Iranian chemical communication

Organic chemistry

N,N,N,N-Tetramethylguanidinium acetate as an efficient and reusable ionic liquid catalyst for the one-pot synthesis of dihydropyrrol-2-ones

Seyed Sajad Sajadikhah

Volume 5, Issue 2, pp. 121-236, Serial No. 15 , April 2017, , Pages 121-128

Abstract

  An extremely facile and efficient procedure which has been developed for the synthesis of dihydropyrrol-2-ones. One-pot four-component reaction of amines, dialkyl acetylenedicarboxylates and formaldehyde in the presence of N,N,N,N-tetramethylguanidinium acetate [TMG][Ac] in methanol at ambient temperature ...  Read More An extremely facile and efficient procedure which has been developed for the synthesis of dihydropyrrol-2-ones. One-pot four-component reaction of amines, dialkyl acetylenedicarboxylates and formaldehyde in the presence of N,N,N,N-tetramethylguanidinium acetate [TMG][Ac] in methanol at ambient temperature provides substituted dihydropyrrol-2-ones in good to high yields. The important aspects of this multi-component heteroannulation are simple operations under mild conditions, readily available starting material and catalyst. Furthermore, All products were obtained through a simple filtration and washed with ethanol and no need for column chromatography. It is found that the catalyst is recyclable and can be used up to four times without significant loss of its activity.

---

• View Article
• PDF 663.39 K

Organic chemistry

Magnetic nanoparticle immobilized N-propylsulfamic acid: The efficient, green and reusable nanocatalyst for the synthesis of substituted coumarins

Hassan Ghasemnejad-Bosra; Amin Rostami

Volume 5, Issue 2, pp. 121-236, Serial No. 15 , April 2017, , Pages 129-137

Abstract

  N-Propylsulfamic acid supported onto magnetic Fe3O4 nanoparticles (MNPs-PSA) was investigated as an efficient and magnetically recoverable catalyst for the one-pot synthesis of substituted coumarins from the reaction of coumarin with variety aromatic aldehydes in high to excellent yield at room temperature ...  Read More N-Propylsulfamic acid supported onto magnetic Fe3O4 nanoparticles (MNPs-PSA) was investigated as an efficient and magnetically recoverable catalyst for the one-pot synthesis of substituted coumarins from the reaction of coumarin with variety aromatic aldehydes in high to excellent yield at room temperature under solvent-free conditions. The magnetic nanocatalyst can be readily recovered easily by applying an external magnet device and reused for at least 10 reaction runs without considerable loss of reactivity. The advantages of this protocol are the use of a commercially available, eco-friendly, cheap, the mild reaction conditions, operational simplicity, practicability, short reaction times, and good to high yields

---

• View Article
• PDF 733.98 K

Organic chemistry

A Facile and environmental friendly method for C=N bond cleavage of imines using p-toluenesulfonic acid in solid State

Gholamhassan Imanzadeh; Hamideh Vakili

Volume 5, Issue 2, pp. 121-236, Serial No. 15 , April 2017, , Pages 147-155

Abstract

  A simple, efficient and clean procedure has been developed for the cleavage of imines C=N bond. Deprotection of imines to their parent carbonyl and amine compounds was achieved using p-toluenesulfonic acid in the solid state condition at 25-45 ˚C. The salient features of this methodology are shorter ...  Read More A simple, efficient and clean procedure has been developed for the cleavage of imines C=N bond. Deprotection of imines to their parent carbonyl and amine compounds was achieved using p-toluenesulfonic acid in the solid state condition at 25-45 ˚C. The salient features of this methodology are shorter reaction times, cheap processing, high yields of product and easy availability of the catalyst. These features make this method an attractive alternative to existing routes for deprotection of iminesA simple, efficient and clean procedure has been developed for the cleavage of imines C=N bond. Deprotection of imines to their parent carbonyl and amine compounds was achieved using p-toluenesulfonic acid in the solid state condition at 25-45 ˚C. The salient features of this methodology are shorter reaction times, cheap processing, high yields of product and easy availability of the catalyst. These features make this method an attractive alternative to existing routes for deprotection of imines

---

• View Article
• PDF 786.2 K

Organic chemistry

A clean and highly efficient synthesis of oxindole substituted pyrrolo[2,3-d]Pyrimidines under ultrasound irradiation

Seyyedeh Cobra Azimi; Kurosh Rad-Moghadam

Volume 5, Issue 2, pp. 121-236, Serial No. 15 , April 2017, , Pages 156-166

Abstract

  A practical and new method for the synthesis oxindole substituted pyrrolo[2,3-d]pyrimidines by the condensation of isatin, acetophenone and 6-amino-uracil under ultrasound irradiation conditions at 60 °C was described. The reaction was developed via a sequential tandem process to afford the oxindole ...  Read More A practical and new method for the synthesis oxindole substituted pyrrolo[2,3-d]pyrimidines by the condensation of isatin, acetophenone and 6-amino-uracil under ultrasound irradiation conditions at 60 °C was described. The reaction was developed via a sequential tandem process to afford the oxindole substituted pyrrolo[2,3-d]pyrimidines in good to excellent yields. All reactions performed efficiently under ultrasound irradiation and results were compared with conventional heating method. In this field, several types of acetophenones, amino-uracils, and isatins were rapidly changed to the corresponding derivatives. The remarkable features of the new procedure are shorter reaction time, excellent yields, cleaner reaction profile, and simple experimental and workup procedure.

