3</sub>@HAp-Fe<sup>2+</sup> 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.
γ-Fe2O3@HAp-Fe2+ NPs,Lewis acid,Magnetic nanoparticle,Benzimidazole,Benzoxazole
https://www.orgchemres.org/article_15544.html
https://www.orgchemres.org/article_15544_f83d3d8bc33a5f0a31faf7c4d29da071.pdf
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2
2
2016
09
01
Ultrasound Promoted Efficient Synthesis of some Amides from Nitriles in Ambient Condition
172
176
EN
Reza
Ranjbar-Karimi
Vali-e-Asr University
r.ranjbarkarimi@vru.ac.ir
Fahimeh
Bahadornia
Vali-e-Asr University
karimi_r110@yahoo.com
Alireza
Poorfreidoni
Vali-e-Asr University of Rafsanjan
alireza.poorfreidoni@stu.vru.ac.ir
10.22036/org.chem..2016.15545
Some amide derivatives have been synthesized by the reaction of corresponding nitriles with potassium <em>tert</em>-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.
Ultrasound irradiation,Amide,Nitrile,Synthesis,Room tempereture
https://www.orgchemres.org/article_15545.html
https://www.orgchemres.org/article_15545_e1f41a3b93f98fec63f1f0fe1ee23126.pdf
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2
2
2016
09
01
Magnesium Oxide Nanoparticles for Catalytic Synthesis of 2-Substituted Alcohols from Regioselective Ring Opening of Epoxides in Water
177
191
EN
Mona
Hosseini-Sarvari
Shiraz University
hossaini@shirazu.ac.ir
Golnaz
Parhizgar
10.22036/org.chem..2016.15813
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.
Nano MgO,Ring Opening,Epoxides,1,2-Diols,2-Substituted diols
https://www.orgchemres.org/article_15813.html
https://www.orgchemres.org/article_15813_8f08ee383da7cd4bf98869e0e53b7fbb.pdf
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2
2
2016
09
01
Synthesis and Pesticide Activity of some New Arylic and Pyridylic Oxime Ether Derivatives of Ionone
192
196
EN
Motahareh
Irani
Vali-e-Asr University
m.irani@stu.vru.ac.ir
Reza
Ranjbar-Karimi
Vali-e-Asr University
r.ranjbarkarimi@vru.ac.ir
Hamzeh
Izadi
vali-e-Asr university
izadi@vru.ac.ir
10.22036/org.chem..2016.15814
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 <em>via</em> aromatic nucleophilic substitution (S<sub>N</sub>Ar). The structures of these compounds were elucidated by IR, <sup>1</sup>H NMR, <sup>19</sup>F NMR and <sup>13</sup>C NMR spectroscopic methods. All the compounds were screened <em>in vitro</em> against the common <em>pistachio psylla</em>,<em> Agonoscena pistaciae</em>,<em> fifth instar nymphs</em>. Results showed that compound 3c (LC50 value of 227.76 mg l<sup>-1</sup>) was much more toxic to <em>fifth instar nymphs </em>ofcommon <em>pistachio psylla</em> than compound 3a (LC50 = 1539.14 mg l<sup>-1</sup>) and compound 3f (LC50 = 569.319 mg l<sup>-1</sup>).
Oxime ether,pesticide,Synthesis,Ultrasonic irradiation,Agonoscena pistaciae
https://www.orgchemres.org/article_15814.html
https://www.orgchemres.org/article_15814_a7f584b094a14a2bc1436cc032f4718c.pdf
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2
2
2016
09
01
Design, Characterization and Application of SO3H-Functionalized Phthalimide as a Highly Efficient Catalyst for the Condensation of Dimedone with Arylaldehydes, β-Ketoesters and Ammonium Acetate
197
207
EN
Zahra
Kordrostami
interest
zr.kordrostami@gmail.com
10.22036/org.chem..2016.17602
In this work, SO<sub>3</sub>H-functionalizedphthalimide (SFP) as a SO<sub>3</sub>H-containing solid acid is prepared by the reaction of phthalimide with chlorosulfonic acid, and characterized by FT-IR, <sup>1</sup>H and <sup>13</sup>C 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.
SO3H-functionalized phthalimide (SFP),SO3H-containing solid acid,Dimedone,Arylaldehyde,β-Ketoester,Polyhydroquinoline
https://www.orgchemres.org/article_17602.html
https://www.orgchemres.org/article_17602_f3c5bd23ec787ab62bb43e75157d7326.pdf