eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2020-05-01
6
2
150
158
10.22036/org.chem.2020.203724.1218
107626
Heterogeneous Copper Nanoparticle on Charcoal (Cu/C) Mediated Efficient Synthesis of 1-Substituted 1H-Tetrazoles under Solvent Free Condition
Reza Khalifeh
khalifeh@sutech.ac.ir
1
Monire Noori
noori.monire@ymail.com
2
Department of Chemistry, Shiraz University of Technology, Shiraz 71555-313
Department of Chemistry, Shiraz University of Technology, Shiraz , Iran
1-substituted 1H-tetrazoles were efficiently synthesized under solvent-free conditions from the reaction of primary amines, triethylorthoformate, and sodium azide in the presence of Cu/C as a heterogeneous catalyst. Various amines including aromatic and heteroaromatic amines were used to afford the corresponding products in good to excellent yields. The characterization of corresponding products were also performed applying several analysis techniques such as infrared spectroscopy, 1H-NMR, 13C-NMR and elemental analyses. The catalyst can be recycled and reused for five times without noticeable loss of its activity. This procedure has various benefits include high yields, low cost, fast reaction and reusability of the catalyst.
https://www.orgchemres.org/article_107626_829df3e72c1938610eddbd7d396f3dda.pdf
Tetrazole derivatives
Cu/C
Heterogeneous catalyst
Multicomponent reaction
Solvent-free conditions
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2020-05-01
6
2
159
172
10.22036/org.chem.2020.217095.1230
107627
Sulfanilic Acid Supported on Magnetic Nanoparticles as a Green Catalyst for the Sonosynthesis of 1,4-Diazepines Containing Tetrazole Ring
Javad Safaei-Ghomi
safaei@kashanu.ac.ir
1
Soleiman Paymard-Samani
spsamani84@yahoo.com
2
Hossein Shahbazi-Alavi
hossien_shahbazi@yahoo.com
3
Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, P.O. Box 87317-51167, I. R. Iran
Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, P.O. Box 87317-51167, I. R. Iran
Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, P.O. Box 87317-51167, I. R. Iran
Magnetic nanoparticle-supported sulfanilic acid (MNPs-PhSO3H) has been used as an efficient catalyst for the preparation of 1,4-diazepines containing tetrazole ring. The catalyst has been characterized by FT-IR (Fourier-transform infrared spectroscopy), SEM (scanning electron microscope), XRD (X-ray diffraction) and VSM (vibrating-sample magnetometer). The present synthetic protocol provides several advantages such as easy work-up, excellent yields, short reaction times, reusability of the catalyst and low catalyst loading. The present catalytic procedure is extensible to a wide diversity of substrates for the synthesis of a variety-oriented library of 1,4-diazepines containing tetrazole ring.
https://www.orgchemres.org/article_107627_e8c43687eb928166085bc2fc1ee99431.pdf
1
4-Diazepine
Magnetic nanoparticles
Ultrasonic irradiation
Heterogeneous catalyst
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2020-05-01
6
2
173
178
10.22036/org.chem.2020.214359.1227
109428
Synthesis of Functionalized Dihydropyrimidothiazinoquinoline Derivatives via Reaction of 3-(Chloromethyl)-2-chloroquinolines and 2-Thioxo-2,3-dihydropyrimidin-4(1H)-one
Morteza Shiri
mshiri@alzahra.ac.ir
1
Shima Fazelzadeh
2
Vahideh Zadsirjan
3
Chemistry Department, Faculty of Physics and Chemistry, Alzahra University, Vanak, 1993893973 Tehran, Iran
Chemistry Department, Faculty of Physics and Chemistry, Alzahra University, Vanak, 1993893973 Tehran, Iran
Chemistry Department, Faculty of Physics and Chemistry, Alzahra University, Vanak, 1993893973 Tehran, Iran
An efficient method for the synthesis of novel dihydropyrimidothiazinoquinoline derivatives through the reaction of 2-chloro-3-(chloromethyl)quinolines and 2-thioxo-2,3-dihydropyrimidin-4(1H)-one in the presence of K2CO3 is demonstrated.
