eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2017-03-01
3
1
1
7
10.22036/org.chem..2017.40875
40875
Synthesis and Photosensitizing Properties of an Activatable Phthalocyanine-Subphthalocyanine Triad
Eveline Vandenwinckel
eveline.vandenwinckel@uam.es
1
Andres de la Escosura
andres.delaescosura@uam.es
2
Tomas Torres
tomas.torres@uam.es
3
Autonoma University of Madrid
Autonoma University of Madrid
Autonoma University of Madrid
In this article, we describe a photosensitizer (PS) whose ability to generate singlet oxygen (1O2) and fluorescence emission has been designed as tumor responsive. More specifically, the PS consists of a silicon phthalocyanine (SiPc) core, axially substituted with two subphthalocyanine (SubPc) units, covalently linked by a disulfide linker, which is cleavable in the presence of a strong reducing agent. Initially, the SubPc units quench the SiPc fluorescent and 1O2-generating properties, most probably by electronic energy transfer. Upon entering a reducing environment, e.g., like those in tumor cells, the disulfide linker would be cleaved and the quenching would be undone, resulting in a sudden generation of 1O2 and a strong fluorescence of both the SiPc and SubPc units. Herein, this behavior has been probed in solution by means of using DTT as the reducing agent that induces the PS activation.
https://www.orgchemres.org/article_40875_95428bc915dddfe8a6159af1951aa739.pdf
Phthalocyanine
Subphthalocyanine
Triad
Photosensitizer
Theranostics
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2017-03-01
3
1
8
15
10.22036/org.chem..2017.40876
40876
One-pot Multi-step Synthesis of some Aromatic Salicylaldoximes Using MgO Nanoparticles
Reza Ranjbar-Karimi
r.ranjbarkarimi@vru.ac.ir
1
Alireza Talebizadeh
a.talebizadeh@vru.ac.ir
2
Manizheh Asadi
karimi_r110@yahoo.com
3
Vali-e-Asr University
Vali-e-Asr University
Vali-e-Asr University
MgO nanopartticels (NP-MgO) in average size between 30—130 nm were prepared by sonochemistry method. Some phenols have been converted to ortho-hydroxybezaldehyd by ortho-formylation using MgO nanoparticles and (CH2O)n in xylene and subsequently treated with aqueous NH2OH.HCl, affording the corresponding aldoxime in a one-pot procedure. Moreover, this one-pot process, with two transformations, offers a number of advantages. In particular, the direct transformation of intermediates to the desired products reduces the time normally spent on isolation and purification.
https://www.orgchemres.org/article_40876_7412e16e54cb0cb41f4b75b00fed5b47.pdf
Aldoxime
MgO nanoparticle
Hydoxylamine
Synthesis
One pot reaction
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2017-03-01
3
1
16
24
10.22036/org.chem..2017.41100
41100
Synthesis of 2-Amino-3,5-dicarbonitrile-6-thiopyridines Using Silica-bonded N-Propyldiethylenetriamine as a Heterogeneous Solid Base Catalyst
Khodabakhsh Niknam
khniknam@gmail.com
1
Alireza Hosseini
ali.hosseini1121@yahoo.com
2
Persian Gulf University
Persian Gulf University
Silica-bonded N-propyldiethylenetriamine (7) is employed as a recyclable heterogeneous solid base catalyst for the synthesis of 2-amino-3,5-dicarbonitrile-6-thiopyridines through pseudo four-component condensation reaction between aromatic aldehydes, malononitrile, and 2-amino-thiophenol in refluxing ethanol. Silica-bonded N-propyldiethylenetriamine showed much the same efficiency when used in consecutive reaction runs.
https://www.orgchemres.org/article_41100_b8519134586b3bb79cb05f3aa49de9dd.pdf
2-Amino-3
5-dicarbonitrile-6-thiopyridines
Heterogeneous catalysts
Solid bases
Synthesis
Multi-component reactions
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2017-03-01
3
1
25
31
10.22036/org.chem..2017.41101
41101
An Effective Green Procedure for the Synthesis of Phenacyl Derivatives Catalyzed by Silica-bound 3-{2-[Poly(ethylene glycol)]ethyl}-substituted 1-Methyl-1H-imidazol-3-ium Bromide as a Recyclable Phase Transfer Catalyst under Aqueous Media
Neda Ayashi
n.aiashy@yahoo.com
1
Mehdi Fallah-Mehrjardi
fallah.mehrjerdi@pnu.ac.ir
2
Ali Kiasat
akiasat@scu.ac.ir
3
Chemistry Department, Collage of Science, Shahid Chamran university of Ahvaz, Ahvaz, Iran
Department of Chemistry, Payame Noor University, Tehran, 19395-4697, Iran
a Chemistry Department, Collage of Science, Shahid Chamran university of Ahvaz, Ahvaz, Iran
The use of a recyclable phase transfer catalyst, SiO2-PEG-ImBr, is demonstrated in a simple and highly efficient synthesis of phenacyl derivatives by nucleophilic substitution reaction of phenacyl halides with different anions in water. Advantages of this system are easy work-up, moderate to good yields, and recyclable catalyst. The catalyst can be recycled and reused several times with no loss of its efficiency.
