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    PTSA-catalyzed cyclization of 6-aminouracils with diimines: Efficient synthesis of functionalized tetrahydropyrimido[4,5-d]pyrimidine-2,4-diones

    , Article ChemistrySelect ; Volume 3, Issue 41 , 2018 , Pages 11671-11676 ; 23656549 (ISSN) Khodabakhshi, M. R ; Kiamehr, M ; Matloubi Moghaddam, F ; Villinger, A ; Langer, P ; Sharif University of Technology
    Wiley-Blackwell  2018
    Abstract
    A new and efficient method has been developed for the synthesis of 5,7-diaryl-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidine-2,4-dione derivatives by cyclization of 6-aminouracils with N,N′-bis(arylmethylidene)arylmethanes (diimines). The products were formed in good yields and with very good anti-diastereoselectivity. The best yields were obtained when p-toluenesulfonic acid (PTSA) was used as the catalyst. The solvent also played an important role in the optimization. An amino-substituted 6-aminouracil and a corresponding sulfur analog could be successfully employed. In addition, various diimines, electron rich and neutral, could be successfully employed. The products are of relevance as... 

    Tandem dinucleophilic cyclization of cyclohexane-1,3-diones with pyridinium salts

    , Article Beilstein Journal of Organic Chemistry ; Volume 9 , 2013 , Pages 1119-1126 ; 18605397 (ISSN) Kiamehr, M ; Moghaddam, F. M ; Mkrtchyan, S ; Semeniuchenko, V ; Supe, L ; Villinger, A ; Langer, P ; Laroshenko, V. O ; Sharif University of Technology
    2013
    Abstract
    The cyclization of cyclohexane-1,3-diones with various substituted pyridinium salts afforded functionalized 8-oxa-10-aza-tricyclo[7.3.1.0 2,7]trideca-2(7),11-dienes. The reaction proceeds by regioselective attack of the central carbon atom of the 1,3-dicar-bonyl unit to 4-position of the pyridinium salt and subsequent cyclization by base-assisted proton migration and nucleophilic addition of the oxygen atom to the 2-position, as was elucidated by DFT computations. Fairly extensive screening of bases and additives revealed that the presence of potassium cations is essential for formation of the product  

    The synthesis of dibenzazocines via tandem dinucleophilic addition of phenols to quinolinium salts

    , Article Arkivoc ; Volume 2010, Issue 11 , Sep , 2010 , Pages 91-100 ; 1551-7012 (ISSN) Moghaddam, F. M ; Saeidian, H ; Kiamehr, M ; Mirjafary, Z ; Taheri, S ; Sharif University of Technology
    Arkat  2010
    Abstract
    Dibenzazocines were prepared via tandem dinucleophilic addition of phenols to quinolinium salts in good yields. The procedure is efficient, simple and the substrates are easily available  

    Calixarene based ionic liquid as an efficient and reusable catalyst for one-pot multicomponent synthesis of polysubstituted pyridines and BIS-pyridines

    , Article ChemistrySelect ; Volume 4, Issue 19 , 2019 , Pages 5903-5910 ; 23656549 (ISSN) Alishahi, N ; Mohammadpoor Baltork, I ; Tangestaninejad, S ; Mirkhani, V ; Moghadam, M ; Kia, R ; Sharif University of Technology
    Wiley-Blackwell  2019
    Abstract
    In this work, a calixarene based ionic liquid was successfully prepared and characterized by different techniques. This ionic liquid was used as an efficient catalyst for the synthesis of a series of polysubstituted pyridines from aldehydes, malononitrile, 1,3-diketones and arylamines in water as a green solvent. Also, for the first time, symmetric and unsymmetric polysubstituted bis-pyridines were obtained in high yields from diamines using this catalyst. Mild reaction conditions, high to excellent yields, easy work-up, excellent activity and reusability of the catalyst are the key features of this method which make it an interesting and novel alternative for the synthesis of the above... 

