Iranian chemical communication

Organic chemistry

A facile and efficient synthesis of Baclofen

Ali Saberi

Volume 4, Issue 2, pp. 133-235, Serial No. 11 , April 2016, , Pages 142-145

Abstract

  γ-Aminobutiric acid (GABA), the major inhibitory neurotransmitter in the central nervous system is activated by the antispastic and muscle relaxant agent, Baclofen, which is a lipophilic derivative of GABA. Because of its biological and pharmacological importance, there are several reports in the ...  Read More γ-Aminobutiric acid (GABA), the major inhibitory neurotransmitter in the central nervous system is activated by the antispastic and muscle relaxant agent, Baclofen, which is a lipophilic derivative of GABA. Because of its biological and pharmacological importance, there are several reports in the literature about the synthesis of baclofen since 1962. In this study baclofen was easily synthesized by Claisen condensation of ethyl acetoacetate and p-chlorobenzaldehyde, formation of cyclic imide from β(p-chlorophenyl) glutaric acid and further Hoffmann rearrangement of β(p-chlorophenyl) glutarimid. Reagents used were inexpensive and commercially available. The overall yield of the reported strategy was 50% which is a good yield compare with other previous reports.

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Organic chemistry

Isolation and identification of gallic acid from the elaeagnus angustifolia leaves and determination of total phenolic, flavonoids contents and investigation of antioxidant activity

Abdolreza Abri; Mojgan Maleki

Volume 4, Issue 2, pp. 133-235, Serial No. 11 , April 2016, , Pages 146-154

Abstract

  Elaeagnus angustifolia has many potential applications in drugs, detergents, perfumes, herbal teas and show various biological and pharmacological activities, such as anti-inflammatory, antipyretic and other effective treatment of disease. Gallic acid (GA) and its derivative methyl gallate (MG) are well ...  Read More Elaeagnus angustifolia has many potential applications in drugs, detergents, perfumes, herbal teas and show various biological and pharmacological activities, such as anti-inflammatory, antipyretic and other effective treatment of disease. Gallic acid (GA) and its derivative methyl gallate (MG) are well studied plant phenolics. They have exhibited anticancer effects in several cancer cell lines. In the present work, The E. angustifolia leaves were collected from the enclosure of Azerbaijan Shahid Madani University trees and were dried in the shade condition, were milled and extracted successively with n-hexane, ethyl acetate and methanol in a Soxhlet apparatus for 24 h. Further study on the methanol extract of this plant has resulted in the isolation of gallic acid. The structure of the compound was established by spectroscopic methods. Antioxidant properties of flavonoid and phenolic compoundes were measured.

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Organic chemistry

One-pot, four-component synthesis of fully substituted 1,3,4-oxadiazole derivatives from N-isocyaniminotriphenylphosphorane (Ph3PNNC), a primary amine, a carboxylic acid and cinnamaldehyde

Fatemeh Kalantari; Ali Ramazani; Fatemeh Zeinali Nasrabadi

Volume 4, Issue 2, pp. 133-235, Serial No. 11 , April 2016, , Pages 155-164

Abstract

  The imine intermediate generated by the addition of primary amine to the cinnamaldehyde is trapped by the N-isocyaniminotriphenylphosphorane (Ph3PNNC) and a carboxylic acid, and leads to the formation of the corresponding iminophosphorane intermediate. The 1,3,4-oxadiazole derivatives are formed via ...  Read More The imine intermediate generated by the addition of primary amine to the cinnamaldehyde is trapped by the N-isocyaniminotriphenylphosphorane (Ph3PNNC) and a carboxylic acid, and leads to the formation of the corresponding iminophosphorane intermediate. The 1,3,4-oxadiazole derivatives are formed via intramolecular aza-Wittig reaction of the iminophosphorane intermediate. The reactions were completed under neutral conditions at room temperature. The fully substituted 1,3,4-oxadiazole derivatives were produced in high yields. The method offers a mild, simple, and efficient route for the preparation of fully substituted 1,3,4-oxadiazols. The structures of the products were deduced from their IR, 1H NMR, 13C NMR spectra, and mass spectrometry.

