Iranian Chemical Society
Organic Chemistry Research
2383-242X
6
1
2020
06
01
Aluminum Oxide Nanoparticle as a Valuable Heterogeneous Nanocatalyst in the Synthesis of 2-Aminothiazole Scaffolds
1
12
EN
Zahra
Shokrani
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.
shokrani.zahra@yahoo.com
Zohre
Zarnegar
Research Affiliate, Department of Chemistry, University of Payame Noor, P.O. BOX 19395-4697, Tehran-IRAN
z_zarnegar@yahoo.com
Javad
Safari
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.
safari@kashanu.ac.ir
10.22036/org.chem.2019.159259.1183
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.
1,3-Thiazoles,Al2O3 nanoparticles,Methylcarbonyls,One-pot synthesis,Heterogeneous catalyst
https://www.orgchemres.org/article_89792.html
https://www.orgchemres.org/article_89792_b7a9343f4809bd8052efb8eebadc4277.pdf
Iranian Chemical Society
Organic Chemistry Research
2383-242X
6
1
2020
06
01
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
13
24
EN
Seyed Ali
Jehbez
Department of Applied Chemistry, Shiraz Branch, Islamic Azad University, P.O. Box 71993-5, Shiraz, Iran
jehbez.ali@yahoo.com
Hamidreza
Safaei
0000-0003-0105-162X
Department of Applied Chemistry, Shiraz Branch, Islamic Azad University, P.O. Box 71993-5, Shiraz, Iran
safaei@iaushiraz.ac.ir
Mohsen
Shekouhy
0000-0001-7644-0625
Chemistry Department, College of Sciences, Shiraz University, Shiraz, Iran
m.shekouhy@gmail.com
10.22036/org.chem.2019.161099.1186
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.
Multicomponent synthesis,In column chromatography reaction,Glycerol,Sustainable reaction medium,Isocyanide
https://www.orgchemres.org/article_92020.html
https://www.orgchemres.org/article_92020_ffef33b0f49ee8800e3529739d346aef.pdf
Iranian Chemical Society
Organic Chemistry Research
2383-242X
6
1
2020
06
01
Milled and efficient synthesis and structural study of 4-phenylsulfonyl-2,3,5,6-tetrachloropyridine
25
35
EN
Marziyeh
Mohammadi
Department of Chemistry, Faculty of Science, Vali-e-Asr University of Rafsanjan, Rafsanjan,Iran
m.mohammadi@vru.ac.ir
Reza
Ranjbar-Karimi
Department of Chemistry, Faculty of Science, Vali-e-Asr University of Rafsanjan, Rafsanjan, Iran
r.ranjbarkarimi@vru.ac
Marjan
Ghafari
Department of Chemistry, Faculty of Science, Vali-e-Asr University of Rafsanjan, Rafsanjan, Iran
ghafarimarjan1991@yahoo.com
Ali Reza
Poorfreidoni
Department of Chemistry, Faculty of Science, Vali-e-Asr University of Rafsanjan, Rafsanjan, Iran
m_mohammadi20002004@yahoo.com
10.22036/org.chem.2018.134238.1154
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.
Pentachloropyridine,2,3,5,6-Tetrachloro-4-phenylsulphonylpyridine,Synthesis,Ultrasound irradiation,Halogen bond
https://www.orgchemres.org/article_92818.html
https://www.orgchemres.org/article_92818_a104aa2df41ceeea09ebd2fed5d1f795.pdf
Iranian Chemical Society
Organic Chemistry Research
2383-242X
6
1
2020
06
01
Interaction of Vitamin B3 with Parent Uracil and Anticancer Uracils: A Detailed Computational Approach
36
53
EN
Fatemeh
Ravari
Chemistry Department, Payame Noor University, Tehran 19395-4697, Iran
fatemeravari@yahoo.com
Azadeh
Khanmohammadi
Chemistry Department, Payame Noor University, Tehran 19395-4697, Iran
az_khanmohammadi@yahoo.com
10.22036/org.chem.2019.152131.1173
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.
