eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2018-09-24
5
1
1
9
10.22036/org.chem.2018.130876.1142
69578
Chemoselective N-tert-butoxycarbonylation and N-formylation of Amines by B(OSO3H)3/SiO2 as an Efficient Heterogeneous and Recyclable Catalyst
Hosein Hamadi
h.hammadi@scu.ac.ir
1
Maryam Gholami
mrygholami@yahoo.com
2
Shahid Chamran University of Ahvaz
Chemistry Department, Faculty of Sciences, Shahid Chamran University of Ahvaz
A simple, efficient, and cost-effective procedure for the N-tert-butoxycarbonylation and N-formylation of amines (primary, secondary) respectively, with di-tert-butyl dicarbonate and 85% aqueous formic acid under solvent-free condition using B(OSO3H)3/SiO2 (SBSA) as a heterogeneous and recyclable catalyst has been developed. We demonstrated that the resulting catalyst is applicable to various aromatic and aliphatic amines giving excellent yields of the desired products in short reaction time (
https://www.orgchemres.org/article_69578_6e25b0c54f69e1c9eb9134b47cba84ca.pdf
Protection
Boc
Formylation
Catalyst
B(OSO3H)3
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2019-09-01
5
1
10
24
10.22036/org.chem.2018.121576.1132
69579
Immobilized Palladium-pyridine Complex on γ-Fe2O3 Magnetic Nanoparticles as a New Magnetically Recyclable Heterogeneous Catalyst for Heck, Suzuki and Copper-free Sonogashira Reactions
Sara Sobhani
sobhanisara@yahoo.com
1
Samira Esmaeilzadeh-Soleimani
samiesmaeil@yahoo.com
2
Department of Chemistry, College of Sciences, University of Birjand, Birjand, Iran
Department of Chemistry, College of Sciences, University of Birjand, Birjand, Iran
A new immobilized palladium-pyridine complex on γ-Fe2O3 magnetic nanoparticles was synthesized and characterized by SEM, TEM, TGA, ICP, XPS, XRD, FT-IR and CHN analysis. The catalytic activity of synthesized catalyst has been investigated in Heck, Suzuki and Sonogashira coupling reactions using a series of aryl halides. The catalyst was easily isolated from the reaction mixture by an external magnetic field and reused several times with no significant loss of catalytic activity.
https://www.orgchemres.org/article_69579_80f63f2e06a25d6828c0190fc7e65adb.pdf
Palladium
Iron oxide
Coupling reactions
Heterogeneous catalyst
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2019-09-01
5
1
25
31
10.22036/org.chem.2018.126182.1137
69580
Mild and Solvent-free Synthesis and Antibacterial Evaluation of Novel Sulfonamides Containing Hydroxyl Groups
Ahmad Reza Massah
massah@iaush.ac.ir
1
Seyedeh Simin Dakhilpour
dakhilpour.simin@gmail.com
2
Sara Ebrahimi
s_gorjia60@yahoo.com
3
Saeed Naseri
naseri.pharma@gmail.com
4
Mina Nateghi
nateghi.mina@yahoo.com
5
Departrment of Chemistry, Shahreza Branch, Islamic Azad University
Department of Chemistry,Shahreza Branch, Islamic azad University,
Department of Chemistry, Shahreza Branch, Islamic Azad University
Department of Chemistry, Shahreza Branch, Islamic Azad University
Department of Chemistry, Shahreza Branch, Islamic Azad University
A series of interesting sulfonamides containing hydroxyl group were synthesized under solvent-free conditions. The synthetic route involves the selective reaction of amino alcohol and sulfonating agents. The sulfonamides were obtained by simple procedure after an easy work-up in high yield and purity, and characterized by IR, 1H NMR and 13C NMR analysis. These compounds were tested for antibacterial activity against four bacterium including Escherichia Coli, Staphylococcus Aurous, Bacillus Subtilis and Salemonella Typhi.
