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One-pot Three-component route for the synthesis of functionalized 4H-chromenes catalyzed by ZrOCl2·8H2O in water
, Article Journal of Heterocyclic Chemistry ; Volume 55, Issue 2 , 2018 , Pages 522-529 ; 0022152X (ISSN) ; Keshavarzi, N ; Sharif University of Technology
HeteroCorporation
2018
Abstract
An efficient method for the synthesis of functionalized 4H-chromenes via a one-pot three-component condensation reaction of a 2-hydroxybenzaldehyde with an active methylene compound and a carbon-based nucleophile in the presence of a catalytic amount of ZrOCl2·8H2O in water under thermal condition has been described. High yields, simple work-up procedure, performing reactions in water and synthesis of complex molecules with a one-pot procedure are the main advantages of this procedure. In addition, the structure of the product from the condensation of salicylaldehyde, 2-naphthol, and dimedone was confirmed by X-ray crystallography. © 2018 Wiley Periodicals, Inc
The chemistry of 2-hydroxy-β-nitrostyrenes: versatile intermediates in synthetic organic chemistry
, Article Organic and Biomolecular Chemistry ; Volume 21, Issue 13 , 2023 , Pages 2653-2688 ; 14770520 (ISSN) ; Ghaffari, Z ; Sharif University of Technology
Royal Society of Chemistry
2023
Abstract
The applications of 2-hydroxy-β-nitrostyrenes as efficient bifunctional intermediates in organic synthesis are investigated in this review. For this purpose, reactions of 2-hydroxy-β-nitrostyrenes with diverse molecules, including carbonyl compounds, 1,3-dicarbonyl compounds, α,β-unsaturated carbonyl compounds, hemiacetals, nitroalkenes, γ-butenolides, tetronic acid, azalactones, pyrazolones, enamines, malononitrile, methyleneindolinones, ylides, etc., were investigated to construct interesting biologically active scaffolds such as chromans, chromenes, coumarins, benzofurans and their fused and spiro rings, natural products, and other useful cyclic and acyclic compounds. The main focus is on...
Bromonitroalkenes as efficient intermediates in organic synthesis
, Article Organic and Biomolecular Chemistry ; Volume 22, Issue 24 , 2024 , Pages 4801-4838 ; 14770520 (ISSN) ; Tahvildari, H ; Sharif University of Technology
2024
Abstract
Bromonitroalkenes are useful molecules in synthetic organic chemistry. They are mainly prepared from nitroalkenes via bromination reactions. In this review, the application of bromonitroalkenes as partners in the reaction with a diversity of mono- and bi-functional molecules, including aldehydes and ketones, active methylene compounds, 1,2-dicarbonyls, enamines, enols, electron-rich arenes, amidines, azomethine ylides, azirines, diazo compounds, and many others, is reviewed. By using these substrates, various biologically active scaffolds, such as heterocycles, carbocycles, spirocycles, polycyclic systems, natural products, and other useful acyclic compounds, were prepared. In addition, due...
Synthesis of aza-Henry products and enamines in water by Michael addition of amines or thiols to activated unsaturated compounds
, Article Tetrahedron Letters ; Volume 49, Issue 7 , 2008 , Pages 1244-1248 ; 00404039 (ISSN) ; Saidi, M. R ; Sharif University of Technology
2008
Abstract
Nitroamines and nitrothiols were synthesized in high yields by the Michael addition of amines and thiols to nitroolefins without using any catalyst. Also, the reaction of amines with dimethylacetylene dicarboxylate (DMAD) in water afforded the corresponding enamines. © 2007 Elsevier Ltd. All rights reserved
Investigating Mechanism, Transition State, and Products Distribution of Catalys-Free Hydrothiolation Reactions of Unactivated Terminal Alkynes by Dithiocarbamic Acids
, M.Sc. Thesis Sharif University of Technology ; Ziyaei Halimehjani, Azim (Supervisor)
Abstract
In this study, catalyst-free hydrothiolation reactions of unactivated terminal alkynes by dithiocarbamic acids have been investigated via computational chemistry approach and by Gaussian 09, GaussVeiw 5.0, and Spartan '14 V1.1.4 software from the perspective of the reaction mechanism, transition state, and the distribution of products. The calculation results have shown that the various in situ produced dithiocarbamic acids addition to unactivated terminal alkynes in which the alkyl group attached to the carbon 2 is an aliphatic hydrocarbon alkyl is through Markovnikov type path and this product is thermodynamically more stable which is in agreement with the experimental results. The NBO...