https://www.orgchemres.org/article_109428_0660b6b04d1139063ba6c331012bd995.pdf
quinoline
Cyclization
3-(Chloromethyl)-2-chloroquinolines
Cascade reaction
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2020-05-01
6
2
179
187
10.22036/org.chem.2020.189549.1206
109429
Application of Chlorophyll Extracted from Spinach as a Green and affordable Catalyst for the Synthesis of Tetrahydrobenzo[b]pyran and Pyrano[c]chromene
Moheb Shirzaei
m.shirzaei@yahoo.com
1
Ebrahim Mollashahi
mollashahi39@chem.usb.ac.ir
2
Malek Taher Maghsoodlou
mt_maghsoodlou@yahoo.com
3
Mojtaba Lashkari
mojtaba_chem_84@yahoo.com
4
Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box98135-674, Zahedan, Iran
Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran
Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box98135-674, Zahedan, Iran
Faculty of Sciences, Velayat University, Iranshahr, Iran
Chlorophyll is a natural pigment used for the synthesis of organic substances for instance sugars. At mild conditions, chlorophyll was employed as a green catalyst for the synthesis of tetrahydrobenzo[b]pyran and 3,4-dihydropyrano[c]chromene from the condensation between aromatic aldehydes, malononitrile, and 4-hydroxy-2H-chromen-2-one is an active enolic compound. This methodology has a considerable number of advantages such as mild conditions, natural, affordable catalyst, excellent yields, eco-friendly and, short reaction time. Another point worth mentioning is that purification of the products does not require sophisticated methods like column chromatography.
https://www.orgchemres.org/article_109429_546b2474dfb7f7c196707b31065caf98.pdf
Chlorophyll
Natural catalyst
Tetrahydrobenzo[b]pyran
3
4-Dihydropyrano[c]chromene
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2020-05-01
6
2
188
201
10.22036/org.chem.2020.223422.1237
114188
Synthesis, Structural Characterization and EF-QTAIM Study of a New Schiff Base Ligand, Pyridine 3-Carbaldehyde Thiosemicarbazone (as a Molecular Wire)
Reza Safari
safari_physicalchemistry@yahoo.com
1
Younes Hanifehpour*
younes.hanifehpour@gmail.com
2
babak Mirtamizdousta
babakm.tamizdoust@gmail.com
3
Ebrahim Honarmanda
e.honarmand@qom.ac.ir
4
Department of Chemistry, Faculty of Science, University of Qom, PO Box 37185-359, Qom, Iran
Faculty of Science, Department of Chemistry, SayyedJamaleddinAsadabadi University, Asadabad, Iran
Department of Chemistry, Faculty of Science, University of Qom, PO Box 37185-359, Qom, Iran
Department of Chemistry, Faculty of Science, University of Qom, PO Box 37185-359, Qom, Iran
A new Schiff base ligand, pyridine 3-carbaldehye thiosemicarbazone (1), was synthesized and structurally characterized. Its synthesis involves a Schiffbase condensation of thiosemicarbazide and pyridine 3-carbaldehyde. The new compound was determined through elemental analyses, FT-IR spectroscopy, and single-crystal X-ray crystallography. Compound 1 has a monoclinic crystallographic system with a P21/n space group. It can be introduced as a tridentate NNS donor ligand for the synthesis of several complexes with new structures. With several H-bonding, the structure showed the three-dimensional structures.Inaddition, the electronic properties of pyridine 3-carbaldehyde thiosemicarbazone are studied, in atomic-scale,using density functional theory (DFT) at and quantum theory of atoms in molecules (QTAIM). Also, the external electric field (EF) effects on electronic/vibrationalpropertiescharacteristics of this molecular system (as molecular wire) are studied, using QTAIM, at theatomic scale (EF-QTAIM).Moreover, analysis of the current-voltage (I-V) curve results showed that this molecule can be used as a stable molecular wire.
