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Aminoalkylation with aldehydes mediated by solid lithium perchlorate
, Article Monatshefte fur Chemie ; Volume 135, Issue 3 , 2004 , Pages 309-312 ; 00269247 (ISSN) ; Nazari, M ; Sharif University of Technology
2004
Abstract
The solid LiClO4-mediated one-pot reaction of aldehydes with secondary amines and C nucleophiles afforded the corresponding aminoalkylation products in high yields. Unlike the previous reported procedure, the aminoalkylation of aldehyde was achieved in the presence of only 0.5 equivalents of solid lithium perchlorate in dichloromethane as the solvent with good to high yields at room temperature. © Springer-Verlag 2003
Lithium perchlorate mediated three-component preparation of primaryaminoesters
, Article Molecules ; Volume 7, Issue 1 , 2002 , Pages 72-74 ; 14203049 (ISSN) ; Azizi, N ; Sharif University of Technology
Molecular Diversity Preservation International
2002
Abstract
A three-component reaction between an aldehyde, metallated hexamethyldisilazane and a functionalized organozinc compound proceeded smoothly in the presence of LiClO4 in diethyl ether to afford primary amino esters in good yields
Surfactant-Like brønsted acidic ionic liquid as an efficient catalyst for selective mannich reaction and biodiesel production in water
, Article Journal of the Iranian Chemical Society ; Volume 14, Issue 4 , 2017 , Pages 907-914 ; 1735207X (ISSN) ; Karbalaie Reza, M ; Mahmoodi Hashemi, M ; Qasempour Soleimany, K ; Sharif University of Technology
Springer Verlag
2017
Abstract
Abstract: The current study deals with the applications of a surfactant-like Brønsted acidic ionic liquid (IL) 1-dodecyl-3-methylimidazolium hydrogen sulfate ([DMIm]HSO4) for Mannich reaction at room temperature. The reaction was efficiently preceded in water as solvent without using any harmful and expensive organic additives. Our findings showed that the reaction is selective for cyclohexanone and no Mannich product was observed when cyclopentanone was used as starting material. Density functional theory (DFT) calculations were performed to provide an evidence about the nature of reactivity of the cyclohexanone/cyclopentanone. The activity of the catalyst was also tested for biodiesel...
Lithium perchlorate assisted one-pot three-component aminoalkylation of electron-rich aromatic compounds
, Article Tetrahedron Letters ; Volume 42, Issue 45 , 2001 , Pages 8111-8113 ; 00404039 (ISSN) ; Azizi, N ; Naimi Jamal, M.Reza ; Sharif University of Technology
2001
Abstract
A one-pot, three-component, Mannich reaction of electron-rich aromatic compounds with in situ prepared iminium salts in 5 M ethereal lithium perchlorate gives good yields of aminoalkylated products at room temperature. © 2001 Elsevier Science Ltd. All rights reserved
Investigation of One-Pot Three-Component Reaction of Naphthalenediols with Formaldehyde and Amines under Catalyst-free Conditions
, M.Sc. Thesis Sharif University of Technology ; Saidi, Mohammad Reza (Supervisor) ; Ziyaei Halimehjani, Azim (Supervisor)
Abstract
In this study, a catalyst-free Mannich reaction is applied for synthesis of 1,3-oxazines as an important class of biologically active compounds. In order to consider environmental application a mixture of water and ethanol is selected as a solvent for the reaction of 2,7-dihydroxynaphthalene with formaldehyde and an amine. Primary consideration of substitution effect on the reaction revealed that aniline and its derivatives with electron-donating substituent and halogens, cause higher yield. Aliphatic amines are not good substrate for this reaction with the exception of benzyl amine
Synthesis and Application of Acidic and Hydrophobic Ionic Liquids in Mannich Reaction and Esterification of Fatty Acids
, M.Sc. Thesis Sharif University of Technology ; Mahmoodi Hashemi, Mohammed (Supervisor)
Abstract
The current study deals with application of a surfactant-like Brønsted acidic ionic liquid (IL) 1-dodecyl-3-methylimidazolium hydrogensulfate (catalys 1) for Mannich reaction at room temperature. The reaction has been efficiently proceeds in water as solvent without using any harmful and expensive organic additives. Our observation has been shown that the reaction is selective for cyclohexanone and no product was observed by using cyclopentanone at room temperature. Density functional theory (DFT) calculations were performed to provide evidence about the nature of reactivity of the cyclohexanone/cyclopentanone. The activity of the catalyst 2 (1-dodecyl-2,3-dimethylimidazolium...