    The performance of phthalimide-N-oxyl anion

    , Article Monatshefte fur Chemie ; Volume 137, Issue 12 , 2006 , Pages 1591-1595 ; 00269247 (ISSN) Dekamin, M. G ; Moghaddam, F. M ; Saeidian, H ; Mallakpour, S ; Sharif University of Technology
    2006
    Abstract
    Alkali metal salts of phthalimide-N-oxyl, including Li, Na, and K were prepared and applied as novel selective catalysts to promote the cyclotrimerization of aryl and alkyl isocyanates. This paper is addressing these salts as a new class of organic nucleophilic catalysts. © Springer-Verlag 2006  

    In situ generation of highly active bis(N-heterocyclic)carbene palladium as an efficient catalyst in direct S-arylation of methylphenyl sulfoxide and the Heck reaction: Ligand steric effects in product selectivity

    , Article Applied Organometallic Chemistry ; 2016 ; 02682605 (ISSN) Bagherzadeh, M ; Mousavi, N ; Jamali, S ; Sharif University of Technology
    John Wiley and Sons Ltd 
    Abstract
    The use of 1,3-bis(N-heterocyclic)carbene ligands with different alkyl wingtip groups (alkyl = methyl, isopropyl and tert-butyl) is an effective method for the palladium-catalysed direct S-arylation of methylphenyl sulfoxide and C-C coupling of various of aryl halides with alkenes. The reactions proceed in moderate to good yields. Interestingly, it is shown experimentally that, by using bulkier bidentate N-heterocyclic carbene ligands, more selective catalytic systems towards cis products in Heck coupling reactions can be achieved  

    In situ generation of highly active bis(N-heterocyclic)carbene palladium as an efficient catalyst in direct S-arylation of methylphenyl sulfoxide and the Heck reaction: Ligand steric effects in product selectivity

    , Article Applied Organometallic Chemistry ; Volume 31, Issue 8 , 2017 ; 02682605 (ISSN) Bagherzadeh, M ; Mousavi, N. A ; Jamali, S ; Sharif University of Technology
    John Wiley and Sons Ltd  2017
    Abstract
    The use of 1,3-bis(N-heterocyclic)carbene ligands with different alkyl wingtip groups (alkyl = methyl, isopropyl and tert-butyl) is an effective method for the palladium-catalysed direct S-arylation of methylphenyl sulfoxide and C–C coupling of various of aryl halides with alkenes. The reactions proceed in moderate to good yields. Interestingly, it is shown experimentally that, by using bulkier bidentate N-heterocyclic carbene ligands, more selective catalytic systems towards cis products in Heck coupling reactions can be achieved. Copyright © 2016 John Wiley & Sons, Ltd  

    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) Ziyaei Halimehjani, A ; Alaei, M. A ; Soleymani Movahed, F ; Jomeh, N ; Saidi, M. R ; Sharif University of Technology
    Taylor and Francis Ltd 
    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  

    A simple and efficient method for synthesis of isocyanurates catalyzed by potassium phthalimide under solvent-free conditions

    , Article Letters in Organic Chemistry ; Volume 2, Issue 8 , 2005 , Pages 734-738 ; 15701786 (ISSN) Moghaddam, F. M ; Dekamin, M. G ; Koozehgari, G. R ; Sharif University of Technology
    2005
    Abstract
    The catalytic activity of potassium salts of phthalimide (PPI) and succinimide (PSI), as organonucleophilic catalysts, has been investigated for the cyclotrimerization of isocyanates under solvent-free conditions. PPI showed better catalytic activity in comparison with PSI. Diverse and challenging isocyanates afforded the respective symmetrical isocyanurates in good to quantitative yields in an atom economic reaction without any phase transfer catalyst. © 2005 Bentham Science Publishers Ltd  

    New Methods for the Synthesis of N,S‑Heterocycles and Dithiocarbamates Using Amine Derivatives and CS2

    , Ph.D. Dissertation Sharif University of Technology Goudarzi, Mehri (Author) ; Matloubi Moghaddam, Firouz (Supervisor)
    Abstract
    In the first section, a novel and efficient multicomponent reaction for the synthesis of polysubstituted pyrrolidine derivatives is described under catalyst-free conditions using unltrasonic irradiation. The reactions were performed via a one-pot four-component condensation of secondary amines, carbon disulfide, isocyanides, and gem-dicyano olefins at room temperature to afford polysubstituted pyrrolidines diastereoselectively in 56-96% yields. This is the first report of Mumm-type rearrangement with dithiocarbamates followed by intramolecular cyclization which lead to the preparation of the key structure of pyrrolidine.In the second section, an efficient and unprecedented green protocol... 