https://www.orgchemres.org/article_114188_48ce2d925ae25eb10cb77914a70ac952.pdf
crystal structure
Schiff base ligand
Thiosemicarbazone
H-bonding
QTAIM
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2020-05-01
6
2
202
211
10.22036/org.chem.2020.226164.1240
114256
Nano-sawdust/Sn(IV) as an Efficient Bio-based Nano-catalyst for the Synthesis of Highly Substituted Dihydro-2-oxopyrroles
Bi Bi Fatemeh Mirjalili
fmirjalili@yazd.ac.ir
1
Fateme Hakimi Saryazdi
fatemeh.hakimi@yahoo.com
2
Department of Chemistry, College of Science, Yazd University, Yazd, P. O. Box: 89195-741,I. R. Iran
Department of chemistry, Faculty of science, Payame noor University, Tehran, Iran
Nano-sawdust/Sn(IV) was used as a readily available, inexpensive, biodegradable and environmentally benign heterogeneous solid acid biocatalyst for the one pot cascade synthesis of highly functionalized dihydro-2-oxypyrroles. Four-component reactions (4CRs) of the dialkylacetylenedicarboxylates, amines and aldehydes were used for the synthesis of highly functionalized dihydro-2-oxypyrroles under thermal conditions.
https://www.orgchemres.org/article_114256_16c0d7ec63572840e5991a31c6f23471.pdf
Nano-sawdust/Sn(IV)
Dihydro-2-oxopyrrole
Multicomponent reaction
Solid acid nano-atalyst
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2020-05-01
6
2
212
218
10.22036/org.chem.2020.222226.1234
114257
Efficient synthesis of N-amino pyridine-2,6-diones via a novel one-pot, the three-component reaction between 2-cyanoacetohydrazide, Meldrum's acid, and aryl aldehyde
Sara Asadi
saraasadi67@yahoo.com
1
Farzaneh Alizadeh-Bami
f.alizadeh.bami@gmail.com
2
Hossein Mehrabi
mehraby_h@yahoo.com
3
Department of Chemistry, Vali-e-Asr University of Rafsanjan, 77176 Rafsanjan, Iran
Department of Chemistry, Vali-e-Asr University of Rafsanjan, 77176 Rafsanjan, Iran
Department of Chemistry, Vali-e-Asr University of Rafsanjan, 77176, Rafsanjan, Iran.
A new and efficient approach has been developed for the synthesis of N-amino pyridine-2,6-dione derivatives by a one-pot, three-component reaction of 2-cyanoacetohydrazide, Meldrum's acid, and aryl aldehyde in the presence of piperidine in DMF. All the products were obtained in excellent yields and their structures were established from their spectroscopic data.
https://www.orgchemres.org/article_114257_a52e5dce5b877fed33cc04da315ae525.pdf
2-Cyanoacetohydrazide
Meldrum's acid
Aryl aldehyde
N-Amino pyridine-2
6-dione
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2020-05-01
6
2
219
232
10.22036/org.chem.2019.204444.1220
116579
ZnO@zeolite-Y Mesoporous as an Eco-friendly and Efficient Nanocatalyst in the Three-component Synthesis of 2-Amino-benzochromenes
Mehdi Kalhor
mekalhor@gmail.com
1
Mansour Bigdeli
che.bigdeli@yahoo.com
2
S. Ahmad Mirshokraie
a.mirshokraie@gmail.com
3
Hassan Moghanian
moghanian@gmail.com
4
Department of Chemistry, Payame Noor University, 19395-4697, Tehran, Iran
Department of Chemistry, Payame Noor University, 19395-4697, Tehran, Iran
Department of Chemistry, Payame Noor University, 19395-4697, Tehran, Iran
Department of Chemistry, Dezful Branch, Islamic Azad University, Dezful, Iran
A streamlined and efficient method for the synthesis of 2-amino-4H-chromenes is achieved by one-pot three-component reaction of aldehydes, 2-naphthol and malononitrile in the presence of ZnO nanoparticles loaded on zeolite-Y (ZnO@zeolite-Y) as a highly active catalyst under solvent-free conditions. ZnO@zeolite-Y has been successfully prepared via hydrothermal technique and its structure was confirmed using nanoscale-like identification techniques included FT-IR, XRD, FE-SEM, EDX analyses and BET surface area measurements. The higher environmental compatibility and sustainability factors such as reusability of the catalyst as an important principle in green chemistry, use of solvent-less technique as a green synthetic approach and easy isolation of the product along with good yields, make the present protocol a true green process for the synthesis of chromenes compared to conventional methods.