---

• View Article
• PDF 726.11 K

Organic chemistry

Highly efficient synthesis of tetrahydrobenzo[b]pyrans under visible light promoted by cesium carbonate

Vinod Kamble; Munazza Sadaf; Bushra Saleh

Volume 5, Issue 2, pp. 121-236, Serial No. 15 , April 2017, , Pages 167-172

Abstract

  Multi-component coupling reaction (MCR) is a powerful synthetic tool for the synthesis of biologically active compounds. Development of such multi-component coupling reaction strategies in visible light has been of considerable interest, as they provide simple and rapid access to a large number of organic ...  Read More Multi-component coupling reaction (MCR) is a powerful synthetic tool for the synthesis of biologically active compounds. Development of such multi-component coupling reaction strategies in visible light has been of considerable interest, as they provide simple and rapid access to a large number of organic molecules through a sustainable path. An efficient and green protocol for the synthesis of tetrahydrobenzo[b]pyrans derivatives by one-pot, three component coupling reaction of aromatic aldehyde, malononitrile, and dimedone has been developed using readily available cesium carbonate as the catalyst under visible light. This efficient procedure has the advantages of giving the target compounds in high yields, short reaction times, simple work-up procedure, use of chief and easily available catalyst, and environmentally benign conditions.

---

• View Article
• PDF 563.18 K

Organic chemistry

New 16-membered macrocyclic Schiff base: Synthesis, structural and FT-IR studies

Aliakbar Dehno Khalaji; Salar Hafez Goran; Sepideh Mehrani; Karla Fejfarova; Michal Dusek

Volume 5, Issue 2, pp. 121-236, Serial No. 15 , April 2017, , Pages 186-194

Abstract

  In this paper, the structure of a new 16-membered macrocyclic Schiff base compound N,N′-(3,3′-dimethoxy-2,2′-(propane-1,3-diyldioxy)dibenzylidene)propane-1,3-diamine, C22H26N2O4 (1), derived from 1,3-propanediamine and 3,3′-dimethoxy-2,2′-(propane-1,3-diyldioxy)dibenzaldehyde ...  Read More In this paper, the structure of a new 16-membered macrocyclic Schiff base compound N,N′-(3,3′-dimethoxy-2,2′-(propane-1,3-diyldioxy)dibenzylidene)propane-1,3-diamine, C22H26N2O4 (1), derived from 1,3-propanediamine and 3,3′-dimethoxy-2,2′-(propane-1,3-diyldioxy)dibenzaldehyde has been studied by single crystal X-ray diffraction, DFT calculations at B3LYP/6-31G** and FT-IR spectroscopy. The title compound crystallizes in the monoclinic space group P21/n with unit cell parameters: a = 16.3273 (5) Å, b = 7.0832 (2) Å, c = 16.8586 (4) Ǻ, β = 93.135 (2)°, V = 1946.77 (9) Å3 and Z=4. The optimized molecular geometry agrees closely to that obtained from single crystal X-ray crystallography. The FT-IR spectrum (4000-400 cm-1) was recorded and compared with that of the calculated spectrum.

---

• View Article
• PDF 841.72 K

Organic chemistry

Design, synthesis and anticancer evaluation of novel thiazine, pyrimidine and pyridine derivatives

Amira A. Ghoneim; Mohamed G. Assy; Enaiat K. Mohamed; Islam Ragab

Volume 5, Issue 2, pp. 121-236, Serial No. 15 , April 2017, , Pages 195-206

Abstract

  Acylisothiocyanate (1) was allowed to react with benzylidene malononitrile producing oxazine derivative (2). Also, compound (1) was reacted with sodium azide followed by refluxing with sodium ethoxide affording thiazinotetrazole derivative (4). The reaction of acetylacetone with compound (1) gave pyridine ...  Read More Acylisothiocyanate (1) was allowed to react with benzylidene malononitrile producing oxazine derivative (2). Also, compound (1) was reacted with sodium azide followed by refluxing with sodium ethoxide affording thiazinotetrazole derivative (4). The reaction of acetylacetone with compound (1) gave pyridine derivative (5) by intramolecular cycloaddition while it was reacted with N-methyl aniline affording thiazine derivative (7). In addition, it was reacted with cyanoacetamide producing mercaptopyrimidine derivative (9). Finally, compound (1) was refluxed with phenylhydrazine, urea, guanidinum carbonate and anthranilic acid in the presence of dry acetone affording triazole derivative (11), N-substituted pyrimidine (15), compound (18) and thiopyrimidine derivative (19) respectively. The structures of the new compounds were confirmed on the basis of elemental and spectral data. Some of the synthesized compounds were screened as anticancer.