https://www.orgchemres.org/article_69580_d18060c30a6c0e929ff62a8a2cdc8a1a.pdf
Sulfonamide
Solvent-free
antibacterial
Amino alcohol
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2019-09-01
5
1
32
41
10.22036/org.chem.2018.118054.1124
69676
An Experimental Study to Biological Activity and Synthesis; and Theoretical Study for MEP, HOMO/LUMO Analysis and Molecular Docking of N-(2-pyridyl)-para-styrene Sulfonamides
Parvaneh Shafieyoon
parva127@yahoo.com
1
Ebrahim Mehdipour
e_mehdipour@yahoo.com
2
Hosien Tavakol
hosein_ta@yahoo.com
3
Department of Chemistry, Faculty of Science, Lorestan University, Khoramabad
Department of Chemistry Faculty of Science Lorestan University, 68137-17133 Khorramabad Iran
Department of Chemistry, Isfahan University of Technology
A combined experimental and theoretical investigation has been reported on N-(2-pyridyl)-para-styrene sulfonamide (abbreviated as PSS). This compound synthesized from the reaction of para-styrene sulfonyl chloride and 2- amino pyridine. The PSS was confirmed using FT-IR, 1H-NMR spectroscopy. MEP and HOMO-LUMO analysis of the PSS have been investigated using DFT method. The PSS is investigated against Staphylococcus aureus and Escherichia coli. Molecular Docking study is also reported.
https://www.orgchemres.org/article_69676_4b2711430d7a3271255fe25ce40de3e2.pdf
N-(pyridyl)-para styrene sulfonamide
DNA
BSA
MEP
HOMO and LUMO analysis
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2019-09-01
5
1
42
50
10.22036/org.chem.2018.133516.1150
69689
Synthesis of New 2-Azetidinone Derivatives and Related Schiff Bases from 3-Phenyl-2,3,6,7-tetrahydroimidazo [2,1-b] Thiazolo [5,4-d] Isoxazole
Hamid Reza Jaberi
h_r_jaberi@yahoo.com
1
Hanif Fattahi
2
Arman Ahmannasrollahi
3
Mohammadreza Yarandpour
4
Sharareh Sedaghatizadeh
5
Department of Production, Aburaihan Pharmaceutical Co., Tehran, Iran; R&D Division, Aburaihan Pharmaceutical Co., Tehran, Iran
Department of Production, Aburaihan Pharmaceutical Co., Tehran, Iran; R&D Division, Aburaihan Pharmaceutical Co., Tehran, Iran
Department of Production, Aburaihan Pharmaceutical Co., Tehran, Iran
Department of Production, Aburaihan Pharmaceutical Co., Tehran, Iran
Department of Production, Aburaihan Pharmaceutical Co., Tehran, Iran
2-Azetidinones, commonly known as β-lactams, are well-known heterocyclic compounds. Herein we described the synthesis of a series of novel β-lactams. The efficient and rapid synthesis of novel β-lactams has been established in good yields starting from (R)-3-phenyl-2, 3, 6, 7-tetrahydroimidazo [2', 1':2, 3] thiazolo [5, 4-d] isoxazole 1. First, (R)-3-phenyl-2, 3, 6, 7-tetrahydroimidazo [2', 1':2, 3] thiazolo [5, 4-d] isoxazole 1 on condensation with ethylchloro acetate yielded Ethyl (R) 2-(3-phenyl- 6, 7-dihydroimidazo [2', 1':2,3] thiazolo [5, 4-d] isoxazole-2(3H)-yl) acetate 2, which on amination with hydrazine hydrate yielded (R) 2-(3-phenyl- 6, 7-dihydroimidazo [2', 1':2, 3] thiazolo [5, 4-d] isoxazol -2(3H)-yl) acetohydrazide 3. Then, condensation between compound 3 and various aromatic aldehydes give Schiff base derivatives 4a-j, which upon dehydrative annulation in the presence of chloroacetyl chloride and triethylamine yielded N-((3S, 4S)-3-chloro-2-oxo-4-phenylazetidin-1-yl)-2-((R)-3-(Aryl)-6, 7-dihydroimidazo [2', 1':2, 3] thiazolo [5, 4-d] isoxazol -2(3H)-yl) acetamide 5a-j. All synthesized compounds were characterized by elemental analyses, IR, 1H-NMR and 13C-NMR data.