https://www.orgchemres.org/article_116579_45896aecdd980da6f1768f2e085282d6.pdf
ZnO nanoparticles
Zeolite-Y
nanocatalyst
Multi-component synthesis
2-Amino-4H-benzochromene
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2020-05-01
6
2
233
241
10.22036/org.chem.2020.234855.1246
119459
Ionic Liquid Based Polyoxometalate as an Industrial Candidate for Extractive Desulfurization without Chemical Intermediates Production
Fakhrosadat Mirnezami
fs_mirnezami@yahoo.com
1
Ezzat Rafiee
ezzat_rafiee@yahoo.com
2
Faculty of Chemistry, Razi University, Kermanshah, 6714414971, Iran
Faculty of Chemistry, Razi University, Kermanshah, 6714414971, Iran. Institute of Nano Science and Nano Technology, Razi University, Kermanshah, 6714414971, Iran
Abstract This work involves the extractive oxidation of mixed thiophenic compounds model oil over an oxidative polyoxometalate-based catalytic system. Phosphotungstic acid-pyridine compound combining of Keggin-structured polyoxometalate anion with sulfonate functionalized cation was applied as catalyst in sulfur removal. Model oil was simulated using a mixture of the sulfur compounds dibenzothiophene, benzothiophene and thiophene in n-heptane. At optimization strategy, different extractive solvents including isopropanol, ethanol, dimethylformamid and acetonitrile in desulfurization performance were used. Some important reaction parameters including catalyst loading, dose of the oxidizing agent, existence of nitrogen compounds and aromatic hydrocarbons (toluene, xylene and mesitylene) were considered on the oxidative desulfurization (ODS) via a one-step process under optimized conditions.
https://www.orgchemres.org/article_119459_cf6f5c6ab98c69bd9fa6a8e6fd028f33.pdf
Model oil
Desulfurization
Extraction
Ionic Liquids
Polyoxometalate
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2020-05-01
6
2
242
256
10.22036/org.chem.2020.228472.1242
125418
Theoretical Study on the Interaction between 5-Fluorouracil Anticancer Drug and Nitrosamine as a Family of Potent Carcinogenic Compounds in Different Solvents: A Quantum Chemical Study
Leila Hokmabadi
lhokmabady8223@gmail.com
1
Azadeh Khanmohammadi
az_khanmohammadi@yahoo.com
2
Department of Chemistry, Payame Noor University, Tehran 19395-4697, Iran
Young Researchers and Elite Club, Quchan Branch, Islamic Azad University, Quchan, Iran
In this research, the effect of different solvents on the stability order, binding energy and hydrogen bond (H-bond) strength of Fluorouracil-Nitrosamine (FU–NA) complex is investigated by using the density functional theory (DFT). The calculations are conducted on M06-2X/6-311++G(d,p) level of theory for optimization of complex geometries and their monomers. Based on the average of the calculated H-bond energies, the H-bond strength in the gas phase is higher than the solution phase and in the polar solvents are close to each other and lower than the non-polar ones. Our findings also show that when the solvent effect is applied the binding energy of complex is significantly changed. The binding energy in the solution phase is also lower than the gas phase. Therefore, the stability in the polar solvents with respect to the water as natural solvent is higher than the non-polar ones. The natural bond orbital (NBO) analysis and the Bader’s quantum theory of “Atoms in Molecules” (QTAIM) are also applied to evaluate the H-bond interactions in the selected solvents.