---

• View Article
• PDF 839.13 K

Organic chemistry

Electron as potential and green catalyst in the multicomponent synthesis of pyrano [2, 3-d] pyrimidine derivatives

Hojat Veisi; Abbas Maleki; Yasaman Farokhzad

Volume 5, Issue 2, pp. 121-236, Serial No. 15 , April 2017, , Pages 217-226

Abstract

  An electroorganic reaction for the synthesis of 7-amino-2, 4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-pyrano[2, 3-d] pyrimidine-6-carbonitrile and ethyl-7-amino-2, 4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-pyrano[2, 3-d] pyrimidine-6-carboxylate derivatives are described, using an electrogenerated base of the ...  Read More An electroorganic reaction for the synthesis of 7-amino-2, 4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-pyrano[2, 3-d] pyrimidine-6-carbonitrile and ethyl-7-amino-2, 4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-pyrano[2, 3-d] pyrimidine-6-carboxylate derivatives are described, using an electrogenerated base of the anion of malonitrile or ethylcyanoacetate. This one-pot, three-component condensation of an aromatic aldehyde, barbituric acid and malonitrile or ethylcyanoacetate takes place in ethanol in an undivided cell in the presence of tetrabutylammonium perchlorate as an electrolyte under mild conditions. This method has the advantages of high yields, wide application and employs an environmentally benign procedure.An electroorganic reaction for the synthesis of 7-amino-2, 4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-pyrano[2, 3-d] pyrimidine-6-carbonitrile and ethyl-7-amino-2, 4-dioxo-5-phenyl-2,3,4,5-tetrahydro-1H-pyrano[2, 3-d] pyrimidine-6-carboxylate derivatives are described, using an electrogenerated base of the anion of malonitrile or ethylcyanoacetate. This one-pot, three-component condensation of an aromatic aldehyde, barbituric acid and malonitrile or ethylcyanoacetate takes place in ethanol in an undivided cell in the presence of tetrabutylammonium perchlorate as an electrolyte under mild conditions. This method has the advantages of high yields, wide application and employs an environmentally benign procedure.

---

• View Article
• PDF 674.5 K

Organic chemistry

Guanidine hydrochloride: An efficient catalyst for the synthesis of 2-hydrazolyl-4-thiazolidinone derivatives under solvent free conditions

Shivaji Sandu Pandit; Sonali Shivaji Pardhe; Yashwant Bhaskar Pandit

Volume 5, Issue 2, pp. 121-236, Serial No. 15 , April 2017, , Pages 227-236

Abstract

  A Highly efficient protocol has been developed for the synthesis of 2-hydrazolyl-4-thiazolidinone derivatives installing a one pot three component coupling reaction of an aromatic aldehyde, thiosemicarbazide and maleic anhydride using guanidine hydrochloride as highly inexpensive and environmentally ...  Read More A Highly efficient protocol has been developed for the synthesis of 2-hydrazolyl-4-thiazolidinone derivatives installing a one pot three component coupling reaction of an aromatic aldehyde, thiosemicarbazide and maleic anhydride using guanidine hydrochloride as highly inexpensive and environmentally friendly catalyst under solvent free condition at 1200C with good to excellent yields, It offers short reaction time, good to excellent yields and simple and easy workup procedure as compared to the traditional methods of synthesis. The products are characterized by spectroscopic methods like IR and 1H NMR. In the present protocol we reports unsaturated aldehydes first time using guanidine hydrochlori with excellent yields.

---

• View Article
• PDF 734.23 K

Organic chemistry

Synthesis and characterization of new (2E,2'E)-3,3'-(((3-hydroxypropane-1,2-diyl)bis(oxy))bis (2,1-phenylene))bis(1-phenylprop-2-en-1-one) and its transformation into 2,3-bis(2-(1,3-diphenyl-4,5-dihydro-1H-pyrazol-5-yl)phenoxy)propan-1-ol

