eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2020-06-01
6
1
1
12
10.22036/org.chem.2019.159259.1183
89792
Aluminum Oxide Nanoparticle as a Valuable Heterogeneous Nanocatalyst in the Synthesis of 2-Aminothiazole Scaffolds
Zahra Shokrani
shokrani.zahra@yahoo.com
1
Zohre Zarnegar
z_zarnegar@yahoo.com
2
Javad Safari
safari@kashanu.ac.ir
3
aLaboratory of Organic Compound Research, Department of Organic Chemistry, College of Chemistry and Biochemistry, University of Kashan, P.O. Box: 87317-51167, Kashan, I.R, Iran.
Research Affiliate, Department of Chemistry, University of Payame Noor, P.O. BOX 19395-4697, Tehran-IRAN
aLaboratory of Organic Compound Research, Department of Organic Chemistry, College of Chemistry and Biochemistry, University of Kashan, P.O. Box: 87317-51167, Kashan, I.R, Iran.
An efficient methodology for the preparation of 2-aminothiazoles is achieved by one-pot reaction of methylcarbonyls, thiourea and iodine in the presence of an aluminum oxide nanoparticle as an active nanocatalyst at 85 °C in DMSO solvent. Al2O3 nanoparticles have been prepared via co-precipitation method and their structures were confirmed using Fourier transform infrared radiation (FT-TR), X-ray diffraction (XRD), scanning electron microscopic (SEM), and energy-dispersive analysis of X-ray (EDAX) analyses. Advantages of this efficient synthetic approach include higher purity and excellent yield of products, easy isolation of products and convenient manipulation.
https://www.orgchemres.org/article_89792_b7a9343f4809bd8052efb8eebadc4277.pdf
1
3-Thiazoles
Al2O3 nanoparticles
Methylcarbonyls
One-pot synthesis
Heterogeneous catalyst
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2020-06-01
6
1
13
24
10.22036/org.chem.2019.161099.1186
92020
Catalyst-Free One-Pot Four-Component Synthesis of 3-(Imino)-pyrrolo[2,1-a]isoquinolines in Glycerol: Two Different Products through Two Different Purification Methods
Seyed Ali Jehbez
jehbez.ali@yahoo.com
1
Hamidreza Safaei
safaei@iaushiraz.ac.ir
2
Mohsen Shekouhy
m.shekouhy@gmail.com
3
Department of Applied Chemistry, Shiraz Branch, Islamic Azad University, P.O. Box 71993-5, Shiraz, Iran
Department of Applied Chemistry, Shiraz Branch, Islamic Azad University, P.O. Box 71993-5, Shiraz, Iran
Chemistry Department, College of Sciences, Shiraz University, Shiraz, Iran
The one-pot four component synthesis of 3-(Imino)-2,3-dihydropyrrolo[2,1-a]isoquinoline-1,1(10bH)-dicarbonitrile derivatives via a catalyst-free reaction between aryl aldehydes, malononitrile, isoquinoline and isocyanides was successfully conducted in glycerol as a benign, nontoxic and biodegradable promoting reaction medium. The progress of the reaction with two different common purification methods were investigated. Moreover, synthesized products were examined as chemical sensors for the detection of a wide range of metal ions and it was successful for the detection of Co2+ ions.
