Industrial and Engineering Chemistry Research (15205045)61(10)pp. 3694-3703
A novel porous organic polymer with thioether-functionalized succinimide (TS-POP) through radical copolymerization as a facile, metal-free, and cost-effective strategy for Hg2+ removal from aqueous solution is presented. Fourier transform infrared (FT-IR) spectroscopy and powder X-ray diffraction (XRD) were used to confirm the structure, while morphology, porosity, and physicochemical properties were determined using scanning electron microscopy (SEM), N2 adsorption/desorption isotherm, and thermogravimetric analysis. Due to the presence of thioether functional groups in the polymer backbone together with the hierarchical porosity, TS-POP adsorbed Hg2+ ions with an excellent uptake capacity (833 mg g-1) and exhibited rapid adsorption kinetics. The adsorption process of Hg2+ ions over TS-POP is better described with Langmuir and pseudo-second-order models. Also, TS-POP showed very good selectivity for Hg2+ uptake among various examined metal ions (Hg2+, Cd2+, Zn2+, Ni2+, Fe3+, Ca2+, Mg2+, Ba2+, and Na+) from aqueous media. The extraordinary physicochemical stability, hierarchical porosity, possibility of large-scale preparation, superior selectivity, and exceptional recyclability make TS-POP a perfect candidate for Hg2+ removal from aqueous solutions in practical applications. © 2022 American Chemical Society.
RSC Advances (20462069)11(6)pp. 3655-3665
A novel porous organic polymer (denoted by Q-POP) was successfully fabricated by free-radical copolymerization of allyl-substituted 2,3-di(2-hydroxyphenyl)1,2-dihydroquinoxaline, and divinylbenzene under solvothermal conditions and used as a new platform for immobilization of copper nanoparticles. The CuNPs@Q-POP nanocatalyst was prepared via incorporating of Cu(NO3)2 into the polymeric network, followed by the reduction of Cu2+ ion with hydrazine hydrate. The obtained materials were characterized through FT-IR, XRD, N2 adsorption-desorption isotherms, ICP, TGA, SEM, HR-TEM, EDX, and the single-crystal X-ray crystallography. The results displayed that Q-POP and CuNPs@Q-POP possessed high surface area, hierarchical porosity, and excellent thermal and chemical stability. The as-synthesized catalyst was utilized for the Ullmann C-N coupling reaction of aromatic amines and different aryl halides to prepare various diarylamine derivatives. All types of aryl halides (except aryl fluorides) were screened in the Ullmann C-N coupling reaction with aromatic amines to produce diaryl amines in good to excellent yields (50-98%), and it turned out that aryl iodides have the best results. Besides, due to the strong interactions between CuNPs, N, and O-atoms of quinoxaline moiety existing in the polymeric framework, the copper leaching from the support was not observed. Furthermore, the catalyst was recycled and reused for five consecutive runs without significant activity loss. © The Royal Society of Chemistry.
Molecular Catalysis (24688231)504
A quinoxaline-based porous organic polymer (Q-POP) as a mesoporous organic copolymer was developed as a new platform for the immobilization of CuNPs and copper nanocrystals. The prepared materials were characterized by FT-IR, XRD, N2 adsorption-desorption isotherms, ICP, TGA, SEM, HR-TEM, EDX, and single-crystal X-ray crystallography. The obtained catalyst presented extraordinary catalytic activity towards Ullmann C–O coupling reactions with high surface area, hierarchical porosity, and excellent thermal and chemical stability. Due to its high porosity, and synergistic effect of copper nanocrystals incorporated in the polymer composite, the as-synthesized catalyst was successfully utilized for the Ullmann C–O coupling reaction of phenols and different aryl halides to prepare various diaryl ether derivatives. All types of aryl halides (except aryl fluorides) were screened in the Ullmann C–O coupling reaction with phenols to produce diaryl ethers in good to excellent yields (70–97 %), and it was found that aryl iodides have the best results. Besides, due to the strong interactions between CuNPs, N, and O-atoms of quinoxaline moiety existing in the polymeric framework, the copper leaching from the support was not observed. Furthermore, the catalyst was recycled and reused for five consecutive runs without significant activity loss. © 2021 Elsevier B.V.