Alireza Banaei; Soheyla Karimi; Somayeh Minaei; Eslam Pourbasheer

Volume 5, Issue 1, pp. 1-120, Serial No. 14 , January 2017, , Pages 1-6

Abstract

  In this paper, new (2E, 2'E)-3, 3'-(((3- hydroxypropane-1, 2-diyl) bis (oxy)) bis (2, 1-phenylene)) bis (1-phenylprop-2-en-1-one) (2a) was prepared in good yield by condensation reaction of acetophenone with bisaldehyde (1a) in ethanolic NaOH solutions at room temperature. The (2E, 2'E)-3, 3'-(((3- hydroxypropane-1, ...  Read More In this paper, new (2E, 2'E)-3, 3'-(((3- hydroxypropane-1, 2-diyl) bis (oxy)) bis (2, 1-phenylene)) bis (1-phenylprop-2-en-1-one) (2a) was prepared in good yield by condensation reaction of acetophenone with bisaldehyde (1a) in ethanolic NaOH solutions at room temperature. The (2E, 2'E)-3, 3'-(((3- hydroxypropane-1, 2-diyl) bis (oxy)) bis (2, 1-phenylene)) bis (1-phenylprop-2-en-1-one) (2a) was immediately reacted with phenyl hydrazine under refluxing conditions in the presence of potassium hydroxide to obtain the corresponding 2, 3-bis (2-(1, 3-diphenyl-4, 5-dihydro-1H-pyrazol-5-yl) phenoxy) propan-1-ol (3a). The newly synthesized compounds confirmed by melting point and TLC and their structure were established by various analytical techniques such as IR, 1H-NMR, 13C-NMR and elemental analysis.

---

• View Article
• PDF 351.91 K

Organic chemistry

One-pot synthesis of 2-oxo-1,2,3,4-tetrahydropyrimidines using homogeneous catalyst under solvent-free conditions

Asadollah Farhadi; Mohammad Ali Takassi; Lila Hejazi

Volume 5, Issue 1, pp. 1-120, Serial No. 14 , January 2017, , Pages 35-41

Abstract

  The chemistry of 2-oxo-1,2,3,4-tetrahydropyrimidines began to develop toward the end of 1893 year, when the first representatives of this class compounds were reported by P. Biginelli. Despite prior reports of several really effective catalytic and non-catalytic approaches towards Biginelli-type products, ...  Read More The chemistry of 2-oxo-1,2,3,4-tetrahydropyrimidines began to develop toward the end of 1893 year, when the first representatives of this class compounds were reported by P. Biginelli. Despite prior reports of several really effective catalytic and non-catalytic approaches towards Biginelli-type products, an overwhelming number of new catalysts for the Biginelli reaction have been recently published. Most of the catalysts are somewhat exotic, expensive, harmful and even ineffective in the absence of acidic additives. This work reports on the preparation of 2-oxo-1,2,3,4-tetrahydropyrimidines using the NaF as catalyst. One-pot condensation reactions were carried out for various aryl aldehydes, ethyl acetoacetate, acetyl acetone and urea under solvent-free conditions at 100 °C and afforded the target molecules in good to excellent yields. The advantages of this method are high yield of product, short reaction time, and separation of this catalyst is very comfortable. Furthermore, according to the experimental data, we have proposed the suitable mechanism.

---

• View Article
• PDF 106.7 K

Organic chemistry

Isoquinoline promoted Synthesis of alkyl 2-(1-alkyl-5-oxo-3-phenyl-2-thioxotetrahydro-4H-imidazol-4-yliden) acetate derivatives

Rahimeh Hajinasiri; Sanaz Baravardeh; Sobhan Rezayati

Volume 5, Issue 1, pp. 1-120, Serial No. 14 , January 2017, , Pages 52-57

Abstract

  Derivatives of thiazolidinone ring systems are known to act as anti-HIV infections , analgesic, anti-bacterial, anti-convulsant, anti parasitic, potential anti-inflammatory and herbicidal agents. Due biological activities of thiazolidinones ring, several methods for their synthesis have been illustrated ...  Read More Derivatives of thiazolidinone ring systems are known to act as anti-HIV infections , analgesic, anti-bacterial, anti-convulsant, anti parasitic, potential anti-inflammatory and herbicidal agents. Due biological activities of thiazolidinones ring, several methods for their synthesis have been illustrated in literature. Imidazolidine-2-thiones were synthesized by the oxidative cyclization of 1-benzoyl-3-aryl-thioureas with bromine and enolizable carbonyl compounds in the presence of excess triethylamine . A suitable method for the synthesis of fused thiazoles were described from the reaction of aroylphenyl thioureas with π-acceptor quinones. An efficient and one-pot method for the synthesis alkyl 2-(1-alkyl-5-oxo-3-phenyl-2-thioxotetrahydro-4H-imidazol-4-yliden) acetate derivatives via simple reaction between isoquinoline, dialkyl acetylenedicarboxylate and benzyl phenylthiourea under solvent-free conditions without using any additional catalyst, is described. The mild reaction conditions and good yields and exhibit the synthetic advantage of this method. Also this method is environmentally friendly.