https://www.orgchemres.org/article_69689_430737cf607b9e1584cb5d3ab0af5962.pdf
Condensation
Synthesis
Schiff bases
2-Azetidinones
β-Lactam
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2019-09-01
5
1
51
63
10.22036/org.chem.2018.134334.1155
76914
3-(Propylcarbamoyl)acrylic Acid Functionalized Magnetic Nanoparticles Grafted to Poly (N-isopropylacrylamide-co-Acrylic Acid) Hydrogel: LCST and Drug Release
Ali Reza Karimi
a-karimi@araku.ac.ir
1
Zeinab Tajabadi
z2000.farahani@gmail.com
2
Azam Khodadadi
n.khodadadi65@gmail.com
3
Fereshteh Abdi
abdi9090@yahoo.com
4
Department of Chemistry, Faculty of Science, Arak University, Arak 38156-8-8349, Iran
Department of Chemistry, Faculty of Science, Arak University, Arak 38156-8-8349, Iran
Department of Chemistry, Faculty of Science, Arak University, Arak 38156-8-8349, Iran
Department of Chemistry, Faculty of Science, Arak University, Arak 38156-8-8349, Iran
In this research, to overcome the low mechanical properties of hydrogels based on Poly N-isopropylacrylamide (PNIPAAm) and improve their stimuli responsive behavior and lower critical solution temperature LCST, a new kind of hybrid magnetic nanoparticles was designed and prepared and then grafted to (PNIPAAm-co-AAc) hydrogel through in situ dispersion copolymerization route. 3-(propylcarbamoyl)acrylic acid functionalized silica-coated magnetic nanoparticles (PC-AAc/MNPs) was prepared and used as a template for in situ dispersion copolymerization of the poly N-isopropylacrylamide (PNIPAAm) and acrylic acid (AAc) in the presence of methylene-bis-acrylamide as a cross-linking agent via free radical cross-linking polymerization. Also, controlled drug release behavior of metronidazole was investigated with prepared nanocomposite hydrogels. The vibrating sample magnetometer (VSM) illustrated superparamagnetic behavior for (PC-AAc/MNPs) and nanoparticles grafted hydrogel. Scanning electron microscopy (SEM) image of functionalized magnetic nanoparticles showed that they are spherical in shape and have the spherical structure with a diameter of about 15-30 nm. Moreover, the lower critical solution temperature (LCST) of the (PC-AAc/MNPs-g-PNIPAAm-co-AAc) hydrogel, as well as the onset temperatures, measured by the cloud point (CP) method at ~ 42 C. Combined magnetic properties and thermosensitive behavior of (PNIPAAm-co-AAc) grafted magnetic nanoparticles could be utilized in controlled drug-targeting delivery. Hence, metronidazole as a model drug loaded on the magnetic hydrogel nanocomposite and the amount of drug release was measured by UV-Vis spectroscopy.
https://www.orgchemres.org/article_76914_6c513ee3fa3e4326e3ac2e27d3656fb0.pdf
Magnetic polymer
hydrogels
Nanocomposites
Drug delivery systems
LCST
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2019-09-01
5
1
64
72
10.22036/org.chem.2018.109157.1117
76916
Synthesis of Quinazolinone Derivatives through Multicomponent/Click Reactions
Ghodsi Mohammadi Ziarani
gmziarani@hotmail.com
1
Seyedeh Yasaman Afsar
yasaman_afsar@yahoo.com
2
Parisa Gholamzadeh
gholamzadehparisa94@gmail.com
3
Alireza Badiei
abadiei@khayam.ut.ac.ir
4
Alzahra University
Chemistry, Alzahra University
Chemistry, Alzahra university
University of Tehran
Quinazolinones were synthesized through the one-pot three-component reaction of aromatic aldehydes, isatoic anhydride, and urea under solvent-free conditions using sulfonic acid functionalized mesoporous silica (SBA-Pr-SO3H). The propargyl ether containing 2,3-dihydroquinazolin-4(1H)-ones were reacted with sodium azide in the presence of CuI to gain the new triazole-quinazolinone products.