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Organic chemistry

Synthesis and characterization of some polymer derivatives of carvacrol as drug delivery system

Mohammad Galehassadi; Ebrahim Rezaii

Volume 4, Issue 2, pp. 133-235, Serial No. 11 , April 2016, , Pages 165-174

Abstract

  Carvacrol is one of the main components of the EO of some Labiatae (Laminaceae) members like oregano, thyme and savory. Carvacrol has a lot of health benefits for example, antibacterial, and antioxidant activity.We synthesized some silicon derivatives of carvacrol, and characterized them by standard ...  Read More Carvacrol is one of the main components of the EO of some Labiatae (Laminaceae) members like oregano, thyme and savory. Carvacrol has a lot of health benefits for example, antibacterial, and antioxidant activity.We synthesized some silicon derivatives of carvacrol, and characterized them by standard methods. Then the monomer of dimethylvinylsilyl carvacrol was synthesized. Copolymer of this monomer and methacrylic acid (MAA) was synthesized with different ratios. And releases of these polymers as an drug delivery systems were investigated in the pH = 1 pH = 7.4.In this way , we stnthesized a new sily polymer with base of drug delivery system for a phytochemical compound.

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Organic chemistry

Microwave-assisted synthesis of 5,10,15,20-tetrakis(4-nitrophenyl)porphyrin and zinc derivative and study of their bacterial photoinactivation

Rahmatollah Rahimi; Fatemeh Fayyaz; Mehdi Rassa; Mahboubeh Rabbani

Volume 4, Issue 2, pp. 133-235, Serial No. 11 , April 2016, , Pages 175-185

Abstract

  In this study, 5,10,15,20-tetrakis(4-nitrophenyl)porphyrin (TNPP) and its zinc porphyrin complex (ZnTNPP) were synthesized in situ using the microwave method and identified by UV-Vis, FT-IR and 1H NMR. The photostability and photodynamic antimicrobial activity (PACT) of these compounds were investigated ...  Read More In this study, 5,10,15,20-tetrakis(4-nitrophenyl)porphyrin (TNPP) and its zinc porphyrin complex (ZnTNPP) were synthesized in situ using the microwave method and identified by UV-Vis, FT-IR and 1H NMR. The photostability and photodynamic antimicrobial activity (PACT) of these compounds were investigated on Pseudomonas aeruginosa and Bacillus subtilis under visible light irradiation. MIC, MBC and inhibition zones produced by these compounds were determined and the number of bacteria counted. The results indicated that both compounds have significant stability when illuminated for various illumination periods in nutrient broth media. Both compounds exhibited more effective activity against P. aeruginosa than B. subtilis in nutrient agar.

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Organic chemistry

Tetrabutylammonium bromide-Cesium carbonate: new reagent system for the synthesis of substituted pyridines at room temperature

Vinod Kamble; Sandeep Atkore; Parshuram Pisal; Munazza Sadaf; Renuka V. Thakre

Volume 4, Issue 2, pp. 133-235, Serial No. 11 , April 2016, , Pages 186-197

Abstract

  The highly substituted pyridine derivatives are found to exhibit diverse pharmacological activities. They are also emerged as potential medicinal leads in developing therapeutic agents for the treatment of various diseases. In this work, a series of 2-amino-3,5-dicarbonitrile-6-thio-pyridine derivatives ...  Read More The highly substituted pyridine derivatives are found to exhibit diverse pharmacological activities. They are also emerged as potential medicinal leads in developing therapeutic agents for the treatment of various diseases. In this work, a series of 2-amino-3,5-dicarbonitrile-6-thio-pyridine derivatives have been synthesized at room temperature via one-pot, multi-component reaction of various aromatic aldehydes, malononitrile and thiophenols using catalytic amount of tetrabutylammonium bromide (TBAB) and cesium carbonate in methanol. In the present method, the use of thermal condition is avoided. In addition, the advantages such as operational simplicity, economic viability, ecologically benign nature make this protocol a very efficient alternative to the literature methods.

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Organic chemistry

Vanadium oxide supported on mesocellulous silica foams (MCF): An efficient and reusable catalyst for selective oxidation of sulfides

Zahra Mohagheghian; Razieh Fazaeli; Hamid Aliyan

Volume 4, Issue 2, pp. 133-235, Serial No. 11 , April 2016, , Pages 198-206

Abstract

  A green, efficient and selective approach for the oxidation of sulfides to sulfoxides and sulfones with UHP at room temperature is reported. The reaction is performed in the presence of vanadia catalyst supported on mesocellular silica foam (MCF) with a V content ranging from 2% to 10% as heterogeneous ...  Read More A green, efficient and selective approach for the oxidation of sulfides to sulfoxides and sulfones with UHP at room temperature is reported. The reaction is performed in the presence of vanadia catalyst supported on mesocellular silica foam (MCF) with a V content ranging from 2% to 10% as heterogeneous and reusable catalyst. The structural and textural characterization of this catalyst were done using FTIR, X-ray diffraction, and N2 adsorption-desorption. This catalyst was found to be effective for selective oxidation of sulfides to sulfoxides and the 5.6% V/MCF catalyst showed the highest activity. It is noteworthy that the reaction tolerates oxidatively sensitive functional groups and the sulfur atom is selectively oxidized.