Synthesis of 1,3-thiazolidine-2-thiones using CS2 and epoxy amines
, Article Tetrahedron Letters ; Volume 152 , 2024 ; 00404039 (ISSN) ; Noorakhtar, F ; Marjani, Z ; Sharif University of Technology
2024
Abstract
An efficient method for the synthesis of 5-(hydoxymethyl)-1,3-thiazolidine-2-thiones is developed via the reaction of carbon disulfide with N-alkyl(aryl) epoxy amines. The reaction proceeds via intramolecular epoxide ring opening with in situ prepared dithiocarbamic acid. The products were obtained in good to high yields. © 2024 Elsevier Ltd
Catalyst-free regioselective ring opening of epoxides with aromatic amines in water and solvent-free conditions
, Article Journal of the Iranian Chemical Society ; Volume 10, Issue 1 , February , 2013 , Pages 7-11 ; 1735207X (ISSN) ; Gholami, H ; Saidi, M. R ; Sharif University of Technology
2013
Abstract
Without using any catalysts, a variety of epoxides undergo ring-opening by aromatic amines to afford the corresponding 1,2-amino alcohols in high to excellent yields with good regioselectivity in the presence of water as solvent and under solvent-free conditions
Highly efficient and catalyst-free synthesis of unsymmetrical thioureas under solvent-free conditions
, Article Tetrahedron Letters ; Volume 50, Issue 1 , 2009 , Pages 32-34 ; 00404039 (ISSN) ; Pourshojaei, Y ; Saidi, M. R ; Sharif University of Technology
2009
Abstract
A highly efficient and simple synthesis of unsymmetrical thioureas is reported based on the reaction of readily synthesized dithiocarbamates with amines, without using any catalyst under solvent-free conditions. The short reaction time, high yields, and solvent-free conditions are advantages of this method. We did not observe the formation of any symmetric disubstituted thiourea, under these reaction conditions. © 2008 Elsevier Ltd. All rights reserved
Regiospecific iodocyclization of S-allyl dithiocarbamates: synthesis of 2-imino-1,3-dithiolane and 2-iminium-1,3-dithiolane derivatives
, Article Tetrahedron Letters ; Volume 50, Issue 23 , 2009 , Pages 2747-2749 ; 00404039 (ISSN) ; Maleki, H ; Saidi, M. R ; Sharif University of Technology
2009
Abstract
4-Alkyl-2-imino-1,3-dithiolanes and 4-alkyl-2-iminium-1,3-dithiolanes were prepared in excellent yields with complete regiospecificity under mild conditions by the iodocyclization of S-allyl dithiocarbamates. Dehydrohalogenation of the 4-alkyl-2-imino-1,3-dithiolanes gave 4-alkylidene-2-imino-1,3-dithiolanes in excellent yields. © 2009 Elsevier Ltd. All rights reserved
Catalyst-free Friedel-Crafts alkylation of naphthols with nitrostyrenes in the presence of water
, Article Tetrahedron Letters ; Volume 50, Issue 13 , 2009 , Pages 1441-1443 ; 00404039 (ISSN) ; Aryanasab, F ; Saidi, M. R ; Sharif University of Technology
2009
Abstract
Accelerated Michael-type Friedel-Crafts alkylation of naphthols with nitrostyrenes in the presence of water is reported. The procedure is simple, catalyst-free, and affords good yields of the products. © 2009 Elsevier Ltd. All rights reserved
Synthesis of Different Allenamide Derivatives by using Selective Solvent in Green Chemistry
,
M.Sc. Thesis
Sharif University of Technology
;
Ziyaei Halimehjani, Azim
(Supervisor)
Abstract
Dithiocarbamates have diverse applications in the synthesis of organic compounds. Owing to their nucleophilic character, they can react with various electrophiles to furnish a wide range of useful products. In this project, one step and three component hydrothiolation of allenamides using dithiocarbamic acids generated in situ was investigated for the synthesis of allyldithiocarbamates. A broad scope of primary and secondary amines, as well as allenamides bearing both electron withdrawing and electron donating substituents, was explored. The reaction proceeds under catalyst-free and outstanding regio and stereoselectively, delivering good to excellent yields. The protocol is...