---

• View Article
• PDF 113.64 K

Organic chemistry

Highly efficient and rapid synthesis of diverse hydantoin derivatives using nano-ordered ZnO catalyst under mechanochemical ball milling

Bozorg Maddah

Volume 5, Issue 1, pp. 1-120, Serial No. 14 , January 2017, , Pages 58-66

Abstract

  A mild and efficient one-pot three-component and environmentally benign approach for the synthesis of a wide range of hydantoin annulated derivatives has been described. A multi-component reaction between a carbonyl compounds (ketone or aldehyde), potassium cyanide and ammonium carbonate (as cyanating ...  Read More A mild and efficient one-pot three-component and environmentally benign approach for the synthesis of a wide range of hydantoin annulated derivatives has been described. A multi-component reaction between a carbonyl compounds (ketone or aldehyde), potassium cyanide and ammonium carbonate (as cyanating agent and amine source, respectively leads to the formation of hydantoins. The proposed optimized reaction conditions ,i.e. solvent-free conditions under ambient temperature in the presence of low amount of ZnOnano-catalyst, were very efficient resulting in the formation of the desired products with good to excellent yields. Furthermore, the presented methodology is in accord with green chemistry principles.Keywords: Bucherer-Bergs; hydantoin derivatives; multicomponent reactions (MCRs); green chemistry.

---

• View Article
• PDF 1011.56 K

Organic chemistry

Liquid phase bromination of phenols over silicotungstic acid immobilized on nickel oxide nanoparticles

Abbas Mirzaie; Ahmad Afzalinia; Tahereh Musabeygi

Volume 5, Issue 1, pp. 1-120, Serial No. 14 , January 2017, , Pages 99-104

Abstract

  Heteropoly acid promoted nanoparticle of nickel oxide samples were prepared by sol-gel method using heteropoly acids. Prepared composite was characterized by XRD, FT-IR and ICP technique. In this work, we have reported bromination of phenol, its derivatives and some aromatic compounds. The liquid phase ...  Read More Heteropoly acid promoted nanoparticle of nickel oxide samples were prepared by sol-gel method using heteropoly acids. Prepared composite was characterized by XRD, FT-IR and ICP technique. In this work, we have reported bromination of phenol, its derivatives and some aromatic compounds. The liquid phase bromination of phenol was Performed using heteropoly acids immobilized nanoparticle of nickel oxide as catalyst, KBr as brominating agent and hydrogen peroxide as an oxidant in acetonitrile at room temperature. The reaction proceeds through the formation of Br+ (bromonium ion), which attacks the phenol ring forming different brominated products. Prepared catalyst can be used several times without a significant decline in catalytic activity.

---

• View Article
• PDF 127.97 K

Organic chemistry

Indium chloride (InCl3) catalysed domino protocol for the regioselective synthesis of highly functionalized pyranopyrazoles under mild conditions

Hemant Chavan; Datta Survase; Sakharam Dongare; Vasant Helavi; Shreeram Ganapure

Volume 5, Issue 1, pp. 1-120, Serial No. 14 , January 2017, , Pages 105-114

Abstract

  Regioselective synthesis of highly functionalized pyranopyrazoles was achieved in excellent yield from phenyl pyrazolone, substituted aromatic aldehyde with nitroketene-N,S-acetal in the presence of indium trichloride as a versatile catalyst under reflux condition in ethanol-water mixture. All reactions ...  Read More Regioselective synthesis of highly functionalized pyranopyrazoles was achieved in excellent yield from phenyl pyrazolone, substituted aromatic aldehyde with nitroketene-N,S-acetal in the presence of indium trichloride as a versatile catalyst under reflux condition in ethanol-water mixture. All reactions preceeded within a short period of time with excellent purity. All of the synthesized compounds were identified by IR, 1H NMR, 13C NMR and mass spectroscopy. Quantitative yields, inexpensive and environmentally friendly solvent system and simple work-up procedure are the attractive features of the present method. It is thus enviro-economic method without producing hazardous wastes. The formed pyranopyrazoles might find to possess important biological and pharmaceutical applications.

---

• View Article
• PDF 463.66 K

Organic chemistry

Tetra-N-Butyl ammonium hydroxide mediated one-pot synthesis of pyrano [2, 3-d] pyrimidinone derivatives

Vivekanand Jadhav; Mohasim M. Patel

Volume 5, Issue 1, pp. 1-120, Serial No. 14 , January 2017, , Pages 115-120

Abstract

  Tetra-N-Butyl Ammonium Hydroxide was used as a catalyst for one-pot, three component condensation reactions consisting of aromatic aldehydes, malononitrile and barbituric acid in ethanol:water solvent system at 60oC. Current method has major advantages like mild reaction conditions with simple operation, ...  Read More Tetra-N-Butyl Ammonium Hydroxide was used as a catalyst for one-pot, three component condensation reactions consisting of aromatic aldehydes, malononitrile and barbituric acid in ethanol:water solvent system at 60oC. Current method has major advantages like mild reaction conditions with simple operation, high yields, by using a less toxic and lower costlier catalyst.In conclusion, we have explored nicely the synthetic utility of TBAOH as a commercially available, efficient, mild, straightforward, simple, environmentally and economically friendly organo-basic catalyst for the synthesis of diverse Pyrano[2,3-d]pyrimidinone derivtives. Thus we have developed a novel, simple and highly efficient one potmulticomponent reaction protocol for the synthesis of Pyrano[2,3-d]pyrimidinone derivtives in ethanol:water solvent system.

