Search for: michael-addition
Total 32 records
Synthesis and Characterization of Dithiocarbamate Complex Derivatives of 3-((Pyridin-2-yl)Methyl Amino)Propannitril, M.Sc. Thesis Sharif University of Technology ; Saeedi, Mohammad Reza ; Ziyaei Halimehjani, Azim
Dithiocabamates are valuable compounds due to their wide application as herbicides, fungicides, antitumor and etc. Another aspect of dithiocarbamates is their application in coordination chemistry. In this project, 3-((pyridin-2-yl) methyl amino) propane nitrile was prepared via Michael addition reaction of 1-methyl¬amino¬pyridine and acrylonitrile in water. Then this compound was converted to its potassium dithiocarbamate salt via treatment with carbon disulfide in the presence of potassium hydroxide in tetrahydrofuran. The prepared ligand was used in complexation with metal salts of Zn, Hg, Ni and Sn to prepare their dithiocarbamate complexes. The structure of complexes was elucidated by...
LiClO4 accelerated Michael addition of amines to α,β-unsaturated olefins under solvent-free conditions, Article Tetrahedron ; Volume 60, Issue 2 , 2004 , Pages 383-387 ; 00404020 (ISSN) ; Saidi, M. R ; Sharif University of Technology
Elsevier Ltd 2004
Several primary and secondary amines were added to α,β- unsaturated esters, nitriles, amides, and ketones to give the corresponding saturated amines mediated by solid lithium perchlorate under solvent-free and environmentally friendly conditions at room temperature. © 2003 Elsevier Ltd. All rights reserved
LiCO4/Et3N: Highly efficient and active catalyst for selective Michael addition of active methylene compounds under solvent-free condition, Article Journal of Molecular Catalysis A: Chemical ; Volume 292, Issue 1-2 , 2008 , Pages 44-48 ; 13811169 (ISSN) ; Azizi, N ; Akbari, E ; Ebrahimi, F ; Sharif University of Technology
A simple catalyst LiClO4/Et3N has been developed and demonstrated to efficiently catalyze Michael addition reactions of active methylene compounds to conjugated ketones, nitriles, esters and nitroalkenes with remarkably high yields and in short reaction time. The Michael addition to nitroalkenes and α,β-unsaturated ketones proceeds quantitatively in the usual way, giving the monoaddition product. © 2008 Elsevier B.V. All rights reserved
Solid lithium perchlorate-mediated conjugate addition of thiols and indoles to α,β-unsaturated carbonyl compounds, Article Journal of Sulfur Chemistry ; Volume 26, Issue 3 , 2005 , Pages 251-259 ; 17415993 (ISSN) ; Saidi, M. R ; Sharif University of Technology
A simple, efficient, and general synthetic strategy has been developed for the synthesis of Michael adducts in the presence of solid lithium perchlorate under solvent-free conditions. Nucleophilic addition of thiols and indoles gave the corresponding Michael adducts in high yields. © 2005 Taylor & Francis
An efficient one-pot Michael addition of dithiocarbamate anion to α,β-unsaturated olefins mediated by lithium perchlorate, Article Journal of Sulfur Chemistry ; Volume 26, Issue 2 , 2005 , Pages 149-153 ; 17415993 (ISSN) ; Saidi, M. R ; Sharif University of Technology
Taylor and Francis Ltd 2005
The reaction of substituted dithiocarbamates with electrophilic alkenes in the presence of LiClO4 was investigated in an attempt to prepare numerous ethyl dithiocarbamates bearing β-electron-withdrawing-group substituents. The reaction conditions are mild, neutral, with extremely simple work-up procedures, and offer high yield. © 2005 Taylor & Francis Group Ltd
M.Sc. Thesis Sharif University of Technology ; Mahmoudi Hashemi, Mohammad ; Ziyaei Halimehjani, Azim
Dithiocarbamates are a group of compounds that nowadays have been used extensively in pharmaceutical agents, organicsynthesis and as fungicides in agriculture.We haveshown, an efficient. regiospecific method for the synthesis of cyclic dithiocarbamates by one-pot three-component cascade reaction of an amine, CS2 and α,β-unsaturated aldehyde via Michael addition/hemiamination reaction in watre under a mild and green procedure with excellent yields and complete regioselectivity