https://www.orgchemres.org/article_76916_f4e60c398ea1c80a34b7e495e9af1651.pdf
Dihydroquinazolinone
Quinazolinone
SBA-Pr-SO3H
Click reaction
Isatoic anhydride
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2019-09-01
5
1
73
79
10.22036/org.chem.2018.130893.1143
76917
A Simple and Efficient Method for the Synthesis of 2,3,5,6-Tetrachloro-4- iodopyridine, and its Reactivity Toward Hard and Soft Nucleophiles
Reza Ranjbar-Karimi*
r.ranjbarkarimi@vru.ac.ir
1
Tayebeh Davoodian
t.davodian83@yahoo.com
2
Alireza Poorfreidoni
alireza_poorfreidoni@yahoo.com
3
Hossein Mehrabi
mehraby_h@yahoo.com
4
Department of Chemistry, Faculty of Science, Vali-e-Asr University, Rafsanjan 77176, Islamic Republic of Iran
Department of Chemistry, Faculty of Science, Vali-e-Asr University, Rafsanjan 77176, Islamic Republic of Iran
Department of Chemistry, Faculty of Science, Vali-e-Asr University, Rafsanjan 77176, Islamic Republic of Iran
Department of Chemistry, Faculty of Science, Vali-e-Asr University, Rafsanjan 77176, Islamic Republic of Iran
2,3,5,6-tetrachloro-4-iodopyridine was successfully synthesized in one-step from the reaction of pentachloropyridine with sodium iodide using microwave irradiation. The reaction of O, N, and S centered nucleophiles with 2,3,5,6-tetrachloro-4-iodopyridine was studied in order to assess regiochemistry of aromatic nucleophilic substitution. Substitution occurs at the para position to ring nitrogen by S centered nucleophiles, while O and N centered nucleophiles substitution occurs at the ortho position of pyridine ring. IR, 1H NMR, and 13C NMR spectroscopy, confirmed the structures of all the compounds.
https://www.orgchemres.org/article_76917_b897989d53918787d4786406934687af.pdf
Pentachloropyridine
Tetrachloro-4-iodopyridine
Regiochemistry
Microwave
Heterocycle
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2019-09-01
5
1
80
86
10.22036/org.chem.2018.134699.1158
76918
Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones Promoted by Polystyrene Sulfonic Acid
zahra zaghaghi
zzaghaghi@yahoo.com
1
Bi Bi Fatemeh Mirjalili
fmirjalili@yazd.ac.ir
2
Azam Monfared
dmonfared@gmail.com
3
Payame Noor University
Yazd University
Departmentb of Chemistry, Tehran Centre branch, Payam-e-Noor University, Tehran, IRAN
In this research, we have synthesized polystyrene sulfonic acid as a new heterogeneous solid acid. Then, we have synthesized 2,3-dihydroquinazolin-4(1H)-ones via condensation of 2-aminobenzamide and different aldehydes in the presence of polystyrene sulfonic acid. The major advantages of the present method are good yields, ecofriendly and easy work-up.
https://www.orgchemres.org/article_76918_afc58774299b4d3a32e056f0fabf0e6a.pdf
Synthesis of 2
3-Dihydroquinazolin-4(1H)-ones
Polystyrene sulfonic acid
Heterogeneous catalyst
2-Aminobenzamide
Solid acid
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2019-09-01
5
1
87
94
10.22036/org.chem.2018.133272.1148
79186
Synthesis of New Benzothiazole Derivatives and Evaluation of Cytotoxicity of N-(6-Substitued-1,3-benzothiazol-2-yl)-4-phenyl-1,3-thiazol-2(3H)-imine Compounds
Hossein Eshghi
heshghi@um.ac.ir
1
Fatemeh Eshkil
f.eshkil@gmail.com
2
Amir SHokooh Saljooghi
saljooghi@um.ac.ir
3
Mehdi Bakavoli
mbakavoli@um.ac.ir
4
Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad
Department of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad, 91775-1436 Mashhad, Iran
Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran
Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran
Cyclization of unsymmetrical thioureas affords N-(6-substitued-1,3-benzothiazol-2-yl)-4-phenyl-1,3-thiazol-2(3H)-imine compounds by the reaction of 1-(1,3-benzothiazol-2-yl)thiourea derivatives and 2-bromoacetophenone in the presence of Et3N. Also, methyl-1,3-benzothiazol-2-yl carbamodithioate derivatives with methyl anthranilate were reacted and 3-(benzo[d]thiazol-2-yl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives as new compounds are synthesized. In the following, synthesized compounds (2a- 2d) were evaluated for anti-tumor activity against MCF-7, MAD-MD-231, HT-29, HeLa, Neuro-2a, K-562 and L-929 cell lines and the results obtained from MTT-assay revealed the best cytotoxicity for 2b compound containing a phenolic segment in their buildings. On the other hand, apoptosis assay for this compound was also carried out by flow cytometry supporting the other results.