    Phytochemical and 2DNMR Investigation of Iranian Endemic Plants and Synthesis of Fused Polycyclic Heterocycles

    , Ph.D. Dissertation Sharif University of Technology Taheri, Salman (Author) ; Matloubi Moghaddam, Firouz (Supervisor) ; Tafazzoli, Mohsen (Supervisor) ; Amin, Gholamreza (Co-Advisor)
    Abstract
    Members of Centaurea species are common traditional medicines throughout the world. For this reason medicinal plants are the targets of intense Phytochemical studies. In this research we have investigated Centautea Golestanica which are members of this genus and endemic of Iran. In this research, One Flavonoid, two Sesquiterpenelactones and two triterpenoides were elucidated by advanced spectroscopic techniques such as IR, MS, 1H NMR, 13C NMR and 2D NMR. In continuation of this research, we have reported new and efficient methods for the synthesis of hitherto unknown indole-annulated pentacyclic indolylhydroisoquino lines and naphthooxazocines via tandem dinucleophilic addition of... 

    Synthesis and Characterization of Some Heterocyclic Compounds Containing Nitrogen and Sulfur Atoms Via Vilsmeier-haack Intermediate

    , M.Sc. Thesis Sharif University of Technology Ziadkhani, Ainaz (Author) ; Matloubi Moghaddam, Firouz (Supervisor)
    Abstract
    Heterocyclic compounds participate in a wide range of reactions, and a large number of them are known. These compounds differ in size and number of rings, type and number of heteroatoms and position of heteroatoms. In the meantime, nitrogen-containing heterocyclic compounds have been widely used in the pharmaceutical and agricultural industries due to their high biological activity. Thioxindole, a cyclic thioamide compound, has been recognized as a biologically active compound and its importance and impact in the development of chemistry are growing. In this thesis, 2-chloroquinoline-3-carbaldehyde is synthesized on acetanilide via Vilsmeier-Haack reaction, a classical reaction in organic... 

    The Use of Dithiocarbamate and Rhodanines For The Synthesis Of Sulfur-Containing Heterocyclic Compounds

    , M.Sc. Thesis Sharif University of Technology Yazdani Motlagh, Aida (Author) ; Matloubi Moghaddam, Firouz (Supervisor) ; Mahmoodi Hashemi, Mohammed (Supervisor)
    Abstract
    Nowadays, heterocycle compounds containing sulfur have become very important in various industries, especially the pharmaceutical industry; Therefore, these two projects aim to provide better and more efficient ways to synthesize these types of compounds. In the first project, we developed an efficient one-pot, four-component procedure for the synthesis of 2,6-diamino-4-Aryl-4H-Thiopyran-3,5-dicarbonitrile derivatives via a reaction between primary amines, carbon disulfide, malononitrile, and benzylidenemalononitrile in the presence of magnetic NH2.MIL-101(Fe)/ED as a basic metal-organic framework catalyst. Magnetic NH2.MIL-101(Fe)/ED was synthesized through anchoring FeCl3 on CoFe2O4... 

    Facile synthesis of thiochromeno[2,3-b]indol-11(6H)-ones and pyrido[3′,2′:5,6]thiopyrano[2,3-b]indol-5(10H)-ones

    , Article Tetrahedron Letters ; Volume 54, Issue 37 , 2013 , Pages 5018-5021 ; 00404039 (ISSN) Kiamehr, M ; Moghaddam, F. M ; Semeniuchenko, V ; Villinger, A ; Langer, P ; Iaroshenko, V. O ; Sharif University of Technology
    2013
    Abstract
    Indole-2(3H)thiones were cyclized under the action of 2-fluorobenzoyl chlorides to give thiochromeno[2,3-b]indol-11(6H)-ones or under the action of 2-chloronicotinoyl chlorides to give pyrido[3′,2′:5,6]thiopyrano[2, 3-b]indol-5(10H)-ones. The reaction of cyclization proceeds regioselectively in DMF and does not require transition metals for completion. Obtained heterocycles are isosteric analogues of various tetracyclic indole derived alkaloids  

    Pyridinium salts - Versatile reagents for the regioselective synthesis of functionalized thiazocino[2,3-b]indoles by tandem dinucleophilic reactions of thiooxindoles

    , Article Tetrahedron ; Volume 68, Issue 47 , 2012 , Pages 9685-9693 ; 00404020 (ISSN) Kiamehr, M ; Moghaddam, F. M ; Gormay, P. V ; Semeniuchenko, V ; Villinger, A ; Langer, P ; Iaroshenko, V. O ; Sharif University of Technology
    2012
    Abstract
    The reaction of thiooxindoles with various 2- and 3-substituted pyridinium salts afforded a variety of functionalized thiazocinoindoles. The products have been prepared in good to excellent yields by regioselective dinucleophilic C/S-cyclocondensation of thiooxindoles with pyridinium salts  

    Organoplatinum(ii) complexes containing chelating or bridging bis(N-heterocyclic carbene) ligands: Formation of a platinum(ii) carbonate complex by aerial CO2 fixation