https://www.orgchemres.org/article_41101_006453ce8148d7bb10ad3f99c7722c9e.pdf
Phenacyl derivatives
Phenacyl halides
Phase transfer catalyst
Nucleophilic substitution
Silica supported
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2017-03-01
3
1
32
36
10.22036/org.chem..2017.50939.1053
47106
Synthesis of Furo[2,3-d]pyrimidine-2,4(1H,3H)-diones From Alcohols Using T3P/DMSO
Ebrahim Soleimani
e_soleimanirazi@yahoo.com
1
Mohammad Mehdi Khodaei
mmkhoda@razi.ac.ir
2
Hossein Yazdani
hosseinyazdani1989@yahoo.com
3
Jafar Mohammad Nejhad
behkia3316@yahoo.com
4
Department of Chemistry, Razi University, Kermanshah 67149-67346, Iran.
Department of Chemistry, Razi University, Kermanshah 67149-67346, Iran.
Department of Chemistry, Razi University, Kermanshah 67149-67346, Iran.
Department of Chemistry, Shahr-e-Qods Branch, Islamic Azad University, Tehran, Iran
T3P/DMSO is shown to be an effective and mild reagent for the one-pot synthesis of furo[2,3-d]pyrimidine-2,4(1H,3H)-diones from a variety of alcohols. Alcohols are oxidized in situ to aldehydes under mild conditions, which undergo a three-component reaction with N,N'-dimethylbarbituric acid and various isocyanides to afford furo[2,3-d]pyrimidine-2,4(1H,3H)-diones in good yields.
https://www.orgchemres.org/article_47106_31aa831a4c2a39f14357e46655c8110e.pdf
Furo[2
3-d]pyrimidine
T3P/DMSO
Oxidization
Isocyanide
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2017-03-01
3
1
37
43
10.22036/org.chem.2017.75197.1084
48971
Fe(HSO4)3-Catalyzed Direct Conversion of Aldehydes into Nitriles Using Hydroxylamine Hydrochloride
Hassan Taheri
taheri.hassan56@gmail.com
1
Ali Shiri
alishiri@um.ac.ir
2
Hossein Eshghi
heshghi@um.ac.ir
3
Seddigheh Sheikhi-Mohammareh
s.sheikhi_6687@yahoo.com
4
Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, 91775-1436 Mashhad, Iran.
Ferdowsi University of Mashhad
Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad
Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, 91775-1436 Mashhad, Iran.
Due to the importance and various applications of nitriles especially in medicinal productions, a new method for conversion of aldehydes to nitriles has been presented. Several nitrile-containing aromatic compounds were synthesized through the treatment of various aldehydes and hydroxylamine hydrochloride as nucleophile in the presence of ferric hydrogen sulfate as a heterogeneous, efficient, and recyclable catalyst in DMF in good to excellent yields.