---

• View Article
• PDF 718.09 K

Organic chemistry

Synthesis and characterization of 6-(hydroxymethyl)-14, 16-dimethyl-13, 14, 16, 17-tetrahydro-6H-13, 17-epiminodibenzo [e, l] [1, 4] dioxacyclotridecin-15 (7H)-one

Alireza Banaei; Soheyla Karimi; Negar Nurbageri

Volume 4, Issue 4, pp. 359-490, Serial No. 13 , October 2016, , Pages 359-363

Abstract

  New 6-(hydroxymethyl)-14, 16-dimethyl-13, 14, 16, 17-tetrahydro-6H-13, 17-epiminodibenzo [e, l] [1, 4] dioxacyclotridecin-15 (7H)-one (2a) was synthesized in good yield by the Petrenko–Kritchenko reaction of 2, 2'-((3-hydroxypropane-1, 2-diyl) bis (oxy)) bisbenzaldehyde (1a) with diethyl ketone ...  Read More New 6-(hydroxymethyl)-14, 16-dimethyl-13, 14, 16, 17-tetrahydro-6H-13, 17-epiminodibenzo [e, l] [1, 4] dioxacyclotridecin-15 (7H)-one (2a) was synthesized in good yield by the Petrenko–Kritchenko reaction of 2, 2'-((3-hydroxypropane-1, 2-diyl) bis (oxy)) bisbenzaldehyde (1a) with diethyl ketone in the mixture of ethanol and acetic acid as solvent in the presence of ammonium acetate. The compounds were characterized by elemental analyses, IR, 1H-NMR, 13C-NMR and mass spectrometry.Keywords: Petrenko–Kritchenko condensation, Macrocyclic compound, Bisaldehyde, 6-(hydroxymethyl)-14, 16-dimethyl-13, 14, 16, 17-tetrahydro-6H-13, 17-epiminodibenzo [e, l] [1, 4] dioxacyclotridecin-15 (7H)-one, 2, 2'-((3 hydroxypropane-1, 2-diyl) bis (oxy)) bisbenzaldehyde

---

• View Article
• PDF 206.72 K

Organic chemistry

An environmentally benign synthesis of aryl-hydrazones with aqueous extract of Acacia pods as a natural surfactant type catalyst

Hemant Vilas Chavan; Dnyaneshwar M. Sirsat; Yoginath B. Mule

Volume 4, Issue 4, pp. 359-490, Serial No. 13 , October 2016, , Pages 373-388

Abstract

  An environmentally benign and clean synthesis of aryl-hydrazones by reacting variety of carbonyl compounds with thiosemicarbazide, semicarbazide, aminoguanidine, and phenyl hydrazine has been achieved using aqueous extract of Acacia concinna pods as a natural surfactant type catalyst. We found that the ...  Read More An environmentally benign and clean synthesis of aryl-hydrazones by reacting variety of carbonyl compounds with thiosemicarbazide, semicarbazide, aminoguanidine, and phenyl hydrazine has been achieved using aqueous extract of Acacia concinna pods as a natural surfactant type catalyst. We found that the aqueous extract of Acacia concinna pods could be effectively used for the synthesis of aryl-hydrazones. This efficient process proceeds smoothly in aqueous medium at room temperature within a very short period of time. All the products were obtained by simple filtration. The low cost, easy availability of the catalyst and simple reaction conditions are the notable features of the present method.

---

• View Article
• PDF 313.87 K

Organic chemistry

A novel and efficient synthesis of bisindolyl methanes with using silica-supported 3-(triethoxysilyl) propane-1-ammonium chloride as reusable catalyst under solvent free conditions