https://www.orgchemres.org/article_79186_b8ba449dbb668c3473cd1391647e3844.pdf
Unsymmetrical thioureas
MTT-assay
Flow Cytometry
TUNEL assay
1-(1
3-benzothiazol-2-yl)thiourea
3-(benzo[d]thiazol-2- yl)-2-thioxo-2
3-dihydroquinazolin-4(1H)-one
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2019-09-01
5
1
95
104
10.22036/org.chem.2018.132367.1146
80654
A Facile Three-component Green Synthesis of Polyhydroacridines Using Fe3+@mont-modified Montmorillonite
Manouchehr Mamaghani
m-chem41@guilan.ac.ir
1
Sarvin Yazdanfar
yazdanfarsarvin@gmail.com
2
Roghayeh Hossein Nia
hosseinnia.h@gmail.com
3
University of Guilan
Department of Chemistry, Faculty of Sciences, University of Guilan
Department of Chemistry, Faculty of Sciences, University of Guilan
In this report a green strategy for the synthesis of polyhydroacridine derivatives via one-pot three-component coupling reaction of arylaldehydes, 1,3-cyclohexanedione and aniline derivatives in the presence of modified montmorillonite (Fe3+@mont.) as heterogeneous and reusable catalyst under solvent-free conditions was developed. The reaction in the presence of this catalyst furnished the desired products in short reaction times (10-15 min.) and high to excellent yields (78-98%).
https://www.orgchemres.org/article_80654_e19faf91ab432f16ea826d4d42efd3ca.pdf
Polyhydroacridine
1
4-Dihydropyridine
Fe3+@mont
Solvent-free
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2019-09-01
5
1
105
111
10.22036/org.chem.2018.133755.1151
80754
Triethylaminium-N-sulfonic Acid Tetrachloroaluminate (TSAT) as a New Ionic Liquid Catalyst for the Synthesis of [1,2,4]Triazolo[1,5-a]pyrimidines
Aseih Kargar
2920kargarda@gmail.com
1
Seyed Sajad Sajadikhah
sssajadi@pnu.ac.ir
2
Abdolkarim Zare
abdolkarimzare@yahoo.com
3
Department of Chemistry, Payame Noor University (PNU), 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
Triethylaminium-N-sulfonic acid tetrachloroaluminate (TSAT) as a new ionic liquid was synthesized and characterized by its FT-IR, 1H, 13C NMR and mass spectra as well as TG and DTG diagrams. This ionic liquid was employed as a catalyst for the synthesis of [1,2,4]triazolo[1,5-a]pyrimidines-6-carboxamides via one-pot three-component reaction of aromatic aldehydes, acetoacetanilide and 3-amino-1,2,4-triazole under solvent-free conditions at 60 °C .The salient features of the present protocol are mild reaction condition, easy isolation of products and clean reaction profiles.
https://www.orgchemres.org/article_80754_253f7bddcf95d873a84bb31add753e23.pdf
Ionic Liquid
Triethylaminium-N-sulfonic acid tetrachloroaluminate (TSAT)
[1
4]Triazolo[1
5-a] pyrimidines-6-carboxamide
Acetoacetanilide
3-Amino-1
2
4-triazole