Loading...
Search for:
indole
0.006 seconds
Total 31 records
Clean and facile condensations reaction of indoles and carbonyl compounds under solvent-free conditions
, Article Letters in Organic Chemistry ; Volume 3, Issue 2 , 2006 , Pages 161-164 ; 15701786 (ISSN) ; Azizi, N ; Saidi, M. R ; Sharif University of Technology
2006
Abstract
A simple, rapid, atom economy and highly efficient green protocol has been developed for the reactions of indole with carbonyl compounds under solvent- free conditions. The attractive features of these procedures are the mild reaction conditions, high conversions, cleaner reaction profiles, inexpensive and environmentally friendly lithium perchlorate and short reaction times. © 2006 Bentham Science Publishers Ltd
Synthesis of Bromonitroalkenes and their Applications as Electrophile in the Reaction with Indoles
, M.Sc. Thesis Sharif University of Technology ; Mahmoodi Hashemi, Mohammad (Supervisor) ; Ziyaei Halimehjani, Azim (Co-Advisor)
Abstract
In this work Nitroolefins were made by aromatic aldehydes consisting of electron withdrawing and electron donor groups. Afterward β-Bromo-β-nitrostyrenes were produced from interaction between nitroolefins and brom, at suitable temperature. After providing ingredients, micheal reaction (Friedel-crafts Pseudo-alkylation) between nitroolefins and various nucleophiles such as indoles was investigated. Finally desired micheal products were achived with high efficiency
Catalyst-Free three-component synthesis of spirobenzimidazolidines bearing an indole scaffold
, Article Synlett ; Volume 29, Issue 17 , 2018 , Pages 2301-2305 ; 09365214 (ISSN) ; Moafi, A ; Zamani, Z ; Daneshfar, M ; Sharif University of Technology
Georg Thieme Verlag
2018
Abstract
An efficient catalyst-free one-pot three-component reaction was developed for the synthesis of a new family of N- A nd S-containing spirocyclic compounds. Various derivatives of spirobenzimidazolidine containing an indole scaffold were synthesized for the first time in a modestly toxic solvent and under mild reaction conditions. The reaction times were of the order of several minutes, and all the products were obtained in moderate to high yields (overall yields 58-80%). © Georg Thieme Verlag Stuttgart New York
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
2005
Abstract
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
The stereoselective synthesis of tetrahydrothiopyrano[2,3-b]indole skeletons via tandem reaction of indoline-2-thiones to Baylis-Hillman adduct acetates
, Article Tetrahedron ; Volume 69, Issue 38 , September , 2013 , Pages 8169-8173 ; 00404020 (ISSN) ; Foroushani, B. K ; Sobhani, M ; Masoud, N ; Khodabakhshi, M. R ; Weng, N. S ; Sharif University of Technology
2013
Abstract
Indoline-2-thiones (5) were applied as 1,3-dinucleophiles in a tandem reaction with Baylis-Hillman adduct acetates (4) to give novel tetrahydrothiopyrano[2,3-b]indole skeletons (6). The effect of different solvents, bases, and catalysts on the yields and stereochemical outcome was studied in detail. The results indicated that acetonitrile as solvent and K 2CO3 as base, under reflux conditions, were the optimum conditions. Products 6a-6l were obtained in high diastereoselectivity and yield (up to 94%)
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) ; 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) ; 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
A convenient synthesis of 3-formyl-2-thioacetamide-indole derivatives via the one-pot reaction of indolin-2-thiones, isocyanides and chloroacetylchloride
, Article Tetrahedron Letters ; Volume 56, Issue 52 , 2015 , Pages 7190-7192 ; 00404039 (ISSN) ; Matloubi Moghaddamb, F ; Sadeghi Erami, M ; Sharif University of Technology
Abstract
An efficient method has been developed to construct 3-formyl-2-thioacetamide-indoles via a one-pot, two-step procedure involving condensation of isocyanides with indolin-2-thiones to give a 3-aminomethylene-indolin-2-thione intermediate, followed by regioselective reaction with chloroacetylchloride and subsequent hydrolysis
A Facile and Efficient Route for the Synthesis of Thiopyranoquinolines-Fused Indole Moiety Using 2-Chloroquinoline-3-carbaldehydes
, Article ChemistrySelect ; Volume 4, Issue 40 , 2019 , Pages 11683-11686 ; 23656549 (ISSN) ; Moafi, A ; Ziadkhani, A ; Daneshfar, M ; Razaghdoost, N ; Sharif University of Technology
Wiley-Blackwell
2019
Abstract
The reaction of 2-chloroquinoline-3-carbaldehydes with indoline-2-thione in ethanol provides a series of novel indolo[3′,2′:5,6]thiopyrano[2,3-b]quinoline derivatives. The desired products were obtained in short reaction time and high yields (69-93%) under mild reaction conditions. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
KF/Al2O3 mediated aza-Michael addition of indoles to electron-deficient olefins
, 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
2006
Abstract
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
Influence of the water molecules (n 5 1-6) on the interaction between Li +, Na +, K + cations and indole molecule as tryptophan amino acid residue
, Article Structural Chemistry ; Volume 23, Issue 3 , 2012 , Pages 857-865 ; 10400400 (ISSN) ; Nasiri, M ; Fattahi, A ; Vafaeezadeh, M ; Sharif University of Technology
2012
Abstract
Influence of the addition of water molecules (n = 1-6) on the interaction energy between Li +, Na +, K + cations and indole molecule as tryptophan amino acid residue is considered at MP2(FULL)/6-311++G(d, p)//B3LYP/6-311++G(d,p) levels of theory. The calculations suggest that the size of cation and the number of water molecules are two important factors that affect the interaction energy between the hydrated metal cation and indole molecule. The strength of cation-π interactions get substantially reduced when the metal ion is solvated or the size of metal cation increases. Quantum theory of atoms in molecules analysis of cation-π interaction indicates that there is a correlation between the...