https://www.orgchemres.org/article_48971_99615c8906d51250df0800ec70cf375f.pdf
hydroxylamine hydrochloride
Ferric hydrogen sulfate
Nitriles
Aldehydes
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2017-03-01
3
1
44
49
10.22036/org.chem.2017.58765.1070
49037
One-pot Efficient Oximation-Beckmann Rearrangement of Ketones Catalyzed by Fe3O4 Under Solvent-free Conditions
Ehsan Ghonchepour
ghonchepoor@gmail.com
1
Dariush Saberi
dariushsaberi2000@gmail.com
2
Akbar Heydari
heydar_a@modares.ac.ir
3
student
associate professor
professor
Fe3O4 nanoparticles were employment as an efficient and magnetically separable Nano catalyst for the synthesis of amides via one-pot Beckmann rearrangement of ketones under solvent-free conditions. Various secondary amides were synthesized by this method in moderate to good yields. The catalyst showed high thermal stability and was recovered and reused at least five times without any considerable loss of activity. The present process is environmentally benign and economical
https://www.orgchemres.org/article_49037_031d30d1a948f0dfa708bb3c5c62907c.pdf
Magnetic
Beckmann rearrangement
Green catalyst
Ketones
Fe3O4
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2017-03-01
3
1
50
60
10.22036/org.chem.2017.60487.1076
49193
Basic Task-specific Ionic Liquid as Catalyst and Reaction Medium: A Green Protocol for the Synthesis of 4-Oxo-6-aryl-2-thioxo-1,2,3,4- tetrahydropyrimidine-5-carbonitrile Derivatives
Maede Hasanpour
md.hasanpour@gmail.com
1
Hossein Eshghi
heshghi@um.ac.ir
2
Mahdi Mirzaei
mirzaei125@yahoo.com
3
Department of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad, Mashhad 91775-1436, Iran
1Department of Chemistry, School of Sciences, Ferdowsi University of Mashhad, 91775-1436 Mashhad, Iran
Department of Chemistry, School of Sciences, Ferdowsi University of Mashhad, 91775-1436 Mashhad, Iran
Abstract A novel basic ionic liquid based on imidazolium cation is designed, synthesized and successfully used as a catalyst for the one-pot synthesis of 4-Oxo-6-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile derivatives. The remarkable features of this new catalyst are its ethyleneoxy bridge which participates in dissolving organic compound in the ionic liquid and its strong base counterion. The application of this ionic liquid is studied in a new one-pot method for the synthesis of heterocyclic compounds under solvent-free conditions. A simple and convenient procedure, high conversion, reusability of catalyst, easy purification and shorter reaction time are the advantageous features of this method.
https://www.orgchemres.org/article_49193_cef7fa1282aa8b47945d7d44333e0c2d.pdf
Ionic Liquid
Imidazolium cation
Pyrimidine
Reusable catalyst
Ethyleneoxy bridge
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2017-03-01
3
1
61
72
10.22036/org.chem.2017.83905.1092
50653
Conventional and Unconventional Intramolecular Hydrogen Bonding in some Beta-diketones
Vahidreza Darugar
vahidrezadarugar@gmail.com
1
Mohammad Vakili
vakili-m@um.ac.ir
2
Raheleh Afzali
afzalimona@yahoo.com
3
Sayyed Faramarz Tayyari
sftayyari@yahoo.com
4
Department of Chemistry, Ferdowsi University of Mashhad, Mashhad 91775-1436, Iran
Department of Chemistry, Ferdowsi University of Mashhad, Mashhad 91775-1436, Iran
Department of Chemistry, Ferdowsi University of Mashhad, Mashhad 91775-1436, Iran
Department of Chemistry, Ferdowsi University of Mashhad, Mashhad 91775-1436, Iran
This study presents our view of unconventional and conventional intramolecular hydrogen bonds (HBs) for some beta-diketones theoretically and experimentally. According to our results, the groups such as Phenyl and t-But in beta positions increase and CF3 group decrease IHB strength, respectively. For better understanding of the substitution effects, the compounds with similar and different substitutions compared to each other experimentally and theoretically. Comparison between theoretical and experimental results, EHB and OH, show, by adding one substitution, these parameters change, which by adding another similar substitution, these changing approximately doubled. This conclusion achieved for DMPD, with phenyl and t-But groups in beta positions. Whereas, TFBA, with phenyl and CF3 groups, and TFDMHD, with CF3 and t-But groups in beta positions, don’t follow this achievement. The 1HNMR chemical shifts for the stable cis-enol forms of the mentioned compounds have been calculated at different levels with various basis sets in CHCl3 as solvent by using PCM method. For the most beta-diketones, the 6-311G** and 6-311++G** basis sets, in all our calculated levels, are in better agreement with the experimental results. According to AIM results, unconventional hydrogen bonding created in some beta-diketones, which have Ph group. The strength of this hydrogen bonding for these compounds are same and about 2 kcal/mol.