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Organic chemistry

Sulfamic acid supported on cellulose as a biodegradable and recyclable heterogeneous catalyst for the synthesis of tetrahydrobenzo xanthene derivatives

Batol Zakerinasab; Mohammad Ali Nasseri; Hassan Hassani

Volume 4, Issue 2, pp. 133-235, Serial No. 11 , April 2016, , Pages 214-225

Abstract

  Cellulose bonded N-propyl diethylene tetra sulfamic acid (CBPDETSA) was successfully applied as a green and recyclable acidic catalyst for the synthesis of tetrahydrobenzo [a] xanthene-11-one as an important class of potentially bioactive compounds. The products are obtained by the coupling of 2-naphtol ...  Read More Cellulose bonded N-propyl diethylene tetra sulfamic acid (CBPDETSA) was successfully applied as a green and recyclable acidic catalyst for the synthesis of tetrahydrobenzo [a] xanthene-11-one as an important class of potentially bioactive compounds. The products are obtained by the coupling of 2-naphtol , cyclohexadione and aldehyde derivatives in good to high yields (70- 92%) under solvent-free conditions. The reactivity of different aromatic aldehydes was influenced by the nature and position of the substituents on the aromatic ring. The benzaldehyde derivatives having an electron-withdrawing substituent were highly reactive and gave the products in excellent yields. Also, the catalyst could be recovered by filtration and subjected to a second reaction process. The results show that the yield of product after five runs was only slightly reduced.

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Organic chemistry

One-pot three-component synthesis of dialkyl 3-(alkylamino)-1-aryl-1H-pyrazole-4,5-dicarboxylates using α-Fe2O3 nanoparticles and phenylisocyanate in solvent-free conditions

Bagher Mohammadi; Maryam Rahmani

Volume 4, Issue 2, pp. 133-235, Serial No. 11 , April 2016, , Pages 226-235

Abstract

  This work described a simple and efficient synthesis of dialkyl 3-(alkylamino)-1-aryl-1H-pyrazole-4,5-dicarboxylates via a three component reaction between arylhydrazine, alkylisocyanid and dialkylacetylenedicarboxylates in the presence of phenylisocyanate and α-Fe2O3 nanoparticles. Eco friendly, ...  Read More This work described a simple and efficient synthesis of dialkyl 3-(alkylamino)-1-aryl-1H-pyrazole-4,5-dicarboxylates via a three component reaction between arylhydrazine, alkylisocyanid and dialkylacetylenedicarboxylates in the presence of phenylisocyanate and α-Fe2O3 nanoparticles. Eco friendly, solvent-free conditions, excellent yields, and short reaction times, inexpensive and readily available catalysts are the main advantages of this method. In this work, phenylisocyanate and α-Fe2O3 nanoparticles used as a potent mixed catalyst for promoting the reaction and taking it in a special way to obtain the titled compounds in good to excellent yields. This reaction was not carried out without any of the components of this mixed catalyst. It means that for performance this reaction both of the mixed catalyst components is required.

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Organic chemistry

Solvent-free and one-pot Biginelli synthesis of 3,4-dihydropyrimidin-2(1H)-ones and 3,4-dihydropyrimidin-2(1H)-thiones using ionic liquid N,N-diethyl-N-sulfoethanammonium chloride {[Et3N–SO3H]Cl} as a green catalyst

Saeid Azimi; Marziyeh Hariri

Volume 4, Issue 1, pp. 1-132, Serial No. 10 , January 2016, , Pages 13-20

Abstract

  In this work, the ionic liquid triethylamine-bonded sulfonic acid {[Et3N–SO3H]Cl}, N,N-diethyl-N-sulfoethanammonium chloride was used as a green acidic homogeneous catalyst to synthesis of 3,4-dihydropyrimidin-2(1H)-ones and 3,4-dihydropyrimidin-2(1H)-thiones as two categories of heterocycles, ...  Read More In this work, the ionic liquid triethylamine-bonded sulfonic acid {[Et3N–SO3H]Cl}, N,N-diethyl-N-sulfoethanammonium chloride was used as a green acidic homogeneous catalyst to synthesis of 3,4-dihydropyrimidin-2(1H)-ones and 3,4-dihydropyrimidin-2(1H)-thiones as two categories of heterocycles, from aldehyde, dicarbonyl compound and urea or thiourea throughout the one-pot three components cyclocondensation reactions. The dihidropyrimidineones and dihydropyrimidinethiones derivatives that synthesized in this method are two important categories of heterocyclic compounds with biologic and pharmacologic activity. The ionic liquid that used in these reactions act as Bronsted acid and green homogeneous catalyst and has N-S bond in its cationic fragment and easily synthesised. The advantages of our method are solvent-free conditions, green process and high isolated yield of products.