Novel supramolecular gelators based on quinoline-indolin-2-one structure were synthesized. These gelators formed stable organogels in a mixture of DMSO/H2O (1:1). The scanning electron microscopy (SEM), IR and NMR spectroscopies, and rheological measurements were used to study the properties of the gels. Among the synthesized compounds, G2 was chosen as the best gelator and utilized as a naked eye chemosensor for the selective detection of Cu2+ and Hg2+ ions alongside and CN‾ ion as toxic and hazardous materials. The gelator G2 was selectively transformed into a sol state in the presence of Cu2+ ion alongside with a vivid change of color from orange to cherry red. Hg2+ ion showed a notable change in color from orange to brick red, but the gel state remained intact. The detection limit for the gelator G2 toward Cu2+and Hg2+ were 7.25 × 10−6 mol. L−1 and 4.80 × 10−6 mol. L−1 respectively. All the tested anions had no distinct effect on the gel state and/or the color of G2, while, in the presence of CN‾, although the gel state was again unchanged a drastic color change from orange to dark purple was observed. The detection limit for G2 toward CN− was 1.36 × 10−4 mol. L−1. The gelator G2 also operated simultaneously the roles of INH and OR gates in which water, Hg2+, Cu2+ ions are inputs, and the gel state and absorbance around 600 nm (color change) are outputs. © 2020 Elsevier B.V.
ChemistrySelect (23656549)5(2)pp. 886-893
Three quinoline-based Low Molecular Weight Gelators (LMWG's), containing benzimidazole and long alkyl chain moieties, with excellent gelation abilities have been designed and synthesized. The gel properties were studied by IR and NMR spectroscopies, scanning electron microscopy (SEM) and rheological measurements. The gelators showed excellent ability as efficient colorimetric and fluorescent sensors for detection of Hg2+ and Cu2+ ions in aqueous media. The supramolecular gel was selectively transformed into solution in the presence of Hg2+ ion alongside complete quenching of its fluorescence intensity. In the presence of Cu2+ ion, the gelator exhibited a significant color change from white to dark pink and its fluorescence intensity was substantially reduced in gel-gel state. Other competing ions such as Mn2+, Zn2+, Pb2+, Cd2+, Mg2+, Ni2+and Al3+, induced no change under the same conditions. The gel function as molecular logic gate was also investigated and found that, the gelators implement the functions of INH and NOT gates with water and Hg2+ ion as inputs and gel formation and fluorescence intensity as outputs. © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Mansouri, S.G.,
Zali boeini, H.,
Zomorodian, K.,
Khalvati, B.,
Pargali, R.H.,
Dehshahri, A.,
Amiri rudbari, H.,
Sahihi, M.,
Chavoshpour, Z. Arabian Journal Of Chemistry (18785352)13(1)pp. 1271-1282
A series of novel naphtho[1,2-e][1,3]oxazines bearing arylsulfonamide moiety have been synthesized via a one-pot approach and in a green reaction medium. These new naphtho[1,2-e][1,3]oxazine derivatives have been characterized by their 1H NMR, 13C NMR and the X-ray single crystallography method for compound 7a. All the newly synthesized compounds were examined for their in vitro anticancer activity against breast (MCF-7), colon (HCT116), and B-CLL (Waco3-CD5) cancers. Some of these compounds such as 7j and 7l showed remarkable activities against MCF-7 (breast) and HCT116 (colon) cancers with comparable IC50 (The half maximal inhibitory concentration) values as that of known drugs such as 5-fluorouracil (5-FU). In vitro antimicrobial activities of all compounds were also evaluated against five human pathogenic fungi strains and two bacteria (one gram positive and one gram negative). The best MICs (Minimum Inhibitory Concentrations) were found against the C. albicans. © 2017 King Saud University
Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy (13861425)207pp. 16-22
A very effective and highly sensitive fluorescent chemosensor, based on 4-hydroxycoumarin skeleton substituted by benzothiazole moiety was synthesized and investigated for the detection of zinc ion. This chemosensor displays highly selective and sensitive fluorescence enhancement to Zn2+ over other metal ions examined in solution and in biological systems. The detection limit for the fluorescent chemosensor 1 toward Zn2+ was 3.58 × 10−8 M. A simple and efficient approach was improved for the synthesis of chemosensor 1 starting from 4-hydroxycoumarin. © 2018 Elsevier B.V.
Journal Of The Iranian Chemical Society (1735207X)16(6)pp. 1139-1146
A series of 4-amino-functionalized spiropyrimidine-2-thione derivatives were simply produced by the one-pot three-component reaction of alicyclic carbonyl compounds, nitriles containing an acidic methylene, and thiourea in the presence of NaOMe in MeOH. © 2019, Iranian Chemical Society.