Vitamin B3,Anticancer uracils,DFT,NBO,QTAIM
https://www.orgchemres.org/article_92819.html
https://www.orgchemres.org/article_92819_b5085344574d55609a8ffe746b3d64a4.pdf
Iranian Chemical Society
Organic Chemistry Research
2383-242X
6
1
2020
06
01
MnFe2O4 MNPs Anchored Chitosan-Bu-SO3H as a Recyclable Nanocatalyst for Sonochemical One Pot Heterocyclization of Indandione with Aniline and Acenaphthoquinone in Aqueous Media
54
68
EN
Hossein
Naeimi
Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Iran
naeimi@kashanu.ac.ir
Sepideh
Lahouti
Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, 87317, I.R. Iran
10.22036/org.chem.2019.158492.1181
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.
Ultrasound,Spiroheterocycles,Magnetic nanoparticles,MnFe2O4@CS-Bu-SO3H,Chitosan,Five-component
https://www.orgchemres.org/article_93729.html
https://www.orgchemres.org/article_93729_e5f32b0f7af84c9a51df20b085436afb.pdf
Iranian Chemical Society
Organic Chemistry Research
2383-242X
6
1
2020
06
01
Synthesis of 2,4,5-Tri substituted Imidazoles Using Nano-[Zn-2BSMP]Cl2 as a Schiff Base Complex and Catalyst
69
81
EN
hamid
Goudarziafshar
Sayyed Jamaleddin Asadabadi University, Asadabad, 6541835583, I. R. Iran
hamid_gafshar@yahoo.com
Ahmad Reza
Moosavi-Zare
Department of Chemistry, University of Sayyed Jamaleddin Asadabadi, Asadabad 6541835583, Iran
moosavizare@yahoo.com
Zahra
Jalilian
Sayyed Jamaleddin Asadabadi University, Asadabad, 6541861841, I. R. Iran
jaliliyan.zahra96@gmail.com
10.22036/org.chem.2019.175928.1195
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.
Multi-component reaction,Nano-[Zn-2BSMP]Cl2,Schiff base complex
https://www.orgchemres.org/article_93731.html
https://www.orgchemres.org/article_93731_171e514346e3b470964ccde9887f5b57.pdf
Iranian Chemical Society
Organic Chemistry Research
2383-242X
6
1
2020
06
01
Green and Convenient Synthesis of Polyfunctionalized Piperidines Catalyzed by Ascorbic Acid under Ambient Temperature
82
91
EN
Farzaneh
Mohamadpour
Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran
mohamadpour.f.7@gmail.com
Mojtaba
Lashkari
Faculty of Science, Velayat University, Iranshahr, Iran
m.lashkari@velayat.ac.ir
Nourallah
Hazeri
Department of Chemistry, Faculty of Sciences, University of Sistan and Baluchestan, Zahedan 98135-674, Iran
nhazeri@chem.usb.ac.ir
10.22036/org.chem.2019.150835.1170
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.
Ascorbic acid,Polyfunctionalized piperidines,Green procedure,Ethanol media,Simple work-up
https://www.orgchemres.org/article_96485.html
https://www.orgchemres.org/article_96485_da520bd42a495a75db32863e4da8989c.pdf
Iranian Chemical Society
Organic Chemistry Research
2383-242X
6
1
2020
06
01
Bis (1(3-trimethoxysilylpropyl)-3-methyl-imidazolium) Nickel Tetrachloride Tethered to Colloidal Silica Nanoparticles as a Superior Catalyst for the Bis-thiazolidinones Preparation
92
99
EN
Javad
Safaei-Ghomi
0000-0002-9837-4478
Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, P.O. Box 87317-51167, I. R. Iran
safaei@kashanu.ac.ir
Seyed Hadi
Nazemzadeh
Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, P.O. Box 87317-51167, I. R. Iran
shnazem@gmail.com
Hossein
Shahbazi-Alavi
Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, P.O. Box 87317-51167, I. R. Iran
hossien_shahbazi@yahoo.com
10.22036/org.chem.2019.191065.1208
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.
Heterogeneous catalysts,Ionic Liquid,Colloidal silica,Bis-thiazolidinones,One-pot
https://www.orgchemres.org/article_99595.html
https://www.orgchemres.org/article_99595_c9dbf40c5ddba8a8a645446941941bbe.pdf
Iranian Chemical Society
Organic Chemistry Research
2383-242X
6
1
2020
06
01
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
100
120
EN
Nader
Noroozi Pesyan
0000-0002-4257-434X
Department of Organic Chemistry, Faculty of Chemistry, Urmia University, 57159, Urmia, Iran
n.noroozi@urmia.ac.ir
F.