Catalyst/Metal/Solvent-free markovnikov hydrothiolation of unactivated alkenes with dithiocarbamic acids
, Article Journal of Organic Chemistry ; Volume 89, Issue 8 , 2024 , Pages 5353-5362 ; 00223263 (ISSN) ; Dağalan, Z ; Marjani, Z ; Gündüz, F ; Daştan, A ; Nişancı, B ; Sharif University of Technology
2024
Abstract
Catalyst-free Markovnikov-selective hydrothiolation of unactivated alkenes still remains a great challenge. Herein, we develop a catalyst/metal/solvent-free methodology for the Markovnikov hydrothiolation of unactivated alkenes with in situ prepared dithiocarbamic acids, providing a wide array of alkyl dithiocarbamates. A variety of terminal, internal, cyclic, and acyclic unactivated alkenes were applied successfully in this protocol. This three-component thiol-ene reaction can be considered as a new family of click reactions. © 2024 American Chemical Society
Dithiocarbamates as an efficient intermediate for the synthesis of 2-(alkylsulfanyl)thiazoles in water
, Article Tetrahedron Letters ; Volume 57, Issue 8 , 2016 , Pages 883-886 ; 00404039 (ISSN) ; Hasani, L ; Ali Alaei, M ; Saidi, M.R ; Sharif University of Technology
Elsevier Ltd
2016
Abstract
A simple, green and high-yielding procedure for the synthesis of 4-substituted-2-(alkylsulfanyl)thiazoles from the reaction of dithiocarbamates and α-halocarbonyl containing compounds in water is described. Also, a one-pot, two-step procedure for the synthesis of 2-(alkylsulfanyl)thiazoles from acetophenone and dithiocarbamates was developed. © 2016 Elsevier Ltd. All rights reserved
A simple and novel eco-friendly process for the synthesis of cyclic dithiocarbonates from epoxides and carbon disulfide in water
, Article Journal of Heterocyclic Chemistry ; Volume 46, Issue 2 , 2009 , Pages 347-350 ; 0022152X (ISSN) ; Ebrahimi, F ; Azizi, N ; Saidi, M. R ; Sharif University of Technology
2009
Abstract
The reaction of oxiranes with carbon disulfide for preparation of cyclic dithiocarbonates was carried out in water under catalytic amount of an organic base such as dimethylaminopyridine or triethylamine. The reaction conditions are simple and give high yields of desired products.© 2009 HeteroCorporation
Dithiocarbamate as an efficient intermediate for the synthesis of 2-(alkylthio)thiazol-4(5H)-ones
, Article Journal of Sulfur Chemistry ; Volume 37, Issue 5 , 2016 , Pages 529-536 ; 17415993 (ISSN) ; Alaei, M. A ; Soleymani Movahed, F ; Jomeh, N ; Saidi, M. R ; Sharif University of Technology
Taylor and Francis Ltd
2016
Abstract
An effective approach for the synthesis of 2-(alkylthio)thiazol-4(5H)-ones from alkyl dithiocarbamates and chloroacetyl chloride in the presence of NaHCO3 has been developed. Good to excellent yields of products, simple reaction conditions and general applicability are the most important advantages of this protocol
Investigation of the reaction of dithiocarbamic acid salts with aromatic aldehydes
, Article Organic Letters ; Volume 14, Issue 15 , July , 2012 , Pages 3838-3841 ; 15237060 (ISSN) ; Hajiloo Shayegan, M ; Hashemi, M. M ; Notash, B ; Sharif University of Technology
ACS
2012
Abstract
A reaction of dithiocarbamic acid salts with carbonyl compounds was investigated for the first time in the presence of BF 3•OEt 2. The reaction is temperature dependent and gives gem-bis(dithiocarbamates) at 35-45 °C as a molecule with high equivalents of dithiocarbamate groups. At lower temperatures (15-20 °C), the 2-iminium-1,3-dithietane is obtained as the only product. The structure of a 2-iminium-1,3-dithietane was accomplished by X-ray crystallographic analysis
Improvement in dye and lead removal efficiency of PES membranes by blending sulfur containing adsorbent nanomaterials