Mohammad Reza Poor Heravi; Aazam Monfared Monfared; Masoumeh Ahmadi

Volume 4, Issue 4, pp. 359-490, Serial No. 13 , October 2016, , Pages 433-448

Abstract

  A facile and efficient synthesis of bis(indolyl)methanes derivatives (3a-u) was reported via a condensation reaction of aldehydes and indole in the presence of by silica-supported-3-(triethoxysilyl) propane-1-ammonium chloride catalysis under solvent free conditions. We studied the reaction in different ...  Read More A facile and efficient synthesis of bis(indolyl)methanes derivatives (3a-u) was reported via a condensation reaction of aldehydes and indole in the presence of by silica-supported-3-(triethoxysilyl) propane-1-ammonium chloride catalysis under solvent free conditions. We studied the reaction in different conditions and optimized. The use of just 0.02 g of (silica gel-ammonium salt) is sufficient. The reaction was carried out at 110 °C under thermal condition. This method, including some advantages such as mild reaction condition, easy work-up, and recoverable and reusable catalyst.A facile and efficient synthesis of bis(indolyl)methanes derivatives (3a-u) was reported via a condensation reaction of aldehydes and indole in the presence of by silica-supported-3-(triethoxysilyl) propane-1-ammonium chloride catalysis under solvent free conditions. We studied the reaction in different conditions and optimized. The use of just 0.02 g of (silica gel-ammonium salt) is sufficient. The reaction was carried out at 110 °C under thermal condition. This method, including some advantages such as mild reaction condition, easy work-up, and recoverable and reusable catalyst..

---

• View Article
• PDF 943.47 K

Organic chemistry

Prediction of boiling point and water solubility of crude oil hydrocarbons using sub-structural molecular fragments method

Faraidon Ghaderi; Saadi Saaidpour

Volume 4, Issue 4, pp. 359-490, Serial No. 13 , October 2016, , Pages 466-475

Abstract

  The quantitative structure–property relationship (QSPR) method is used to develop the correlation between structures of crude oil hydrocarbons (80 compounds) and their boiling point and water solubility. Sub-structural molecular fragments (SMF) calculated from structure alone were used to represent ...  Read More The quantitative structure–property relationship (QSPR) method is used to develop the correlation between structures of crude oil hydrocarbons (80 compounds) and their boiling point and water solubility. Sub-structural molecular fragments (SMF) calculated from structure alone were used to represent molecular structures. A subset of the calculated fragments selected using stepwise regression (forward and backward steps) (SR) was used in the QSPR model development. Multiple linear regressions (MLR) are utilized to construct the linear prediction model. The prediction results agrees well with the experimental values of these properties. The comparison results indicate the superiority of the presented models and reveal that it can be effectively used to predict the boiling point temperatures and water solubility values of crude oil hydrocarbons from the molecular structures alone. The stability and predictivity of the proposed models were validated using internal validation (leave one out and leave many out) and external validation. Application of the developed models to test set of 16 compounds demonstrates that the new models are reliable with good predictive accuracy and simple formulation.

---

• View Article
• PDF 275.99 K

Organic chemistry

A green and eco-friendly method for the synthesis of xanthene derivatives using cellulose sulfuric acid under solvent-free conditions

Seyyedeh Cobra Azimi; Esmayeel Abbaspour-Gilandeh

Volume 4, Issue 3, pp. 236-358, Serial No. 12 , July 2016, , Pages 245-255

Abstract

  A green and convenient method for the synthesis of 14-aryl-14H-dibenzo[a,i]xanthene-8,13-diones and spiro[dibenzo[a,i]-xanthene-14,3'-indoline]-2',8,13-triones in the presence of a catalytic amount of cellulose sulfuric acid (CSA) as an efficient biopolymer-based catalyst under solvent-free conditions ...  Read More A green and convenient method for the synthesis of 14-aryl-14H-dibenzo[a,i]xanthene-8,13-diones and spiro[dibenzo[a,i]-xanthene-14,3'-indoline]-2',8,13-triones in the presence of a catalytic amount of cellulose sulfuric acid (CSA) as an efficient biopolymer-based catalyst under solvent-free conditions at 100 °C is described. The condensation reactions of β-naphtol, 2-hydroxynaphthalene-1,4-dione with aldehydes or isatins to afford the corresponding xanthenes in good to excellent yields. To the best of our knowledge, it is the first example of a multicomponent reaction to the synthesis of these compounds using cellulose sulfuric acid. The present approach offers several advantages such as shorter reaction times, simple work-up, excellent yields, non-toxicity of the catalyst, and solvent-free conditions. Moreover, cellulose sulfuric acid is successfully reused for four cycles without significant less of activity.

---

• View Article
• PDF 249.39 K

Organic chemistry

An efficient solvent-free synthesis of 1,8-dioxo-octahydroxanthenes by using Fe2(SO4)3.7H2O as catalyst

Reyhaneh Khoeiniha; Ali Ezabadi; Abolfazl Olyaei

Volume 4, Issue 3, pp. 236-358, Serial No. 12 , July 2016, , Pages 273-282

Abstract

  A facile and efficient protocol for the synthesis of 1,8-dioxo-octahydroxanthenes has been developed by one-pot Knoevenagel condensation, Michael addition and cyclodehydration reaction of dimedone (active methylene carbonyl compound) with aromatic aldehydes in the presence of Iron (III) sulfate hydrate ...  Read More A facile and efficient protocol for the synthesis of 1,8-dioxo-octahydroxanthenes has been developed by one-pot Knoevenagel condensation, Michael addition and cyclodehydration reaction of dimedone (active methylene carbonyl compound) with aromatic aldehydes in the presence of Iron (III) sulfate hydrate as a solid acidic catalyst under solvent-free conditions. Various aromatic aldehydes were utilized in the reaction and in all situations the desired product were synthesized successfully. The present methodology is cost-effective in addition to other advantages like high yields of products in shorter reaction time and simple workup procedure. The non toxicity and easy availability of the catalyst makes this protocol efficient and environmentally benign.