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Organic chemistry

The three-component reaction of 2-(2-oxopropyl)isoindoline-1,3-dione with alkyl isocyanides and aromatic carboxylic acids under catalyst-free conditions in water

Ali Jafari; Ali Ramazani; Sang Woo Joo; Yavar Ahmadi; Fariba Sadri; Pegah Azimzadeh Asiabi

Volume 4, Issue 1, pp. 1-132, Serial No. 10 , January 2016, , Pages 42-56

Abstract

  A green and convenient protocol is described for the preparation of 1-(alkylamino)-3-(1,3-dioxoisoindolin-2-yl)-2-methyl-1-oxopropan-2-yl benzoates via one-pot three-component reaction between 2-(2-oxopropyl)isoindoline-1,3-dione, an alkyl isocyanide and an aromatic carboxylic acid in water at room temperature. ...  Read More A green and convenient protocol is described for the preparation of 1-(alkylamino)-3-(1,3-dioxoisoindolin-2-yl)-2-methyl-1-oxopropan-2-yl benzoates via one-pot three-component reaction between 2-(2-oxopropyl)isoindoline-1,3-dione, an alkyl isocyanide and an aromatic carboxylic acid in water at room temperature. The methods used to follow the reactions are TLC and NMR, which indicated that there is no side product and the products were obtained without any purification. The structures of the products were deduced from their 1H NMR, 13C NMR and IR spectra. The present methodology offers several advantages such as a simple procedure, catalyst-free, mild reaction conditions, high yields, and the absence of any volatile and hazardous organic solvents.

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Organic chemistry

An efficient one-Pot green synthesis of 4H-Benzo[b]pyrans using guanidinium chloride as polyfunctional organocatalyst

Mahdieh Sadeghpour

Volume 4, Issue 1, pp. 1-132, Serial No. 10 , January 2016, , Pages 57-66

Abstract

  A simple, efficient, and high yielding one-pot protocol has been developed for the synthesis of 4H-benzo[b]pyrans scaffolds installing a three-component tandem Knoevenagel-cyclocondensation reaction of an aldehyde, malononitrile and dimedone using guanidinium chloride as polyfunctional organocatalyst ...  Read More A simple, efficient, and high yielding one-pot protocol has been developed for the synthesis of 4H-benzo[b]pyrans scaffolds installing a three-component tandem Knoevenagel-cyclocondensation reaction of an aldehyde, malononitrile and dimedone using guanidinium chloride as polyfunctional organocatalyst under solvent-free conditions in high to excellent yields. Various aromatic aldehydes were utilized in the reaction and in all situations the desired product were synthesized successfully. The advantageous features of this methodology are operational simplicity, convenient work-up procedures, shorter reaction time and avoiding the use of toxic solvents and purification of products by non-chromatographic methods. The generality and functional tolerance of this convergent and environmentally benign method is demonstrated.

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Organic chemistry

1,3-Disulfonic acid imidazolium hydrogen sulfate {[Dsim]HSO4} as a highly efficient, recyclable and green catalyst for the preparation of α,α´-bis(arylidene)cycloalkanones

Abdolkarim Zare; Mahshad Rezaei; Alireza Hasaninejad

Volume 4, Issue 1, pp. 1-132, Serial No. 10 , January 2016, , Pages 94-101

Abstract

  A highly efficient and simple method for the preparation of α,α´-bis(arylidene)cycloalkanones under solvent-free conditions has been developed. The crossed-aldol condensation of cycloalkanones (1 eq.) with arylaldehydes (2 eq.) in the presence of 2.5 mol% of ionic liquid 1,3-disulfonic ...  Read More A highly efficient and simple method for the preparation of α,α´-bis(arylidene)cycloalkanones under solvent-free conditions has been developed. The crossed-aldol condensation of cycloalkanones (1 eq.) with arylaldehydes (2 eq.) in the presence of 2.5 mol% of ionic liquid 1,3-disulfonic acid imidazolium hydrogen sulfate {[Dsim]HSO4} afforded the title compounds in high yields and short reaction times. The catalyst has dual-functions and it is so because of possessing three acidic functional groups with different Brønsted acidic and basic sites. High catalytic activity and low loading of the catalyst can be attributed to its dual-functions. The promising points for the presented protocol are simple and clean reaction profile, efficiency, generality, low catalyst loading, high yields, performing the reaction in solvent-free media without side reactions, non-toxicity as well as low cost of the catalyst, and good compliance with the green chemistry protocols, which makes it an attractive procedure for the synthesis of α,α´-bis(arylidene)cycloalkanones as an important class of organic compounds.