https://www.orgchemres.org/article_92020_ffef33b0f49ee8800e3529739d346aef.pdf
Multicomponent synthesis
In column chromatography reaction
Glycerol
Sustainable reaction medium
Isocyanide
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2020-06-01
6
1
25
35
10.22036/org.chem.2018.134238.1154
92818
Milled and efficient synthesis and structural study of 4-phenylsulfonyl-2,3,5,6-tetrachloropyridine
Marziyeh Mohammadi
m.mohammadi@vru.ac.ir
1
Reza Ranjbar-Karimi
r.ranjbarkarimi@vru.ac
2
Marjan Ghafari
ghafarimarjan1991@yahoo.com
3
Ali Reza Poorfreidoni
m_mohammadi20002004@yahoo.com
4
Department of Chemistry, Faculty of Science, Vali-e-Asr University of Rafsanjan, Rafsanjan,Iran
Department of Chemistry, Faculty of Science, Vali-e-Asr University of Rafsanjan, Rafsanjan, Iran
Department of Chemistry, Faculty of Science, Vali-e-Asr University of Rafsanjan, Rafsanjan, Iran
Department of Chemistry, Faculty of Science, Vali-e-Asr University of Rafsanjan, Rafsanjan, Iran
4-phenylsulfonyl-2,3,5,6-tetrachloropyridine was synthesized by the reaction of pentafluoropyridine with sodium benzenesulfonate under ultrasonic irradiation. This new methodology provides the excellent yield in a very short reaction time at 0 oC. In the presence of ultrasound irradiation, the yield was 90% after 8 min, by using our previously established method the yield was 85% after 10 h. Also, in this research, the substituent effect in meta and para position of phenyl ring on intramolecular halogen bond strength has been investigated by theoretical studies. The calculations were performed with Gaussian09 software in M05-2X/6-311++G(d,p) level. The results show that one of the oxygen atoms of the SO2 group is co-planer with the pyridine ring and the other oxygen atom is out of this plane. Also, it is observed that the electron-withdrawing groups in meta and para positions reinforced the halogen bond that the oxygen atom of the SO2 group is co-planer with pyridine ring. An opposite behavior is observed for electron-donating groups.
https://www.orgchemres.org/article_92818_a104aa2df41ceeea09ebd2fed5d1f795.pdf
Pentachloropyridine
2
3
5
6-Tetrachloro-4-phenylsulphonylpyridine
Synthesis
Ultrasound irradiation
Halogen bond
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2020-06-01
6
1
36
53
10.22036/org.chem.2019.152131.1173
92819
Interaction of Vitamin B3 with Parent Uracil and Anticancer Uracils: A Detailed Computational Approach
Fatemeh Ravari
fatemeravari@yahoo.com
1
Azadeh Khanmohammadi
az_khanmohammadi@yahoo.com
2
Chemistry Department, Payame Noor University, Tehran 19395-4697, Iran
Chemistry Department, Payame Noor University, Tehran 19395-4697, Iran
A detailed study on the formed complexes from interaction between vitamin B3 with parent uracil and anticancer uracil's is performed using M06-2X/6-311++G(d,p) and B3LYP/6-311++G(d,p) levels of theory. In the studied systems, the uracil's can be placed in three preferential interaction sites (A1–A3) in the vicinity of the vitamin B3. For each uracil group, three configurations corresponding to energetic local minima are obtained. Among the various hydrogen bonding sites, the A1 region of uracil's shows the strongest interactions at both levels of theory. The analyzed dimers are also stabilized by two hydrogen bonds (H-bonds). The predicted H-bonds in the formation of complexes are: O∙∙∙H-N and O(S)∙∙∙H-O. The topological properties of the electron density distribution are also analyzed in terms of the Quantum Theory of “Atoms in Molecules” (QTAIM). Furthermore, the natural bond orbital (NBO) analysis is applied to get a more precise insight about the nature of the H-bond interactions. The calculations reveal that, in most cases, the O(S)∙∙∙H-O H-bonds are stronger than the O∙∙∙H-N ones. The calculated energies of highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) show that charge transfer occurs within the molecules.
