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Gas-phase diels-alder cycloaddition reaction in the presence of methanol and water vapor
, Article Journal of Physical Organic Chemistry ; Volume 16, Issue 1 , 2003 , Pages 79-83 ; 08943230 (ISSN) ; Talebi, B. A ; Sharif University of Technology
2003
Abstract
Hydrogen bonding effects of protic solvents, apart from bulk properties, on the reaction rate of the cycloaddition of cylopentadiene and vinyl acetate in the presence of water and methanol in the gas phase were investigated. The results showed that methanol increases the reaction rate in the gas phase more than the water. This is attributed to the stronger hydrogen bonding effect of methanol in this phase. Ab initio and semi-empirical calculations show that methanol stabilizes the transition state of the reaction more than water. This arises from two different origins, distribution of charge and geometry of the hydrogen bond. Copyright © 2002 John Wiley & Sons, Ltd
Multiparameter correlation of the rate of a [2 + 2] cycloaddition reaction versus solvophobicity parameter and normalized polarity parameter in aqueous solutions
, Article Journal of Physical Organic Chemistry ; Volume 13, Issue 8 , 2000 , Pages 468-472 ; 08943230 (ISSN) ; Habibi Yangjeh, A ; Sharif University of Technology
John Wiley and Sons Ltd
2000
Abstract
The second-order rate constants of the [2 + 2] cycloaddition reaction between diethyl azodicarboxylate and ethyl vinyl ether were obtained spectrophotometrically in various solvents and aqueous solutions of 1,4-dioxane and methanol at 30 ± 0.1 °C. In all media except aqueous solutions, a very good linear correlation of logk2 vs ETN (normalized polarity parameter) was obtained (n = 11, r = 0.991, s = 0.086). Because of the higher polarity of the activated complex relative to the reactants, the rate of the reaction increase with increasing solvent polarity parameter. Dual-parameter correlation of logk2 vs π* (dipolarity/polarizability) and a (hydrogen bonding acidity) also gives good results...
, M.Sc. Thesis Sharif University of Technology ; Matloubi Moghaddam, Firouz (Supervisor)
Abstract
1,3-Dipolar cycloaddition reactions constitute one of the most fundamental reactions for construction of five-membered heterocyclic compounds Spiro and dispirooxindoles have become important synthetic targets as these structural frameworks form the core units of many naturally occurring molecules that possess abundant biological activities .In this report we used (E)-Aryl ideneindolinones as unusual dipolarophiles for synthesis of dispirooxindoles. In follow different bifunctional nucleophiles for example 1,3-dicarbonyl, phenol, thioindole can be used in synthesis of benzoxazocines We have reported a new and efficient synthesis of benzoxazocines via unique tandem 1,3-dinucleophilic addition...
Study of Catalytic Activity of Zirconium-Based Metal-Organic Frameworks in the Epoxide Ring-Opening Reactions
, M.Sc. Thesis Sharif University of Technology ; Bagherzadeh, Mojtaba (Supervisor)
Abstract
In current research, two zirconium-based metal-organic frameworks, MIP-202 (Zr) and UIO-66(CO2H)2 were employed as catalysts in the epoxy ring-opening reactions by amino and alcoholic nucleophiles. Firstly, these metal-organic frameworks were prepared under mild synthetic conditions and then characterized by means of spectral techniques such as X-ray diffraction (XRD), nuclear magnetic resonance spectroscopy (NMR), Fourier transform infrared spectroscopy (FT-IR), electron microscopy Scanning (SEM) and X-ray energy diffraction (EDAX) spectroscopy were confirmed. Finally, their catalytic activity in epoxy ring-opening reactions was investigated and in to determine optimal conditions, the...
Synthesis of Thiopyrano Indole Annulated Benzo -δ-Sultones Via Domino Knoevenagele Hetero-Dielse Alder Reaction& Synthesis of Dispiro Compounds Via On-Pot Three Componet 1,3- Dipolar Cycloaddition
,
M.Sc. Thesis
Sharif University of Technology
;
Moghaddam, Matloubi
(Supervisor)
Abstract
The domino-Knoevenagele hetero-Dielse Alder reaction is an efficient synthesis of complex compounds like natural products from simple substrates and highly diverse molecules. In the first chapter, synthesis of pyran, pyranopyran, pyrano-thiopyran heterocycles and [6,5] pyranopyrrole derivatives are achieved via domino Knoevenagele hetero-Dielse Alder reaction of O-acrylated and o- propargylated salicylaldehyde derivatives with thiooxindole and 4- hydroxyl dithiocoumarin. We discovered a new and efficient synthesis of a great variety of thiopyrano indole annulated benzo -δ-sultones via domino Knoevenagele hetero-Dielse Alder reaction of thiooxindole derivatives and (E)-2-formylphenyl...