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Organic chemistry

The anti cancer effects of Stachys Lavandulifolia extract

Mehdi Foruzani; Abbas Ali Dehpour; Mahla Musavi

Volume 3, Issue 4, pp. 283-387, Serial No. 9 , October 2015, , Pages 283-290

Abstract

  Stachys is one of the largest genera in the flowering plant family. It is in the subfamily Lamioideae (Labiatae), spreading and growing in different parts of Iran. The purpose of this study was to investigate the chemical properties of Stachyslavandulifolia as well as the essence, ethanol and methanol ...  Read More Stachys is one of the largest genera in the flowering plant family. It is in the subfamily Lamioideae (Labiatae), spreading and growing in different parts of Iran. The purpose of this study was to investigate the chemical properties of Stachyslavandulifolia as well as the essence, ethanol and methanol extracts of this plant. It was collected from Chulus located in the West of Mazandaran Province. The ethanol and methanol extracts were provided using soxhlet and percolation. The extracts then were defatted and solvent removal performed in a subsequent process. The anticancer activity of extracts was also conducted using MTT assay method in this respect. The test results indicated that there is no significant effect on the inhibition of cell growth when the concentration of extracts is lower than 0.5 mg/ml clarifying that the more the increase in concentration, the more the reduction in growth inhibition.

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Organic chemistry

Three component one-pot synthesis of 4H-benzo-[b]-pyran derivatives using [(diacetoxyiodo)benzene] (DIB) as a hypervalent iodine catalyst

Amit S. Waghmare; Shivaji S. Pandit

Volume 3, Issue 4, pp. 283-387, Serial No. 9 , October 2015, , Pages 291-301

Abstract

  The three components one pot synthesis of 2-amino-4H-benzo-[b] -pyran derivatives were obtained in good to excellent yields within short reaction time by condensing dimedone, aldehydes and malanonitrile or ethylcyanoacetate using a catalytic amount of (diacetoxyiodo)benzene as hypervalent iodine in aqueous ...  Read More The three components one pot synthesis of 2-amino-4H-benzo-[b] -pyran derivatives were obtained in good to excellent yields within short reaction time by condensing dimedone, aldehydes and malanonitrile or ethylcyanoacetate using a catalytic amount of (diacetoxyiodo)benzene as hypervalent iodine in aqueous ethanol under reflux conditions have been discussed. This aqua mediated Knoevenagel-cyclocondensation of various aromatic and hetero-aromatic aldehydes along with the aldehydes like aryl-sulphonyloxybenzaldehyde, aryl-carbonyloxybenzaldehyde also leads to the product under the same reaction conditions. High yields, shorter reaction times, one pot condensation, operational simplicity, easy work-up, purification of products by non-chromatographic methods are some additional features of the present protocol.

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Organic chemistry

Unexpected one pot pseudo four-component reaction for the synthesis of (10E)-N-benzylidene-2-phenylH-imidazo [1,2-a]pyridin-3-amine derivatives under solvent-free conditions

Bagher Mohammadi; Mansoor Shafieey; Hamed Kazemi

Volume 3, Issue 4, pp. 283-387, Serial No. 9 , October 2015, , Pages 302-309

Abstract

  This work described an efficient Pseudo four-component synthesis of (10E)-N-benzylidene-2-phenylH-imidazo[1,2-a]pyridin-3-amine derivatives from 2-aminopyridin, malononitrile and arylaldehydes in the presence of NaOH under solvent-free and conventional heating condition in good to excellent yields. A ...  Read More This work described an efficient Pseudo four-component synthesis of (10E)-N-benzylidene-2-phenylH-imidazo[1,2-a]pyridin-3-amine derivatives from 2-aminopyridin, malononitrile and arylaldehydes in the presence of NaOH under solvent-free and conventional heating condition in good to excellent yields. A wide range of aromatic aldehydes would easily undergo condensations with 2-aminopyridin and malononitrile under solvent-free conditions in order to afford the desired products of good purity in excellent yields. For optimization of this reaction, the effect of NaOH amounts and use of other bases such as Et3N and Na2CO3 instead of NaOH and the efficacy of time and temperature to the reaction yields were studied. The use of simple and readily available starting materials, pharmacologically interest product, short reaction times, and applications in bioorganic and medicinal chemistry are the main advantages of this reaction.