Synthesis of β- Amino Carbonyl Compounds in Solvent-free Condition in the Presence of SiCl4 And Synthesis of Benzothiazole Derivatives, M.Sc. Thesis Sharif University of Technology ; Mahmoodi Hashemi, Mohammad ; Azizi, Najmeddin
SiCl4 catalyzed Michael addition reaction of aliphatic and aromatic amines with different α,β- unsaturated compounds and one-pot three component Mannich reaction under solvent-free condition were investigated. β-amino carbonyl compound were synthesized in high yield in short reaction time. Furthermore, in the Mannich reaction good yield and excellent stereoselectivity were observed. In addition, the synthesis of 2-substituted benzothiazoles from aromatic aldehydes and 2 aminothiophenol in moderate to excellent yields in water in the presence of PTSA catalyst (10 mol%). This method provides a simple and efficient protocol in terms of mild reaction conditions, clean reaction profiles, small...
Article Synthetic Communications ; Volume 43, Issue 5 , May , 2013 , Pages 744-748 ; 00397911 (ISSN) ; Karimi, N ; Saidi, M. R ; Sharif University of Technology
Michael addition reaction of anthrone to nitroolefins is described in water without using any catalyst to prepare 9-(2-nitro-1-arylethyl)anthracene-10(9H)- ones. This method is green and efficient and gives good yields of products. The solvent effect is also investigated
Synthesis and characterization of metal dithiocarbamate derivatives of 3-((pyridin-2-yl)methylamino)propanenitrile: Crystal structure of [3-((pyridin-2-yl)methylamino)propanenitrile dithiocarbamato] nickel(II), Article Polyhedron ; Volume 102 , 2015 , Pages 643-648 ; 02775387 (ISSN) ; Torabi, S ; Amani, V ; Notash, B ; Saidi, M. R ; Sharif University of Technology
Elsevier Ltd 2015
Four metal dithiocarbamate complexes (Zn, Ni, Hg and Sn) based on an amine containing pyridyl and nitrile groups, 3-((pyridin-2-yl)methylamino)propanenitrile, were prepared and characterized by their elemental analysis, spectroscopic data (such as IR, 1H and 13C NMR), TGA analysis and X-ray crystallography of the Ni(II) complex. The presence of a band in the 1000 cm-1 region in the IR spectra, without any splitting, confirms the symmetrical bidentate bonding mode of the dithiocarbamate ligand. Also, the short thioureide C=N distance in the X-ray analysis of the Ni complex confirms the delocalization of π electrons over the S2CN moiety and strong double bond character between the carbon and...
Waste-free and environment-friendly uncatalyzed synthesis of dithiocarbamates under solvent-free conditions, Article Synlett ; Issue 18 , 2007 , Pages 2797-2800 ; 09365214 (ISSN) ; Ebrahimi, F ; Aakbari, E ; Aryanasab, F ; Saidi, M.R ; Sharif University of Technology
A mild, convenient, and practical one-pot procedure for the direct synthesis of dithiocarbamates has been developed by condensation of amines, CS2, and a Michael acceptor, under solvent-free conditions at room temperature in good to excellent yields. © Georg Thieme Verlag Stuttgart
A new imidazole-containing imidazolidinone catalyst for organocatalyzed asymmetric conjugate addition of nitroalkanes to aldehydes, Article Advanced Synthesis and Catalysis ; Volume 349, Issue 4-5 , 2007 , Pages 740-748 ; 16154150 (ISSN) ; Hartikka, A ; Matloubi Moghaddam, F ; Arvidsson, P. I ; Sharif University of Technology
Wiley-VCH Verlag 2007
Herein we report a new organocatalyst for the asymmetric Michael addition of nitroalkanes to α,β-unsaturated aldehydes. This catalyst incorporates a basic imidazole group in addition to the secondary amine responsible for activation of the α,β-unsaturated carbonyl compounds via iminium ion formation. The new organocatalyst is capable of catalyzing the enantioselective carbon-carbon bond formation with a high degree of enantiocontrol providing products in enantiomeric excesses of up to 92% and yields of up to to 91 %. These results constitute the best results so far reported for organocatalyzed Michael additions of nitroalkanes to α,β-unsaturated aldehydes, and provide proof of principle that...