    , Article Dalton Transactions ; Volume 40, Issue 37 , Jun , 2011 , Pages 9362-9365 ; 14779226 (ISSN) Jamali, S ; Milić, D ; Kia, R ; Mazloomi, Z ; Abdolahi, H ; Sharif University of Technology
    2011
    Abstract
    The preparation of two new bis(N-heterocyclic carbene) platinum(ii) complexes, in which NHC rings are joined by a CH2 linker group, is described. While, the chelate complex [PtMe2(bis-NHC1)], 1, was formed with large tert-butyl wingtips, the iso-propyl N-substituent analogue favors formation of the cluster complex [Pt2Me4(μ- SMe2)(μ-bis-NHC2)]2(μ-Ag2Br2), 2, in which two binuclear platinum(ii) complexes are linked together by an Ag2Br2 unit. The chelating platinum complex 1 undergoes aerial CO2 fixation and forms platinum(ii) carbonate complex [Pt(CO3)(bis-NHC1)], 3  

    On water: A practical and efficient synthesis of benzoheterocycle derivatives catalyzed by nanocrystalline copper(II) oxide

    , Article Synthetic Communications ; Volume 40, Issue 4 , 2010 , Pages 607-614 ; 00397911 (ISSN) Sadjadi, S ; Hekmatshoar, R ; Ahmadi, S. J ; Hosseinpour, M ; Outokesh, M ; Sharif University of Technology
    Abstract
    Recyclable CuO nanoparticles provide an efficient, economic, and novel method for the synthesis of quinoxaline, benzoxazine, and benzothiazine. This method provides a wide range of substrate applicability, avoids the use of organic solvents, and gives benzoheterocycles in satisfactory yields  

    Comparative studies of some heterocyclic compounds as corrosion inhibitors of copper in phosphoric acid media

    , Article Chemical Engineering Communications ; Volume 197, Issue 10 , 2010 , Pages 1303-1314 ; 00986445 (ISSN) Lashgari, M ; Arshadi, M. R ; Biglar, M ; Sharif University of Technology
    2010
    Abstract
    Corrosion inhibition properties of some heterocyclic compounds (3-mercapto 1,2,4 triazole, benzotriazole, thiophene, and tetra hydro-thiophene) in Cu/H3PO4 medium were investigated theoretically and experimentally via cluster/polarized continuum and gravimetric approaches. Second-order Møller-Plesset perturbation and density functional theories were applied, and the electronic chemical potential, molecular softness, and extent of charge transfer were determined for inhibitor molecules at the metal/solution interface. Good correlations were observed for both theories between the calculated quantities and experimental data. To reveal the quality of metal-inhibitor interactions, comprehensive... 

    Synthesis and Characterization of some Heterocyclic Compounds Containing Nitrogen Using Oxindole Intermediate Skeleton

    , Ph.D. Dissertation Sharif University of Technology Moafi, Atiyeh (Author) ; Matloubi Moghadam, Firouz (Supervisor)
    Abstract
    In the first part of this thesis provided an efficient and easy method for the synthesis of 3-alkylidin-2-oxindoles containing tetrahydropyrazine structure in the absence of catalysts under green conditions. The oxindole unit represents an important structural motif found in natural products and biologically relevant compounds. On the other hand, pyrazines are important and well-known compounds found in nature and many medicinal compounds. According to the aforementioned, it seems that the oxindole compounds containing the pyrazine rings exhibit high biological activity.In the second chapter of this thesis, an efficient study to synthesize thiopyrano [2,3-b] quinoline containing indole... 

    The advantage of spectrophotometric measurement for size-selective complexing of Cu(II) with O2N2-azacrown ligands

    , Article Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy ; Volume 139 , March , 2015 , Pages 286-289 ; 13861425 (ISSN) Ghanbari, B ; Gholamnezhad, P ; Sharif University of Technology
    Elsevier  2015
    Abstract
    A comparative investigation of the interaction of Cu(II) with a series of 15- to 19-membered mixed-donor dibenzo-substituted macrocyclic ligands, each incorporating an O2N2-donor set, has been carried out using UV-Visible studies in methanol. Although a ring size effect has been reported for a related series of Ni(II) complexes, no such metal ion discrimination has been reported for Cu(II) in terms of its binding constants with 14- to 17-membered macrocycles. Employing Job's method of continuous variation established 1:1 stoichiometry for the interaction between Cu(II) and 1-5. From UV-Visible studies applying the Benesi-Hildebrand equation, the binding constants (K) of Cu(II) with 1-5 were...