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Organic chemistry

Preparation of sterically congested 1,3,4-oxadiazole derivatives from N-isocyaniminotriphenylphosphorane, aromatic acids, cyclopentanone and primary amines

Hamideh Javanbani; Ali Ramazani; Sang Woo Joo; Yavar Ahmadi; Vahid Azizkhani; Pegah Azimzadeh Asiabi

Volume 3, Issue 4, pp. 283-387, Serial No. 9 , October 2015, , Pages 310-322

Abstract

  Reactions of N-isocyaniminotriphenylphosphorane with cyclopentanone have been studied in the presence of aromatic carboxylic acids and primary amines, proceeds smoothly at room temperature under neutral conditions to afford sterically congested 1,3,4-oxadiazole derivatives by an intramolecular Aza-Wittig ...  Read More Reactions of N-isocyaniminotriphenylphosphorane with cyclopentanone have been studied in the presence of aromatic carboxylic acids and primary amines, proceeds smoothly at room temperature under neutral conditions to afford sterically congested 1,3,4-oxadiazole derivatives by an intramolecular Aza-Wittig cyclization in CH2Cl2 in excellent yields. The structures of the products were deduced from their IR, Mass, ¹H NMR, and ¹³C NMR spectra. The reaction proceeds smoothly and cleanly under mild conditions and no side reactions were observed. The method offers a mild, simple, and efficient route for the preparation of fully substituted 1,3,4-oxadiazoles from cyclopentanone, primary amines, N-isocyaniminotriphenylphosphorane and aromatic carboxylic acids. Easy work-up, high yields and fairly mild reaction conditions make it a useful procedure in comparison to the modern synthetic methodologies.

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Organic chemistry

Synthesis of some network polymers with siloxane units as a drug delivery system

Mohammad Galehassadi; Samad Omidi

Volume 3, Issue 4, pp. 283-387, Serial No. 9 , October 2015, , Pages 323-334

Abstract

  New biodegradable network polymers containing siloxane-linked polymeric prodrugs of 5-ammino-2-hydroxybenzoic acid (5-ASA) in the main chain were prepared by ter polymerization of methacrylic acid (MA), 2-hydroxyethylmethacrylate (HEMA), and bis (trimethylsilyloxy) methylsilane (VBM) in the presence ...  Read More New biodegradable network polymers containing siloxane-linked polymeric prodrugs of 5-ammino-2-hydroxybenzoic acid (5-ASA) in the main chain were prepared by ter polymerization of methacrylic acid (MA), 2-hydroxyethylmethacrylate (HEMA), and bis (trimethylsilyloxy) methylsilane (VBM) in the presence of some new cross-linking agents.The monomers and polymers were characterized by FT-IR and 1H-NMR spectroscopy, and their thermal stability studied by DSC analysis. The hydrolysis of them were carried out in cellophane membrane dialysis bags containing aqueous buffer solution at 37 C. Detection of the hydrolysis product by UV spectroscopy method showed that attaching of siloxane units in these hydrogels modified this drug delivery system.

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Organic chemistry

Efficient procedure for the synthesis of quinoline derivatives by NbCl5.PEG and NbCl5 in glycerol as green solvent

Batol Zakerinasab; Mohammad Ali Nasseri; Fateme Kamali

Volume 3, Issue 4, pp. 283-387, Serial No. 9 , October 2015, , Pages 335-347

Abstract

  Quinolines, an important class of potentially bioactive compounds, have been synthesized by treatment of O-aminoarylketones and carbonyl compounds utilizing niobium (V) chloride / polyethylenglycole(NbCl5.PEG) and niobium(V)chloride (NbCl5) as available and inexpensive catalysts. The quinoline derivatives ...  Read More Quinolines, an important class of potentially bioactive compounds, have been synthesized by treatment of O-aminoarylketones and carbonyl compounds utilizing niobium (V) chloride / polyethylenglycole(NbCl5.PEG) and niobium(V)chloride (NbCl5) as available and inexpensive catalysts. The quinoline derivatives were prepared in glycerol, an excellent solvent in terms of environmental impact, with high yields (76-98%) and short reaction times (15- 90 min). Not only diketones but also ketones afforded the desired products in good to excellent yields. The reaction time of 2-amino-5-chlorobenzophenone and dicarbonyl compounds was longer than those of 2-aminobenzophenone. The reaction of cyclic diketones took place faster than open chain analogues. These reactions also proceeded with acetophenone derivatives. In these cases the reaction times are longer.