Nucleophilic addition of thiaproline to electrochemically derived o-quinone, application to the sensitive voltammetric detection of thiaproline, Article Electroanalysis ; Volume 18, Issue 22 , 2006 , Pages 2225-2231 ; 10400397 (ISSN) ; Amiri, M ; Sharif University of Technology
The mechanism of electrochemical behavior of catechol in the presence of thiaproline is investigated by cyclic voltammetry, controlled-potential coulometry and spectrophotometric tracing of the reaction coordinate. The results indicate that thiaproline participate in with an ECEC mechanism in a nucleophilic (Michael) addition to o-quinone. Effect of pH of buffer solution on reaction pathway is studied and showed that addition of thiaproline to the o-quinone is performed only in solutions with pHs higher than 5. These results indicate that the addition of thiaproline is occurred first from amine functional group. In the second step, the addition of carboxylate group of thiaproline to C-5 of...
Article Letters in Organic Chemistry ; Volume 3, Issue 2 , 2006 , Pages 157-160 ; 15701786 (ISSN) ; Bardajee, G. R ; Taimoory, S. M. D ; Sharif University of Technology
KF/Al2O3 efficiently catalyzes aza-Michael addition of indole and 3-methylindole to a variety of electron-deficient conjugated alkenes such as α,β-unsaturated ketones, amides and nitriles. The N-alkylation adducts are produced in good to excellent yields and relatively in short times. The catalyst can be recycled for subsequent reactions without any appreciable loss of efficiency. © 2006 Bentham Science Publishers Ltd
Ethylenediamine grafting to functionalized NH2-UiO-66 using green aza-Michael addition reaction to improve CO2/CH4 adsorption selectivity, Article Industrial and Engineering Chemistry Research ; Volume 57, Issue 20 , April , 2018 , Pages 7030-7039 ; 08885885 (ISSN) ; Ahmadi Joukani, F ; Shojaei, A ; Sharif University of Technology
American Chemical Society 2018
Three versions of zirconium-based metal organic frameworks, NH2-UiO-66, GMA-UiO-66, and EDA-UiO-66, were synthesized and employed as adsorbent for CO2/CH4 separation. GMA-UiO-66 was synthesized via a ring opening reaction between the amine species in the framework and epoxy groups in glycidyl methacrylate (GMA), while the green aza-Michael addition reaction was used for the first time to functionalize GMA-UiO-66 with ethylenediamine (EDA). The products were characterized by BET, XRD, TGA, FESEM, ICP-OES, 1H NMR, mass spectroscopy, and FTIR-ATR methods to monitor their textural properties before and after functionalization. The results indicated that GMA was successfully grafted to the...