Generation of arylnitrenium ions by nitro-reduction and gas-phase synthesis of N-heterocycles
, Article Journal of the American Society for Mass Spectrometry ; Volume 15, Issue 11 , 2004 , Pages 1675-1688 ; 10440305 (ISSN) ; Chen, H ; Cooks, R. G ; Bagheri, H ; Sharif University of Technology
2004
Abstract
Nitro-reduction by the vinyl halide radical cation CH 2 = CH-X +· (X = Cl or Br) converts nitroaromatics into arylnitrenium ions, significant intermediates in carcinogenesis, and the present study reports on the scope and regioselectivity of this versatile reaction. The reaction is general for different kinds of substituted nitroaromatics; para/meta substitutents have little effect on the reaction while ortho substitutents result in low yields of arylnitrenium ions. The phenylnitrenium ion PhNH + can be generated by chemical ionization (CI) of nitrobenzene using 1,2-dichloroethane as the reagent gas or by atmospheric pressure chemical ionization (APCI) of 1,2-dichloroethane solution doped...
Synthesis of novel pentacyclic thiopyrano indole-annulated benzo-δ-sultone derivatives via a domino Knoevenagel-hetero-Diels-Alder reaction in water
, Article Tetrahedron Letters ; Volume 54, Issue 21 , 2013 , Pages 2685-2689 ; 00404039 (ISSN) ; Khodabakhshi, M. R ; Kiamehr, M ; Ghahremannejad, Z ; Sharif University of Technology
2013
Abstract
An efficient synthesis of novel pentacyclic thiopyrano indole-annulated benzo-δ-sultone derivatives is achieved via intramolecular domino Knoevenagel-hetero-Diels-Alder reaction of 2-formylphenyl (E)-2-phenylethenyl sulfonates and indoline-2-thiones in aqueous medium. The products are formed in good yields with high regio- and stereoselectivity
New entry to bridged pentacyclic indolyltetrahydroisoquinoline skeleton via tandem s-alkylation and intramolecular C-Alkylation
, Article Synlett ; Issue 1 , 2010 , Pages 123-127 ; 09365214 (ISSN) ; Taheri, S ; Mirjafary, Z ; Saeidian, H ; Sharif University of Technology
2010
Abstract
An efficient, single-step synthesis of hitherto unknown indole-annulated pentacyclic indolylhydroisoquinolines via tandem S-alkylation and intramolecular C-alkylation of indolin-2-thiones with N-alkylisoquinolinium salts is reported. This new approach provides a powerful entry into polycyclic structures containing nitrogen and sulfur related to alkaloids
Synthesis of novel polycyclic indole-annulated thiopyranocoumarin derivatives via domino Knoevenagel-hetero-Diels-Alder reaction in aqueous media
, Article Helvetica Chimica Acta ; Volume 93, Issue 5 , 2010 , Pages 964-973 ; 0018019X (ISSN) ; Kiamehr, M ; Taheri, S ; Mirjafary, Z ; Sharif University of Technology
Abstract
An efficient synthesis of polycyclic indole derivatives is achieved via domino Knoevenagel - hetero-Diels - Alder reaction of O-acrylated salicylaldehyde derivatives with dihydroindole-2-thiones in H2O as solvent. The products are formed in good-to-excellent yields with high regio- and stereoselectivity
One-pot synthesis of dispiro[oxindole-3,3′-pyrrolidines] by three-component [3+2] cycloadditions of in situ-generated azomethine ylides with 3-benzylidene-2,3-dihydro-1H-indol-2-ones
, Article Helvetica Chimica Acta ; Volume 96, Issue 11 , 2013 , Pages 2103-2114 ; 0018019X (ISSN) ; Kiamehr, M ; Reza Khodabakhshi, M ; Jebeli Javan, M ; Fathi, S ; Villinger, A ; Iaroshenko, V. O ; Langer, P ; Sharif University of Technology
2013
Abstract
An efficient one-pot, three-component synthesis of novel dispiro[oxindole-3,3′-pyrrolidines] by 1,3-dipolar cycloaddition of azomethine ylides, in situ generated by reaction of 1,2-diones with sarcosine and subsequent decarboxylation, with a series of (E)-3-benzylidene-2,3-dihydro- 1H-indol-2-ones is reported. Molecular complexity is generated in only one synthetic step. All reactions proceed with excellent regioselectivity and in good-to-excellent yields. The workup is easy, the reaction times are short, and no catalyst is required. © 2013 Verlag Helvetica Chimica Acta AG, Zürich