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Organic chemistry

[BMIm]BF4-LiCl as an effective catalytic system for the synthesis of dicoumarols

Seyyedeh Cobra Azimi; Kurosh Rad-Moghadam

Volume 3, Issue 4, pp. 283-387, Serial No. 9 , October 2015, , Pages 356-366

Abstract

  A homogeneous ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate doped with LiCl ([BMIm]BF4-LiCl) was found as catalyst solvents for the synthesis of dicoumarols by the condensation of 4-hydroxycoumarin and aldehyde at 80 ˚C. In this field, several types of aromatic aldehyde, containing electron-withdrawing ...  Read More A homogeneous ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate doped with LiCl ([BMIm]BF4-LiCl) was found as catalyst solvents for the synthesis of dicoumarols by the condensation of 4-hydroxycoumarin and aldehyde at 80 ˚C. In this field, several types of aromatic aldehyde, containing electron-withdrawing groups as well as electron-donating groups, were rapidly changed to the corresponding derivatives in good to excellent yields. Application of this new homogeneous catalyst system offered the advantages of short reaction times, solvent-free conditions, high yields, and easy work-up procedure compared to the conventional methods of the syntheses. The ionic liquid can be recovered for the subsequent reactions and reused without any loss of efficiency.

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Organic chemistry

Green and efficient synthesis of trialkyl (E)-3-(3-Oxo-2-3,4-dihydro-2-(1H)-quinoxalinylidene)-prop-1-ene-1,2,3- tricarboxylates using K2CO3-PEG-400 as robust catalytic system

Mohammad Piltan

Volume 3, Issue 4, pp. 283-387, Serial No. 9 , October 2015, , Pages 367-373

Abstract

  An efficient synthesis of trialkyl (E)-3-(3-Oxo-2-3,4-dihydro-2-(1H)-quinoxalinylidene)-prop-1-ene-1,2,3-tricarboxylate derivatives via a simple three-component reaction between benzene-1,2-diamines with dialkyl acetylenedicarboxylates in the presence of K2CO3-PEG catalytic system at 100 oC was reported. ...  Read More An efficient synthesis of trialkyl (E)-3-(3-Oxo-2-3,4-dihydro-2-(1H)-quinoxalinylidene)-prop-1-ene-1,2,3-tricarboxylate derivatives via a simple three-component reaction between benzene-1,2-diamines with dialkyl acetylenedicarboxylates in the presence of K2CO3-PEG catalytic system at 100 oC was reported. The desired products were obtained in excellent yields (88-92%). Various benzene-1,2-diamines, and dialkyl acetylendicarboxylate were used in the traditional method. Quinolines are major classes of heterocyclic compounds, which have attracted considerable attention from chemists for their large broad biological activities and amazing physical properties. Furthermore, the synthesis of quinoxalines and their derivatives has received much attention from organic and medicinal chemists. As part of our current studies on the development of new routes to synthesize quinoxaline systems. The corresponding quinoxalines are useful building blocks for the construction of complex quinoxaline derivatives

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Organic chemistry

A comparative study of catalytic properties of ZnO and FeZnO nanoparticles on Oxidation of Benzylic alcohols: Influence of doped metal

Hamid Reza Mardani Kiasari; Mehdi Forouzani; Mitra Ziari; Azim Malekzadeh; Pouria Biparva

Volume 3, Issue 3, pp. 180-282,Serial No. 8 , July 2015, , Pages 199-207

Abstract

  Novel nano-catalysts (Nano ZnO and Fe doped ZnO (Fe(0.1)Zn(0.99)O) synthesized by co-precipitation method in aqueous solution as new nanocatalysts and characterized by common techniques as FTIR, XRD, SEM and UVD. The size of particles obtained from XRD data is 27 and 16 nanometers for ZnO and Fresno ...  Read More Novel nano-catalysts (Nano ZnO and Fe doped ZnO (Fe(0.1)Zn(0.99)O) synthesized by co-precipitation method in aqueous solution as new nanocatalysts and characterized by common techniques as FTIR, XRD, SEM and UVD. The size of particles obtained from XRD data is 27 and 16 nanometers for ZnO and Fresno respectively. Influences of doped Fe on ZnO catalytic properties in oxidation of Benzylic alcohols were studied. The oxidation carried out under mild and green conditions as: solvent free, at room temperature and with H2O2. The results show, FeZnO is better than ZnO as nanocatalyst in oxidation reaction. The rate, %conversion and %selectivity of reaction are improved in the presence of Fe atoms than ZnO only. The main product of oxidation reactions is Benzaldehyde and/or its derivatives.