https://www.orgchemres.org/article_92819_b5085344574d55609a8ffe746b3d64a4.pdf
Vitamin B3
Anticancer uracils
DFT
NBO
QTAIM
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2020-06-01
6
1
54
68
10.22036/org.chem.2019.158492.1181
93729
MnFe2O4 MNPs Anchored Chitosan-Bu-SO3H as a Recyclable Nanocatalyst for Sonochemical One Pot Heterocyclization of Indandione with Aniline and Acenaphthoquinone in Aqueous Media
Hossein Naeimi
naeimi@kashanu.ac.ir
1
Sepideh Lahouti
2
Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Iran
Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, 87317, I.R. Iran
In this research, the successful synthesis of spiro[acenaphthylene-1,9'-acridine] triones using 1,3-indandione, aniline and acenaphthoquinone in the presence of magnetic MnFe2O4@CS-Bu-SO3H NPs catalyst under ultrasonic irradiation in water is described. The catalyst was fully characterized by scanning electronic microscopy (SEM), vibrating sample magnetometer (VSM), X-ray diffraction (XRD), thermal gravimetric analysis (TGA), energy dispersive X-ray (EDX) and furrier transfer- infrared (FT-IR) spectroscopy. This method offers several advantages such as easy work-up, excellent yields, short reaction times, using of ultrasonic method, recoverability of the catalyst and little catalyst loading.
https://www.orgchemres.org/article_93729_e5f32b0f7af84c9a51df20b085436afb.pdf
Ultrasound
Spiroheterocycles
Magnetic nanoparticles
MnFe2O4@CS-Bu-SO3H
Chitosan
Five-component
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2020-06-01
6
1
69
81
10.22036/org.chem.2019.175928.1195
93731
Synthesis of 2,4,5-Tri substituted Imidazoles Using Nano-[Zn-2BSMP]Cl2 as a Schiff Base Complex and Catalyst
hamid Goudarziafshar
hamid_gafshar@yahoo.com
1
Ahmad Reza Moosavi-Zare
moosavizare@yahoo.com
2
Zahra Jalilian
jaliliyan.zahra96@gmail.com
3
Sayyed Jamaleddin Asadabadi University, Asadabad, 6541835583, I. R. Iran
Department of Chemistry, University of Sayyed Jamaleddin Asadabadi, Asadabad 6541835583, Iran
Sayyed Jamaleddin Asadabadi University, Asadabad, 6541861841, I. R. Iran
Nano-Zn-[2-boromophenyl-salicylaldimine-methylpyranopyrazole]Cl2 nanoparticles (nano-[Zn-2BSMP]Cl2) as a Schiff base complex and catalyst was used for the preparation of 2,4,5-tri substituted imidazoles by the one-pot multi-component condensation reaction of benzil with various aromatic aldehydes and ammonium acetate at 80 °C under solvent-free conditions.
https://www.orgchemres.org/article_93731_171e514346e3b470964ccde9887f5b57.pdf
Multi-component reaction
Nano-[Zn-2BSMP]Cl2
Schiff base complex
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2020-06-01
6
1
82
91
10.22036/org.chem.2019.150835.1170
96485
Green and Convenient Synthesis of Polyfunctionalized Piperidines Catalyzed by Ascorbic Acid under Ambient Temperature
Farzaneh Mohamadpour
mohamadpour.f.7@gmail.com
1
Mojtaba Lashkari
m.lashkari@velayat.ac.ir
2
Nourallah Hazeri
nhazeri@chem.usb.ac.ir
3
Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran
Faculty of Science, Velayat University, Iranshahr, Iran
Department of Chemistry, Faculty of Sciences, University of Sistan and Baluchestan, Zahedan 98135-674, Iran
A green and mild synthetic route to the convenient preparation of polyfunctionalized piperidines have been developed using ascorbic acid as a green and biodegradable catalyst via Knoevenagel- intramolecular [4+2] aza-Diels-Alder imin-based reaction in ethanol media. All reactions are completed by a five-component condensation reaction between 1,3-dicarbonyl compounds, aromatic aldehydes and various amines in short period of times and the products are obtained in good to high yields. The salient features of this environmentally friendly approach are green, biodegradable and readily available catalyst, straightforward work-up with no column chromatographic separation, mild reaction conditions, high atom-economy, avoidance of toxic organic solvents and highly efficient.