Design a New Magnetic Nanocatalyst Based on Palladium (II) and Its Application for the Selective Oxidation Reaction of Alcohol to Aldehyde
, M.Sc. Thesis Sharif University of Technology ; Matloubi Moghaddam, Firouz (Supervisor) ; Sajadi, Ali Akbar (Supervisor)
Abstract
In the first chapter of the thesis the synthesis of indolylsulfanyl acetamide derivatives using thio-oxindoles has been reported. The properties of this reaction are, one-pot, without using catalysts, acetonitrile solvent and the raw material is available. This reaction has high yield and seperation products is done using column chromatography. Indole derivatives has various medicinal and biological properties and synthetic products in this project has indole ring, aldehyde and amide functional groups. In the second chapter of the thesis, a new magnetic nanocatalyst has been designed. The magnetic nanoparticles were coated with triazole ligand and then palladium (II) ion was loaded onto the...
Synthesis and Characterization of some Nitrogen Containing Heterocyclic Compounds Using Synthetic Intermediat of Isatin Analogues
, M.Sc. Thesis Sharif University of Technology ; Matloubi Moghaddam, Firouz (Supervisor)
Abstract
An efficient catalyst-free one-pot three-component reaction was developed for the synthesis of a new family of N- and S-containing spirocyclic compounds.Various derivatives of spirobenzimidazolidine containing an indole scaffold were synthesized for the first time in a modestly toxic solvent and under mild reaction conditions. The reaction times were of the order of several minutes, and all the products were obtained in moderate to high yields (overall yields 58–80%)
Facile entry to polycyclic indolylhydroquinoline skeletons via tandem C-alkylation and intramolecular S-alkylation
, Article Tetrahedron ; Volume 66, Issue 1 , 2010 , Pages 134-138 ; 00404020 (ISSN) ; Mirjafary, Z ; Saeidian, H ; Taheri, S ; Doulabi, M ; Kiamehr, M ; Sharif University of Technology
Abstract
An efficient, single step synthesis of hitherto unknown indole-annulated pentacyclic indolylhydroquinolines via tandem C-alkylation and intramolecular S-alkylation of indolin-2-thiones with N-alkylquinolinium salts in excellent yields (83-95%) is reported. This facile approach provides a powerful entry into polycyclic structures containing nitrogen and sulfur related to alkaloids. The structure of the product was determined by Röntgen crystal structure analysis
Identification of an aspidospermine derivative from borage extract as an anti-amyloid compound: A possible link between protein aggregation and antimalarial drugs
, Article Phytochemistry ; Volume 140 , 2017 , Pages 134-140 ; 00319422 (ISSN) ; Ashrafian, H ; Sharif University of Technology
Elsevier Ltd
2017
Abstract
A number of human diseases, including Alzheimer's and Parkinson's have been linked to amyloid formation. To search for an anti-amyloidogenic product, alkaloid enriched extract from borage leaves was examined for anti-amyloidogenic activity using Hen Egg White Lysozyme (HEWL) as a model protein. After isolation of the plant extract using rHPLC, only one fraction indicated a significant bioactivity. TEM analysis confirmed a remarkable reduction of amyloid fibrils in the presence of the bioactive fraction. To identify the effective substance in the fraction, mass spectrometry, FTIR, and NMR were performed. Our analyses determined that the bioactive compound as...