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Organic chemistry

Melamine trisulfonic acid as a highly efficient catalyst for the synthesis of polyhydroquinolines under solvent-free conditions

Abdolkarim Zare; Maryam Dashtizadeh; Maria Merajoddin

Volume 3, Issue 3, pp. 180-282,Serial No. 8 , July 2015, , Pages 208-217

Abstract

  A highly efficient, simple and clean solvent-free protocol for the synthesis of polyhydroquinolines is described. The one-pot multi-component condensation reaction between arylaldehydes, dimedone (5,5-dimethylcyclohexane-1,3-dione), β-ketoesters and ammonium acetate in the presence of catalytic ...  Read More A highly efficient, simple and clean solvent-free protocol for the synthesis of polyhydroquinolines is described. The one-pot multi-component condensation reaction between arylaldehydes, dimedone (5,5-dimethylcyclohexane-1,3-dione), β-ketoesters and ammonium acetate in the presence of catalytic amount of (2.5 mol%) melamine trisulfonic acid (MTSA) as a recyclable, green and attractive sulfonic acid-containing catalyst at 60 °C affords the title compounds in high yields (83-98%) and short reaction times (3-30 min). The advantages of this method are efficiency, generality, high yield, short reaction time, cleaner reaction profile, simplicity, recyclability of the catalyst, ease of product isolation, and good compliance with the green chemistry protocols.

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Organic chemistry

The green synthesis of pyrano[3,2-c]quinoline-2,5-dione derivatives catalyzed by acidic ionic liquid under ultrasound irradiation

Esmayeel Abbaspour-Gilandeh; Seyyedeh Cobra Azimi

Volume 3, Issue 3, pp. 180-282,Serial No. 8 , July 2015, , Pages 218-231

Abstract

  Abstract-A novel and efficient method has been developed for the synthesis of pyrano[3,2-c]quinoline-2,5-dione derivatives by the convenient ultrasound-mediated condensation of 4-hydroxyquinolin-2-one with Meldrum’s acid and aldehydes in the presence of a catalytic amount of [HMIm]HSO4 as a green, ...  Read More Abstract-A novel and efficient method has been developed for the synthesis of pyrano[3,2-c]quinoline-2,5-dione derivatives by the convenient ultrasound-mediated condensation of 4-hydroxyquinolin-2-one with Meldrum’s acid and aldehydes in the presence of a catalytic amount of [HMIm]HSO4 as a green, efficient and reusable acidic ionic liquid medium. The stability of the ionic liquid during the reaction was high and, used for several times to recycled form. Placing the reaction mixture under ultrasound condition causes that we have lower energy consumption and achieve to the desired product in the optimal time. The method is simple, starts from readily accessible commercial starting materials, and provides biologically interesting products in good yields and short reaction times.

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Organic chemistry

One-pot reductive Amination of Carbonyl Compounds using NaBH4 and Fe3O4 Magnetic Nanoparticles

Mehdi Forouzani; Navabeh Nami; Hassan Ghasemnejad-Bosra; Omid Khalilpour Tylami

Volume 3, Issue 3, pp. 180-282,Serial No. 8 , July 2015, , Pages 232-243

Abstract

  One-pot reaction of aldehydes or ketons with aniline derivatives was performed using NaBH4 and Fe3O4 magnetic nanoparticles (MNPs). The optimum amount of Fe3O4 MNPs was 5 mol% under solvent free condition. The corresponding products were obtained in good to excellent yields. The magnetically recoverable ...  Read More One-pot reaction of aldehydes or ketons with aniline derivatives was performed using NaBH4 and Fe3O4 magnetic nanoparticles (MNPs). The optimum amount of Fe3O4 MNPs was 5 mol% under solvent free condition. The corresponding products were obtained in good to excellent yields. The magnetically recoverable iron oxide nanoparticles are found to be efficient for synthesis of amine derivatives. These nanoparticles are effective in green chemistry and could be successfully reuse. in addition to having the general advantages attributed to the inherent magnetic property of nanocatalyst, Fe3O4MNPs exhibited exceptionally high catalytic activity compared to other catalysts, to yield the desired products in short reaction time and mild reaction conditions.

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