Sharif Digital Repository

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  

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  

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 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  

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  

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... 

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  

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... 

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... 

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  

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... 

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... 

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... 

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