https://www.orgchemres.org/article_125418_4ffed03057546bdc8db8c00673036168.pdf
5-fluorouracil
Nitrosamine
Solvent effect
NBO
QTAIM
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2020-05-01
6
2
257
271
10.22036/org.chem.2020.231726.1245
125419
Fe2O3@MCM-BP Hybrid Nanocomposite as an Alkaline Magnetic Catalyst in the One-pot Preparation of Various Derivatives of Pyrano [2,3-C] Pyrazole under Solvent-free Conditions
Manoochehr Aghajeri
aghajeri4755@gmail.com
1
Alireza Kiasat
akiasat@scu.ac.ir
2
Haleh Sanaeishoar
halehsanaei@yahoo.com
3
Department of Chemistry, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran. Department of Chemistry, Khuzestan Science and Research Branch, Islamic Azad University, Ahvaz, Iran
Department of Chemistry, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran. Department of Chemistry, College of Science, Shahid Chamran University of Ahvaz, Ahvaz, Iran
Department of Chemistry, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran
In this paper, bi-pyridinium chloride supported on the core-shell mesoporous substrate, Fe2O3@MCM was prepared as an organic-inorganic magnet nanocomposite. Characterization of prepared hybrid nanocomposite, Fe2O3@MCM-BP, has taken using FT-IR spectroscopy, X-ray diffraction (XRD),Scanning electron microscopy (SEM), Transmission electron microscopy (TEM), Thermal gravimetric analysis (TGA), and Vibrational sample magnetometry (VSM) techniques. The efficacy of the nanocomposite as an alkaline heterogeneous magnetic catalyst in the one-pot multicomponent condensation reaction for preparation of various derivatives of pyrano [C-2,3] pyrazole under solvent-free conditions was investigated. High efficiency, ease of manufacture and reusability are some the features of this catalyst.
https://www.orgchemres.org/article_125419_4c9576763914b33f110fd11b8d73dd3e.pdf
Organic-inorganic nano-magnetic composite
MCM-41
Fe2O3@MCM-BP
Pyrano [C-2
3] pyrazole
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2020-05-01
6
2
272
285
10.22036/org.chem.2020.243568.1252
128279
MNPs-TBAN as a Novel Basic Nanostructure and Efficient Promoter for the Synthesis of Pyranopyrimidinones
Elham Khalili
mbodaghi2007@gmail.com
1
Najmieh Ahadi
mojgan_2012@ymail.com
2
Mohammad Ali Bodaghifard
mbodaghi2007@yahoo.com
3
Department of Chemistry, Faculty of Science, Arak University, Arak 38156-88138, Iran
Institute of Nanosciences & Nanotechnology, Arak University, Arak, Iran.
Department of Chemistry, Faculty of science, Arak University, Arak 38156-8-8349, Iran
In this study, magnetite nanoparticles (Fe3O4) were synthesized as a magnetic core by chemical co-precipitation process and coated with a silica layer. The (Fe3O4@SiO2) core-shell magnetic nanoparticles were functionalized by organic-base tags to produce the MNPs-TBAN nanoparticles as a novel hybrid nanostructure. The morphology, stability, and magnetism of this hybrid nanostructure were characterized and studied by Fourier transform infrared spectroscopy (FT-IR), thermal gravimetric analysis (TGA), vibrating sample magnetometry (VSM), X-ray powder diffraction analysis (XRD), scanning electron microscopy (FE-SEM), and transmission electron microscopy (TEM). The prepared hybrid nanomaterial was successfully used as a basic heterogeneous catalyst for the synthesis of pyrano[2,3-d]pyrimidine derivatives, via the condensation of an aldehyde, malononitrile and barbituric acid or thiobarbituric acid. The reaction was afforded the desired products in high purity and has advantages of excellent yields, simple workup procedure, and short reaction time. The catalyst was easily separated from the reaction mixture with the assistance of an external magnet and reused for several runs without noticeable deterioration in catalytic activity.
https://www.orgchemres.org/article_128279_94eadc1b12b926df3d55436a2fc298d2.pdf
Hybrid nanomaterial
Magnetite
Heterogeneous catalysis
Multicomponent reaction
Pyrano[2
3-d]pyrimidine