https://www.orgchemres.org/article_96485_da520bd42a495a75db32863e4da8989c.pdf
Ascorbic acid
Polyfunctionalized piperidines
Green procedure
Ethanol media
Simple work-up
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2020-06-01
6
1
92
99
10.22036/org.chem.2019.191065.1208
99595
Bis (1(3-trimethoxysilylpropyl)-3-methyl-imidazolium) Nickel Tetrachloride Tethered to Colloidal Silica Nanoparticles as a Superior Catalyst for the Bis-thiazolidinones Preparation
Javad Safaei-Ghomi
safaei@kashanu.ac.ir
1
Seyed Hadi Nazemzadeh
shnazem@gmail.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
An easy and rapid method for the synthesis of bis-thiazolidinones has been presented by one-pot pseudo-five-component reaction of benzaldehydes, ethylenediamine, 2-mercaptoacetic acid with bis (1(3-trimethoxysilylpropyl)-3-methyl-imidazolium) nickel tetrachloride tethered to colloidal silica nanoparticles. Atom economy, low catalyst loading, reusable catalyst, applicability to a wide range of substrates and high yields of products are some of the important features of this protocol.
https://www.orgchemres.org/article_99595_c9dbf40c5ddba8a8a645446941941bbe.pdf
Heterogeneous catalysts
Ionic Liquid
Colloidal silica
Bis-thiazolidinones
One-pot
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2020-06-01
6
1
100
120
10.22036/org.chem.2019.189754.1207
105879
Two Independent Intermolecular 1D-Polymeric H-Bonds between Each Enantiomer in Octahydro-1H-Xanthene-1,8(2H)-Diones and Bis-Xanthen Analogues: Synthesis and Crystal Structure
Nader Noroozi Pesyan
n.noroozi@urmia.ac.ir
1
F. Karimi
2
H. Batmani
3
T. Tunç
4
E. Şahin
5
Department of Organic Chemistry, Faculty of Chemistry, Urmia University, 57159, Urmia, Iran
Department of Organic Chemistry, Faculty of Chemistry, Urmia University, 57159, Urmia, Iran
Department of Organic Chemistry, Faculty of Chemistry, Urmia University, 57159, Urmia, Iran
Department of Science Education, Faculty of Education, Aksaray University, TR-68100, Aksaray, Turkey
Department of Chemistry, Faculty of Science, Atatürk University, TR-25240 Erzurum, Turkey
Reaction of 1,3-cyclohexanedione, aldehydes, and cyanogen bromide leads to the selective formation of octahydro-1H-xanthene-1,8(2H)-diones in moderate to good yields at room temperature under basic condition. The reaction of dialdehydes such as phthalaldehyde and terphthalaldehyde gaves tetrahydrodibenzo[b,e]oxepin-1(2H)-one and bifunctiolalized linked bis-xanthen analogues, respectively. All structures were characterized by FT IR, 1H and 13C NMR spectroscopy and Mass analysis techniques. The structure of 3c was analyzed by X-ray crystallography. The pKa and hydrogen bond strength (EHB) were determined in results of ≈11.7 and to ≈5 kcal.mol-1, respectively, via d(O•••••O) distance.
https://www.orgchemres.org/article_105879_cbe49e4a7f86f1983331512f739c8929.pdf
1
3-cyclohexanedione
Octahydro-1H-xanthene-1
8(2H)-dione
One-pot
Xanthene
Polymeric H-bond
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2020-06-01
6
1
121
130
10.22036/org.chem.2020.184080.1199
105880
3-Methyl-1-sulfonic Acid Imidazolium Mesylate as a Novel, Highly Effective and Dual-functional Catalyst for the Solvent-free Production of Bis-coumarins
Aseih Kargar-Dolatabadi
2920kargarda@gmail.com
1
Seyed Sajad Sajadikhah
sssajadi@pnu.ac.ir
2
Abdolkarim Zare
abdolkarimzare@yahoo.com
3
Alemeh Razaghi
arazzaghi1@yahoo.com
4
Department of Chemistry, Payame Noor University, P. O. Box 19395-3697, Tehran, Iran.