https://www.orgchemres.org/article_50653_83f56ff7b0faab12ea685de1c0d230da.pdf
β-diketones
DFT
Conventional and unconventional intramolecular hydrogen bond
Atoms In Molecules Theory
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2017-03-01
3
1
73
85
10.22036/org.chem..2017.57492.1068
50688
A Tandem Scalable Microwave-Assisted Williamson Alkyl Aryl Ether Synthesis under Mild Conditions
Mohammad Javaherian
m.javaherian@scu.ac.ir
1
Foad Kazemi
kazemi_f@iasbs.ac.ir
2
Sayed Ebrahim Ayati
ayati1984@yahoo.com
3
Jamal Davarpanah
jamaldavarpanah@gmail.com
4
Mousa Ramdar
m.ramdar@iasbs.ac.ir
5
Shahid Chamran University of Ahvaz
University for Advanced Studies in Basic Sciences, Zanjan
University for Advanced Studies in Basic Sciences, Zanjan
University for Advanced Studies in Basic Sciences, Zanjan
University for Advanced Studies in Basic Sciences, Zanjan
An efficient tandem synthesis of alkyl aryl ethers, including valuable building blocks of dialdehyde and dinitro groups under microwave irradiation and solvent free conditions on potassium carbonate as a mild solid base has been developed. A series of alkyl aryl ethers were obtained from alcohols in excellent yields by following the Williamson ether synthesis protocol under practical mild conditions. Scale up ability of this practical procedure is shown by the preparation of some of the valuable dialdehydes up to 50 mmole from alcohols. The method is simple, rapid, straight-forward and holds potential for further application in organic synthesis and industrial requirements.
https://www.orgchemres.org/article_50688_0c5e94e460a9af034cecfdaa372fa616.pdf
Tandem
scalable
Williamson ether synthesis
Alkyl tosylate
Microwave irradiation
Bis-2-nitrophenoxy akyl ether
Bis-2-formylphenoxy alkyl ether
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2017-03-01
3
1
86
94
10.22036/org.chem.2017.58134.1069
50692
Photochemical, Solvatochromic, Electrochromic and Kinetic Investigation of New Synthesized Bicyclic Aziridines with Chalcone Moieties
Nosratollah Mahmoodi
mahmoodi@guilan.ac.ir
1
Tayebeh Besharati-Seidani
t.besharati@yahoo.com
2
A. Aliakbar
3
B. Ghalami Choobar
4
Department of Chemistry, Faculty of Science, University of Guilan, P.O. Box: 41335-1914, Rasht, Iran
Department of Chemistry, Faculty of Science, University of Guilan, P.O. Box: 41335-1914, Rasht, Iran
Department of Chemistry, Faculty of Science, University of Guilan, P.O. Box: 41335-1914, Rasht, Iran
Department of Chemistry, Faculty of Science, University of Guilan, P.O. Box: 41335-1914, Rasht, Iran
Bicyclic aziridines show exclusive photochromic behavior. Here, we summarize the results of optical and electrochemical properties, such as photochemical, solvatochromic, electrochromic andkinetic behavior of bicyclic aziridines linked to chalcone moieties. The photochromic process for conversion of closed photoisomers to open photoisomers for compounds 1-10 followed zero-order kinetics. For considering the solvatochromic properties of compounds 1,3,5,7 and 9, photochromic properties of these compounds in different solvents were investigated and the negative solvatochromism were observed. The redox behavior of several derivatives of bicyclic aziridines by cyclic voltammetry was examined for compounds 1,3,5 and 6, and irreversible oxidation was observed.
https://www.orgchemres.org/article_50692_b05cdd280a30960cdd7b58627f9c025c.pdf
Bicyclicaziridine
Chalcone
1
3-Diazabicyclo[3.1.0]hex-3-enes
Photochromism
Solvatochromism
Cyclic Voltammetry
eng
Iranian Chemical Society
Organic Chemistry Research
2383-242X
2017-03-01
3
1
95
102
10.22036/org.chem..2017.79473.1087
50693
Layered Double Hydroxides (LDHs): An Efficient Catalyst System for the Synthesis of Chiral Aminonitriles
Fatemeh Tahoori
f.tahoori@rvsri.ac.ir
1
Mona Moradinejad
mmoradinejad24@gmail.com
2
Reza Tondfekr
rtondfekr@student.unimelb.edu.au
3
Farnaz Karbasi
fkarbasi@iauet.ac.ir
4
Razi Vaccine and Serum Research Institute, Agricultural Research and Extension Organization (AREEO), Karaj, Iran
Department of Chemistry, Tehran East branch, Islamic Azad University, Tehran, Iran
Department of Chemistry, Iran University of Science and Technology, Tehran, Iran
Department of Chemistry, Tehran East branch, Islamic Azad University, Tehran, Iran
Strecker reaction is one of the simplest multicomponent reactions. It used for synthesis of chiral α-amino nitriles. This reaction was carried out in the presence of catalytic amount of layered double hydroxides (LDHs). In this study, simple and practical method for the synthesis of this class of catalysts is provided. The results shown that LDH is the good heterogen catalyst for synthesis of chiral α-amino nitriles.
https://www.orgchemres.org/article_50693_1e31dd139e31a9529cba7e688278049b.pdf
Layered double hydroxide (LDHs)
Strecker reaction
α-Amino acids
Diastereoselectivity