, Article Journal of Environmental Chemical Engineering ; Volume 12, Issue 5 , 2024 ; 22133437 (ISSN) ; Soylu, S ; Osman, D ; Tuncay, G ; Mobaraki, A ; Marjani, Z ; Ziyaei Halimehjani, A ; Koyuncu, I ; Sharif University of Technology
2024
Abstract
The study examines the synthesis and characterization of novel Fe3O4@SiO2@PrEDAS nanoparticles (NP) as a magnetic adsorbent and its application in polyethersulfone (PES) ultrafiltration (UF) membrane fabrication using the phase inversion method by adding it into the membrane dope solution at different concentrations. The efficiency of Fe3O4@SiO2@PrEDAS adsorbent was evaluated by batch adsorption of Pb(II). The performance of the modified membranes was investigated by determining the pure water flux (PWF), bovine serum albumin (BSA) rejection, Pb(II) removal, dye rejection, and antifouling characteristics. Considering the results, it was observed that the NP is an effective adsorbent for...
Michael Addition of Aromatic Amines and Synthesis Some Derivatives of Thiomorpholins
, M.Sc. Thesis Sharif University of Technology ; Mahmoudi Hashemi, Mohammad (Supervisor) ; Ziyaei Halimehjani, Azim (Supervisor)
Abstract
This project investigates on synthesis of β-amino carbonyl compounds with new approach to become closer to green chemistry principals.In this project, we investigated the synthesis of β-amino carbonyl compounds with aromatic amines and electron deficient alkenes in the Michael reaction using boric acid and glycerol in water as a green media. High yields of the products and easy handling are some advantages of this procedure. Also, we investigated the Michael reaction in different solvents and temperatures but gave better results in the aqueous media. Moreover, thiomorpholine derivatives were synthesized using this method to give excellent yield.
Synthesis of Dithiocarbamate by Markonikov Addition Reaction
, M.Sc. Thesis Sharif University of Technology ; Mahmoodi Hashemi, Mohammad (Supervisor) ; Ziyaei Halimehjani, Azim (Supervisor)
Abstract
Development of strategically important processes which are environmentally benign with simple methodology and work-up by low toxic material is currently reciving considerable attention.In recent years, dithiocarbamates (DTCs) and their synthesis with a green procedure have received many attention because of their undeniable applications.These synthetic compounds play important roles either in academia and industry. Here a simple, efficient and regiospecific method for synthesis of dithiocarbamates is described by one-pot three-component reaction of an amine, CS2 and alkyl vinyl ether via Markovnikov addition reaction in poly ethylene glycol (PEG) under a mild and green procedure with...
Synthesis of Dithiocarbamate Derivatives and Aminolysis of Epoxides in Water and under Different Conditions
, M.Sc. Thesis Sharif University of Technology ; Saeedi, Mohammad Reza (Supervisor) ; Ziyaei Halimehjani, Azim (Supervisor)
Abstract
This research project contains two parts that investigating new approaches for becoming closer to green chemistry principals is clear in it. In the first part we tried to synthesis dithiocarbamate salts using aromatic amins and than Michael addition of them to prepare bifunctional dithiocarbamats. But we found ?-thiols as final product. In the second part of this project, we investigated the regioselective epoxide ring opening with aromatic amines by using boric acid and glycerol in water as a green media. Corresponding ?-amino alcohols were obtained with excellent yields and considerable regioselectivity. High yields of the products, mild reaction conditions, using green catalyst and water...