Synthesis of Spiro Heterocyclic Compounds by Using Isatin Based 1,3-Dipolar
, M.Sc. Thesis Sharif University of Technology ; Matloubi Moghaddam, Firouz (Supervisor)
Abstract
Today, heterocycle compounds have become increasingly important in organic chemistry syntheses. Many extracellular compounds have a confirmed biological property. Due to the high bioactivity of these compounds, the development of their synthetic methods has received considerable attention and numerous reports have been published on their synthesis. One of the most commonly used examples is terazosin. It was first marketed as a blood pressure lowering drug but was later used in the treatment of benign prostate gland.Another important class of these compounds may be the different derivatives of the pyrimidine molecule used in the treatment of cancer. The use of hetero- cyclic compounds is not...
Use of Suitable Methods in Synthesis of Spiropyrrolididne Oxindole, Polysubstituted Thiophene, Thiopyrano Benzosultone and Pyrimidines by Cycloaddition Reactions
, Ph.D. Dissertation Sharif University of Technology ; Matloubi Moghaddam, Firouz (Supervisor)
Abstract
We have reported a new and efficient synthesis of a broad spectrum of heterotetracyclic thiopyranoindole via knovenagel hetero diels alder reaction.Fused pyrimidines have attracted considerable attention in synthetic organic chemistry because of their wide range of biological activities pharmaceutical and therapeutic properties, and antibacterial, antiviral, antitumor, and anti-inflammatory activities. We have reported a new efficient method for synthesis of pyrimidines fused to coumarine, uracile, cyclohexane and triamino pyrimidine structures. The major benefits of the current study are high yields, short reaction times, mild reaction conditions and available materials..We have also...
, M.Sc. Thesis Sharif University of Technology ; Mtlobi Moghadam, Firouz (Supervisor)
Abstract
The one pot, three component 1,3-dipolar cycloaddition reaction of azomethine ylides with a series of new dipolarophiles (E)-3 -benzylidene- indolin-2 -ones in methanol under the reflux condition yields ,3′-dispiropyrrolidine oxindole library. The product is produced with high regioselectivity. Catalyst free, excellent yield , easy workup process, short reaction time, and convenient operation are the characteristics of this procedure. NMR and X-ray are used to determine the structure and stereochemistry of cycloadduct products.
1, 3- Dipolar Cycloaddition Reactions of Azomethine Ylides of Ninhydrin with Chalcones and Investigation of Asymmetric Addition of TMSCN to Imines
,
M.Sc. Thesis
Sharif University of Technology
;
Saidi, Mohammad Reza
(Supervisor)
;
Jadidi, Khosrow
(Supervisor)
;
Mehrdad, Morteza
(Co-Advisor)
Abstract
Part 1
1,3-dipolar cycloaddition reactions offer convenient routes for the construction of a variety of five-membered heterocycles. This thesis represents a simple synthetic method via 1,3-dipolar cycloaddition reaction to prepare a novel class of spiro pyrrolidines and spiro pyrrolizidines which exhibit many biological activities. Non-stabilized azomethine ylides which generated in situ by the decarboxylative condensation of ninhydrin with proline and sarcosine were used as a 1,3-dipoles. On the other hand, chalcone and its derivatives with an impressive array of pharmacological activities were the dipolarophiles in these reactions. The reactions were carried out through reflax...
1,3-dipolar cycloaddition reactions offer convenient routes for the construction of a variety of five-membered heterocycles. This thesis represents a simple synthetic method via 1,3-dipolar cycloaddition reaction to prepare a novel class of spiro pyrrolidines and spiro pyrrolizidines which exhibit many biological activities. Non-stabilized azomethine ylides which generated in situ by the decarboxylative condensation of ninhydrin with proline and sarcosine were used as a 1,3-dipoles. On the other hand, chalcone and its derivatives with an impressive array of pharmacological activities were the dipolarophiles in these reactions. The reactions were carried out through reflax...
Synthesis of Polycyclic Heterocycles using Benzofuranone Scaffolds via 1,3-Dipolar Cycloaddition Reactions under Green Chemistry Conditions
, Ph.D. Dissertation Sharif University of Technology ; Matloubi Moghaddam, Firouz (Supervisor) ; Foroumadi, Alireza (Co-Supervisor)
Abstract
Spirooxindole compounds are naturally occurring compounds and have significant biological activities due to their unique spatial structure. Spirooxindole compounds, especially spiro oxindoles containing acyclic ring at C-3 position of oxindole, have high interaction capability with large productions. Therefore, these compounds are important in medicinal chemistry. The method used for the synthesis of spirooxindole compounds has been introduced. In general, for the synthesis of these compounds, isatin derivatives are used in 1 and 3 dipolar reactions in the presence of various solvents and catalysts. Due to the presence of quaternary spiro carbon with sp3 hybridization in the structure of...