Synthesis of β-Amino Ketones Using Titania Based on Solid Acid as A Catalyst
, M.Sc. Thesis Sharif University of Technology ; Mahmoudi Hashemi, Mohammad (Supervisor)
Abstract
Enanthioselective synthesis of biological molecules are so important in synthetic chemistry, and because of their biological activities, β-amino carbonyl compounds have earned so much attention in this area of chemistry. Mannich reaction is a classical method for synthesis of these molecules. The Mannich reaction is a three-component reaction between an enolizable CH-acidic carbonyl compound, an amine, and an aldehyde producing β-amino carbonyl compounds. But acidic or basic difficult circumstances, long reaction time, low yield and enantioselectivity, are the drawbacks of classical methods. In this project, we used titania-based solid acid as an enantioselective catalyst to overcome these...
LiClO4-accelerated three-component Mannich-type reaction of diethyl malonate with imines: An efficient synthesis of β-amino esters under solvent-free conditions
, Article Synthetic Communications ; Volume 38, Issue 22 , 2008 , Pages 4036-4044 ; 00397911 (ISSN) ; Saidi, M. R ; Sharif University of Technology
2008
Abstract
LiClO4 is used as catalyst for direct Mannich-type reaction of aryl aldehydes, aryl amines, and diethyl malonic ester under solvent-free conditions. This three-component reaction afforded the corresponding β-amino esters in good yields with simple and environmentally benign procedure. Copyright © Taylor & Francis Group, LLC
Investigating One-pot Three Component Synthesis of ß-Amino Carbonyl Compounds Exploiting Hydrolases: Protein Splicing Enzyme and N-Acetylmuramide Glycanhydrolase
, M.Sc. Thesis Sharif University of Technology ; Kalhor, Hamidreza (Supervisor)
Abstract
The application of biocatalysts in organic reactions refers to the use of enzymes, purified or crude, to increase the reaction rate. The usage of biocatalysts in organic reactions have many advantages, including biocompatibility, ease of separation, high yield, reusability without losing activity, high selectivity, and the use of water as the solvent. Furthermore, the carbon–carbon bond formation is one of the most important reactions in the synthesis of organic compounds, drugs, and biomolecules. Using enzymes in organic reactions can provide insightful information about the enzymes catalytic activities and paves the way for systematic investigation of their mechanisms. The enzymes...
Stereoselective synthesis ofβ-Amino ketones via direct mannich-type reaction catalyzed with SO 2- 4/TiO 2 and SO 2- 4/nano TiO 2
, Article Synthetic Communications ; Volume 39, Issue 24 , 2009 , Pages 4441-4453 ; 00397911 (ISSN) ; Eftekhari Sis, B ; Mahmodi Hashemi, M ; Farmad, F ; Sharif University of Technology
2009
Abstract
At room temperature, SO 2- 4/nano-TiO 2 efficiently catalyze the direct Mannich-type reaction of varieties of in situ-generated aldimines using aldehydes and anilines with ketones in a three-component reaction under solvent-free conditions. The reaction proceeds rapidly and affords the correspondingβ-amino ketones in good to high yields with good to excellent stereoselectivity. The catalyst can be recycled for subsequent reactions without any appreciable loss of efficiency
Highly efficient one-pot three-component mannich reaction under solvent-free conditions
, Article Scientia Iranica ; Volume 16, Issue 2 C , 2009 , Pages 94-98 ; 10263098 (ISSN) ; Ebrahimi, F ; Saidi, M. R ; Sharif University of Technology
2009
Abstract
A mild and practically-convenient one-pot procedure for the direct Mannich reaction has been developed using a condensation of amines, aldehydes and unmodified ketones under solvent free conditions in the presence of Znl 2 with good to excellent yields. The present methodology offers several advantages, such as excellent yields, simple procedures, short reaction times and milder conditions with very small amounts of catalyst. Furthermore, it is the first time that the catalytic activity of several catalysts under solvent free conditions has been studied. It was found that both the diastereoselectivity and the rate of reaction were improved with various Lewis acids and metal oxides. However,...