Department of Chemistry, Payame Noor University, P. O. Box 19395-3697, Tehran, Iran
Department of Chemistry, Payame Noor University, PO BOX 19395-3697, Tehran, Iran
Department of Chemistry, Payame Noor University, PO BOX 19395-3697, Tehran, Iran
A novel ionic liquid entitled 3-methyl-1-sulfonic acid imidazolium mesylate ([Msim][OMs]) was synthesized, and characterized by studying its FT-IR, 1H NMR, 13C NMR and mass spectra. This ionic liquid was employed as a dual-functional catalyst for the preparation of bis-coumarins via the one-pot pseudo three-component reaction of 4-hydroxycoumarin (2 eq.) and arylaldehydes (1 eq.) under solvent-free and relatively mild conditions. Owing to dual-functionality of [Msim][OMs] (having acidic and basic sites), it could act as a highly effective catalyst for the reaction. Additionally, an attractive mechanism based on dual-functionality of the catalyst was proposed.
https://www.orgchemres.org/article_105880_c61508e56b5d73348d1b9fef8aa0b9ab.pdf
Ionic Liquid
3-Methyl-1-sulfonic acid imidazolium mesylate ([Msim][OMs])
Bis-coumarins
Dual-functional catalyst
Solvent-free
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2020-06-01
6
1
131
136
10.22036/org.chem.2020.184426.1200
107410
Aldoses and Ketoses’ Extended Binary and Decimal Numbers: A Logical and Simple Relationship between Name and Structure
Ahmad Khorramabadi-zad
khoram@gmail.com
1
Azam Shiri
amshiri@gmail.com
2
Faculty of Chemistry, Bu-Ali Sina University, Hamedan 6517838695, Iran
Department of Applied Chemistry, Malayer University, Malayer 65719-95863, Iran
Herein, we propose a very simple and useful method for naming aldoses and ketoses (Fischer projection and cyclic structures) and drawing their structures from their names with the aid of binary and decimal numbers. Fischer projections can be converted simply to the corresponding cyclic and Haworth forms and vice versa. Also one can easily find the R or S descriptors of any chiral center with the aid of a given binary number, without going through with the priority of its attached groups and, draw the enantiomer of any given monosaccharide.
https://www.orgchemres.org/article_107410_cf9178d42b6bc52cf531a2628d5a4c1b.pdf
Aldose
Ketose
Binary number
Decimal number
Fischer form
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2020-06-01
6
1
137
149
10.22036/org.chem.2020.202084.1217
107411
Friedländer Synthesis of Substituted Quinolines Using an Efficient and Reusable Brønsted Acid Ionic Liquid Supported on Fe3O4@SiO2 Nanoparticles under Solvent-free Conditions
Mehdi Fallah-Mehrjardi
fallah.mehrjerdi@pnu.ac.ir
1
Samaneh Kalantari
s.kalantari68@gmail.com
2
Department of Chemistry, Payame Noor University, Tehran, 19395-4697, Iran
Department of Chemistry, Payame Noor University (PNU), P.O. Box 19395-3697, Tehran, Iran
In this study, a highly efficient and recyclable Brønsted acid ionic liquid, 1-methyl-3-(3-triethoxysilylpropyl)-1H-imidazol-3-ium hydrogensulfate, immobilized on the surface of Fe3O4@SiO2 (MNP-IL-HSO4) was prepared and characterized. Then, the catalytic activity of this nanomagnetic catalyst was investigated in the Friedländer synthesis of substituted quinolines through the cyclocondensation reaction of o-aminoaryl ketones with α-methylene carbonyl compounds under solvent-free conditions. The present protocol has several advantages, including short reaction times, high yield of products, simplicity in operation, simple work-up and reusability of the catalyst.
https://www.orgchemres.org/article_107411_8efdbefbe554da26f5be22e50732e375.pdf
Magnetic nanoparticles
Supported ionic liquids
Quinolines
Friedländer synthesis
Solvent-free conditions