Highly efficient synthesis of pyrimido[4,5-d]pyrimidine-2,4-dione derivatives catalyzed by iodine
, Article Tetrahedron Letters ; 2014 , p. 4720-4723 ; Khodabakhshi, M. R ; Aminaee, M ; Sharif University of Technology
Abstract
A new and efficient synthesis of pyrimido[4,5-d]pyrimidine-2,4-dione derivatives through the reaction of 6-aminouracils and N,N′-bis(arylmethylidene) arylmethane in the presence of molecular iodine as a readily available and feasible catalyst
Kinetics study of a Diels-Alder reaction in mixtures of an ionic liquid with molecular solvents
, Article Journal of Physical Organic Chemistry ; Volume 21, Issue 9 , 2008 , Pages 783-788 ; 08943230 (ISSN) ; Habibi Yangjeh, A ; Gholami, M. R ; Sharif University of Technology
2008
Abstract
The second-order rate constants for cycloaddition reaction of cyclopentadiene with naphthoquinone were determined spectrophotometrically in various compositions of 1-(1-butyl)-3-methylimidazolium terafluoroborate ([bmim]BF4) with water and methanol at 25°C. Rate constants of the reaction in pure solvents are in the order of water > [bmim]BF 4 > methanol. Rate constants of the reaction decrease sharply with mole fraction of the ionic liquid in aqueous solutions and increase slightly to a maximum in alcoholic mixtures. Multi-parameter correlation of logk 2 versus solute-solvent interaction parameters demonstrated that solvophobicity parameter (Sp), hydrogen-bond donor acidity (α) and...
Molybdenum(VI) Complexes and Palladium Nanoparticles in Ionic Liquid-Liquid Biphasic and Supported Ionic Liquid phase (SILP) Catalysis, and Green Catalytic Processes using Polymeric Ionic Liquids (PILs
, Ph.D. Dissertation Sharif University of Technology ; Bagherzadeh, Mojtaba (Supervisor)
Abstract
In this thesis, ionic liquids and polymeric ionic liquids were investigated as solvent and support for immobilization of molybdenum and palladium catalysts. Three newly synthesized room temperature ionic liquids containing molybdate anion, [DMIm][MoO2(NCS)4], [RPy][MoO2(NCS)4] (R = butyl or decyl), and previously reported [BMIm][MoO2(NCS)4] were used as catalysts for the reduction of sulfoxides. For facilitating the recyclability of the catalysts, the ionic liquid solvents, [RMIm][PF6] and [RPy][PF6] (RMIm=1-n-alkyl-3-methylimidazolium, RPy= 1-n-alkylpyridinium), were applied to immobilize molybdenum catalysts. These catalysts showed high catalytic activity for sulfoxide reduction in this...
Immobilization of copper ions onto α-amidotriazole-functionalized magnetic nanoparticles and their application in the synthesis of triazole derivatives in water
, Article Applied Organometallic Chemistry ; Volume 30, Issue 6 , 2016 , Pages 488-493 ; 02682605 (ISSN) ; Ayati, S. E ; Firouzi, H. R ; Ghorbani, F ; Sharif University of Technology
John Wiley and Sons Ltd
Abstract
A new heterogeneous copper catalyst was synthesized by immobilization of copper ions onto magnetic nanoparticles with a new ligand based on triazole. The catalyst was characterized using scanning and transmission electron microscopies, atomic absorption and Fourier transform infrared spectroscopies, and thermogravimetric, elemental and energy-dispersive X-ray analyses. The results confirmed that a good level of organic groups was immobilized on the magnetic nanoparticles. Huisgen cycloaddition reaction was chosen as a model reaction for the investigation of catalyst activity under green conditions. Phenylacetylene and benzyl bromide derivatives were used for the synthesis of triazoles. The...
Biosynthesis of copper oxide nanoparticles with potential biomedical applications
, Article International Journal of Nanomedicine ; Volume 15 , 2020 , Pages 3983-3999 ; Bagherzadeh, M ; Kiani, M ; Ghadiri, A. M ; Etessamifar, F ; Jaberizadeh, A. H ; Shakeri, A ; Sharif University of Technology
Dove Medical Press Ltd
2020
Abstract
Introduction: In recent years, the use of cost-effective, multifunctional, environmentally friendly and simple prepared nanomaterials/nanoparticles have been emerged considerably. In this manner, different synthesizing methods were reported and optimized, but there is still lack of a comprehensive method with multifunctional properties. Materials and Methods: In this study, we aim to synthesis the copper oxide nanoparticles using Achillea millefolium leaf extracts for the first time. Catalytic activity was investigated by in situ azide alkyne cycloaddition click and also A3 coupling reaction, and optimized in terms of temperature, solvent, and time of the reaction. Furthermore, the...