Michael-addition-initiated chemoselective three-component reaction for the synthesis of 2-(3-oxo-1,3-diarylpropyl)malononitrile derivatives using cerium(iv) ammonium nitrate in phosphorus ionic liquid, Article Polycyclic Aromatic Compounds ; 2021 ; 10406638 (ISSN) ; Batooie, N ; Mousavi, R ; Miraghaee, S ; Hosseinzadeh, N ; Mousavian, M ; Hoshyari, A ; Sajadimajd, S ; Mohammadi, B ; Hatami, R ; Sharif University of Technology
Taylor and Francis Ltd 2021
The aim of this research is the study of hexyltriphenylphosphonium bromide (HTPB) ionic liquid as a bifunctional promoter (solvent and catalyst) in the presence of cerium(IV) ammonium nitrate as a single electron oxidant for the Michael reaction at room temperature and solvent-free conditions. A novel, one-pot and environmentally benign the process to achieve the chemoselective of 2-(3-oxo-1,3-diarylpropyl)malononitrile derivatives instead of 2-(1,3-diarylallylidene)malononitriles using a three-component reaction involving acetophenone derivatives, various aromatic aldehydes and malononitrile was developed. This protocol is simple and provides biologically interesting products in good...
Michael Addition of Anthrone to Nitroolefines in Water and Oxidation of Alkenes Using a Supported Iron Oxide Nanocatalyst
Sharif University of Technology
Saeedi, Mohammad Reza
Ziyaei Halimehjani, Azim
This projct includes the following sections: In the first section, Michael addition reaction of anthrone to nitroolefins is described in water without using any catalyst to prepare 9-(2-nitro-1-arylethyl)anthracene-10(9H)-ones. This method is green, efficient and gives high yields of products. The solvent effect is also investigated. In the second section, Considerable efforts have been directed in recent years towards the transition metal complex catalyzed oxidation of organic compounds such as olefins, sulfides, benzylics alcohols and phenolics. And due to the various advantages of supported heterogeneous catalysts and in our aim to develop a simple, more efficient and eco-friendly...
M.Sc. Thesis Sharif University of Technology ; Mahmoudi Hashemi, Mohammad
This thesis contains two parts .In the first part a catalyst such as AlCl3/Al20 has been demonstrated to catalyze Michael addition reaction of amines to a,�- unsaturated compounds with high yields , short reaction time and under solvent-free condition.The Michael addition to a,�- unsaturated compounds produces quantitively the mono addition products.The next part is about olefins epoxidation . Alkene epoxidation is a useful reaction in organic synthesis. Epoxides play an important role in industrial intermediates for the production of fine chemicals as well as pharmaceuticals .The hydrogen peroxide has been used as an oxidant because it is considered as an economical and appropriate reagent...
Synthesis of Dithiocarbamate Salts, Reaction of Divinyl Sulfone with Amines and CS2 & Polymerization of Diamines and CS2 with Michael Acceptors, M.Sc. Thesis Sharif University of Technology ; Mahmoodi Hashemi, Mohammad ; Ziyaei Halimjani, Azim
At the first part of project, different kinds of monodithiocarbamates were synthesized.In order to prepare these compounds two methods have been used:Reactions of amines and carbon disulfide in water and finally addition of Michael acceptors.Reaction of amines and carbon disulfide, then addition of alkyl halides under solvent-free conditions.Dithiocarbamate salts are prepared in ether by using CF3SO3CH3 as the methylation agent with resulted monodithiocarbamates at the first part of the project. These salts are found to be ionic liquids, which is important class of organic compounds.At the second part of project, the Michael additions of amines with divinyl sulfone are investigated in...
Article Tetrahedron Asymmetry ; Volume 20, Issue 21 , 2009 , Pages 2429-2431 ; 09574166 (ISSN) ; Mirjafary, Z ; Saeidian, H
The first asymmetric synthesis of α,β-disubstituted γ-phosphono sulfonates is reported. The key step is the Michael addition of a lithiated enantiopure sulfonate bearing an inexpensive chiral sugar auxiliary to α,β-unsaturated phosphonates in good diastereoselectivities. After chromatographic purification, the cleavage of the chiral sugar auxiliary proceeds without any epimerization or racemization to form the corresponding isopropyl sulfonate in very good overall yield (75%) and excellent diastereomeric and enantiomeric excess (de, ee ≥ 95%). © 2009 Elsevier Ltd. All rights reserved
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
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