Karimi
Department of Organic Chemistry, Faculty of Chemistry, Urmia University, 57159, Urmia, Iran
H.
Batmani
Department of Organic Chemistry, Faculty of Chemistry, Urmia University, 57159, Urmia, Iran
T.
Tunç
Department of Science Education, Faculty of Education, Aksaray University, TR-68100, Aksaray, Turkey
E.
Şahin
Department of Chemistry, Faculty of Science, Atatürk University, TR-25240 Erzurum, Turkey
10.22036/org.chem.2019.189754.1207
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.
1,3-cyclohexanedione,Octahydro-1H-xanthene-1,8(2H)-dione,One-pot,Xanthene,Polymeric H-bond
https://www.orgchemres.org/article_105879.html
https://www.orgchemres.org/article_105879_cbe49e4a7f86f1983331512f739c8929.pdf
Iranian Chemical Society
Organic Chemistry Research
2383-242X
6
1
2020
06
01
3-Methyl-1-sulfonic Acid Imidazolium Mesylate as a Novel, Highly Effective and Dual-functional Catalyst for the Solvent-free Production of Bis-coumarins
121
130
EN
Aseih
Kargar-Dolatabadi
Department of Chemistry, Payame Noor University, P. O. Box 19395-3697, Tehran, Iran.
2920kargarda@gmail.com
Seyed Sajad
Sajadikhah
Department of Chemistry, Payame Noor University, P. O. Box 19395-3697, Tehran, Iran
sssajadi@pnu.ac.ir
Abdolkarim
Zare
Department of Chemistry, Payame Noor University, PO BOX 19395-3697, Tehran, Iran
abdolkarimzare@yahoo.com
Alemeh
Razaghi
Department of Chemistry, Payame Noor University, PO BOX 19395-3697, Tehran, Iran
arazzaghi1@yahoo.com
10.22036/org.chem.2020.184080.1199
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.
Ionic Liquid,3-Methyl-1-sulfonic acid imidazolium mesylate ([Msim][OMs]),Bis-coumarins,Dual-functional catalyst,Solvent-free
https://www.orgchemres.org/article_105880.html
https://www.orgchemres.org/article_105880_c61508e56b5d73348d1b9fef8aa0b9ab.pdf
Iranian Chemical Society
Organic Chemistry Research
2383-242X
6
1
2020
06
01
Aldoses and Ketoses’ Extended Binary and Decimal Numbers: A Logical and Simple Relationship between Name and Structure
131
136
EN
Ahmad
Khorramabadi-zad
0000-0001-6280-3085
Faculty of Chemistry, Bu-Ali Sina University, Hamedan 6517838695, Iran
khoram@gmail.com
Azam
Shiri
0000-0003-4520-2979
Department of Applied Chemistry, Malayer University, Malayer 65719-95863, Iran
amshiri@gmail.com
10.22036/org.chem.2020.184426.1200
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.
Aldose,Ketose,Binary number,Decimal number,Fischer form
https://www.orgchemres.org/article_107410.html
https://www.orgchemres.org/article_107410_cf9178d42b6bc52cf531a2628d5a4c1b.pdf
Iranian Chemical Society
Organic Chemistry Research
2383-242X
6
1
2020
06
01
Friedländer Synthesis of Substituted Quinolines Using an Efficient and Reusable Brønsted Acid Ionic Liquid Supported on Fe3O4@SiO2 Nanoparticles under Solvent-free Conditions
137
149
EN
Mehdi
Fallah-Mehrjardi
Department of Chemistry, Payame Noor University, Tehran, 19395-4697, Iran
fallah.mehrjerdi@pnu.ac.ir
Samaneh
Kalantari
Department of Chemistry, Payame Noor University (PNU), P.O. Box 19395-3697, Tehran, Iran
s.kalantari68@gmail.com
10.22036/org.chem.2020.202084.1217
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.
Magnetic nanoparticles,Supported ionic liquids,Quinolines,Friedländer synthesis,Solvent-free conditions
https://www.orgchemres.org/article_107411.html
https://www.orgchemres.org/article_107411_8efdbefbe554da26f5be22e50732e375.pdf