---

• View Article
• PDF 125.41 K

Organic chemistry

(Carboxy-3-oxopropylamino)-3-propylsilylcellulose as a novel organocatalyst for the synthesis of coumarin derivatives under solvent-free conditions

Mehri Salimi

Volume 4, Issue 3, pp. 236-358, Serial No. 12 , July 2016, , Pages 295-308

Abstract

  In this research, (Carboxy-3-oxopropylamino)-3-propylsilylcellulose (COPAPSC) as an organocatalyst, has been synthesized by grafting of succinic anhydride on the NH2-modified cellulose (cellulose functionalized with 3- aminopropyltriethoxysilane). The –CO2H group-functionalized cellulose (COPAPSC) ...  Read More In this research, (Carboxy-3-oxopropylamino)-3-propylsilylcellulose (COPAPSC) as an organocatalyst, has been synthesized by grafting of succinic anhydride on the NH2-modified cellulose (cellulose functionalized with 3- aminopropyltriethoxysilane). The –CO2H group-functionalized cellulose (COPAPSC) is used as a catalyst for the synthesis of coumarin derivatives from the reaction of phenolic substrate and β- Keto-esters under solvent-free conditions. The results showed that the yield of products is between 85-94%. The advantages of this reaction include simple work-up, short reaction time, excellent yields as well as easily separation of catalyst. The catalyst can be reused several times in subsequent reactions without any decreasing in the catalyst reactivity.

---

• View Article
• PDF 233.6 K

Organic chemistry

Oxidative aromatization of some 1,4-dihydropyridine derivatives using NaBrO3

Masoomeh Abdoli-Senejani; Nilufar Foruzan; Mahnaz Bahmani; Tahereh Momeni Isfahani; Saba Dustepour

Volume 4, Issue 3, pp. 236-358, Serial No. 12 , July 2016, , Pages 309-317

Abstract

  In this study, oxidation of some 3,5-diacyl or 3,5-diester 1,4-dihydropyridines to corresponding pyridine derivatives using sodium bromate in the presence of NH4Cl, NaHSO4 and Bu4NHSO4 under thermal conditions has been investigated. The yield and structure of formed products is similar under all conditions; ...  Read More In this study, oxidation of some 3,5-diacyl or 3,5-diester 1,4-dihydropyridines to corresponding pyridine derivatives using sodium bromate in the presence of NH4Cl, NaHSO4 and Bu4NHSO4 under thermal conditions has been investigated. The yield and structure of formed products is similar under all conditions; however, the reaction is accelerated in the presence of Bu4NHSO4 and NaHSO4. In addition, oxidation of 3,5-diester 1,4-dihydropyridines, against 3,5-diacetyl 1,4-dihydropyridines using sodium bromate in the presence of tetrabutylammonium hydrogen sulfate, leads to the corresponding pyridines in shorter reaction times than sodium hydrogen sulfate. The cheapness of reagent, high yielding, easy work up and mild condition make this method a useful addition to the available methods in organic synthesis

---

• View Article
• PDF 123.04 K

Organic chemistry

An efficient green synthesis of highly substituted imidazoles catalyzed by Al-MCM-41 nanoreactors

Abolfazl Olyaei; Zohreh Derikvand; Fatemeh Noruzian; Mahdieh Sadeghpour

Volume 4, Issue 3, pp. 236-358, Serial No. 12 , July 2016, , Pages 337-346

Abstract

  Al-MCM-41 nanoreactors is found to be a remarkable efficient catalyst for one-pot multicomponent cyclocondensation of benzil, aniline or ammonium acetate and aromatic aldehydes for the synthesis of polysubstituted imidazoles under solvent-free conditions. The reaction was efficiently promoted by 10 mg ...  Read More Al-MCM-41 nanoreactors is found to be a remarkable efficient catalyst for one-pot multicomponent cyclocondensation of benzil, aniline or ammonium acetate and aromatic aldehydes for the synthesis of polysubstituted imidazoles under solvent-free conditions. The reaction was efficiently promoted by 10 mg nano-Al-MCM-41 and the heterogeneous catalyst was recycled for four runs in this reaction without losing its catalytic activity. The key advantages of this process are operational simplicity, reusable catalyst, shorter reaction time, convenient work-up procedures, avoiding the use of organic solvents and purification of products by non-chromatographic methods. By this advantage, several polysubstituted imidazoles as pharmaceutical important molecules can be prepared in high yield and high purity.

---

• View Article
• PDF 145.65 K