Majnooni, S.,
Duffield, J.,
Price, J.,
Khosropour, A.R.,
Zali boeini, H.,
Beyzavi, M.H. ACS Combinatorial Science (21568952)21(7)pp. 516-521
Several straightforward and practical processes have been established for the construction of 2-aminothiazoles, 1,3-thiazoles and 1,3-selenazoles from aryliodoazides. These strategies successfully proceed with a wide spectrum of substituted thioamides and its derivatives producing the resulting five-membered heterocycles obtained in satisfactory yields. The unique features of these protocols are operational simplicity and highly functional group tolerance, which make them convenient and practical routes for the preparation of various libraries of 2-aminothiazoles, 1,3-thiazoles, and 1,3-selenazoles. © 2019 American Chemical Society.
Soft Materials (15394468)17(2)pp. 150-158
Four glucose-based phase selective organogelators were designed and synthesized from low-cost and readily available starting materials. Our rapid acting supergelators were able to gelate a wide spectrum of solvents in mono- or biphasic systems, at very low concentration. They were shown to solidify oil spills at room temperature, in the form of a semi-dried gel, within 90 min. It was also revealed that their n-butanol gel could effectively absorb pollutant dyes from aqueous media. As novel smart materials, these gelators are potentially applicable to remove contaminants including aromatic solvents, oil spills, and toxic dyes from water resources. The gelators have been well characterized using spectroscopic, microscopic, and rheological studies. © 2019, © 2019 Taylor & Francis Group, LLC.
Majnooni, S.,
Almansaf, Z.,
Tsuji, M.,
Khosropour, A.R.,
Zali boeini, H.,
Beyzavi, M.H. Synthesis (Germany) (1437210X)51(22)pp. 4279-4283
A one-pot process for the efficient synthesis of 3,5-diaryl-1,2,4-selenadiazoles from aryl nitriles has been developed. This tandem transformation was performed in excellent yields (91-98%) via in situ selenoamidation and a subsequent oxidative dimerization reaction. This method features relatively mild reaction conditions, operational simplicity, straightforward separation of the products, and the utilization of inexpensive reagents. © 2019 Georg Thieme Verlag. All rights reserved.
Ariyaeifar, M.,
Amiri rudbari, H.,
Sahihi, M.,
Kazemi, Z.,
Abbasi kajani, A.,
Zali boeini, H.,
Kordestani, N.,
Bruno, G.,
Gharaghani, S. Journal of Molecular Structure (00222860)1161pp. 497-511
Eight enantiomerically pure halogenated Schiff base compounds were synthesized by reaction of halogenated salicylaldehydes with 3-Amino-1,2-propanediol (R or S) in water as green solvent at ambient temperature. All compounds were characterized by elemental analyses, NMR (1H and 13C), circular dichroism (CD) and FT-IR spectroscopy. FS-DNA binding studies of these compounds carried out by fluorescence quenching and UV–vis spectroscopy. The obtained results revealed that the ligands bind to DNA as: (R–ClBr) > (R–Cl2) > (R–Br2) > (R–I2) and (S–ClBr) > (S–Cl2) > (S–Br2) > (S–I2), indicating the effect of halogen on binding constant. In addition, DNA-binding constant of the S– and R-enantiomers are different from each other. The ligands can form halogen bonds with DNA that were confirmed by molecular docking. This method was also measured the bond distances and bond angles. The study of obtained data can have concluded that binding affinity of the ligands to DNA depends on strength of halogen bonds. The potential anticancer activity of ligands were also evaluated on MCF-7 and HeLa cancer cell lines by using MTT assay. The results showed that the anticancer activity and FS-DNA interaction is significantly dependent on the stereoisomers of Schiff base compounds as R-enantiomers displayed significantly higher activity than S-enantiomers. The molecular docking was also used to illustrate the specific DNA-binding of synthesized compounds and groove binding mode of DNA interaction was proposed for them. In addition, molecular docking results indicated that there are three types of bonds (H– and X-bond and hX-bond) between synthesized compounds and base pairs of DNA. © 2018 Elsevier B.V.
Dyes and Pigments (01437208)159pp. 337-344
Some novel sugar-based and multistimuli responsive supramolecular gelators, containing azobenzene moieties were synthesized and characterized through their microscopic, rheological, and spectroscopic measurements. The sol-gel behavior of these low molecular weight gelators in response to temperature, UV–Vis light irradiation, pH changes, and in the presence of various metal cations was investigated. Compounds 2b and 2d were found to be as supergelators (gelator concentration≤ 1%) in a mixture of DMF/H2O (1:1) and exhibited very good responses toward temperature, light, pH, and metal ions. Moreover, compound 2b showed selective gel-sol response toward Cu2+ among a wide variety of two and three-valent metal ions. © 2018 Elsevier Ltd
Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy (13861425)178pp. 198-202
A new isoindoline–based highly efficient turn-on fluorescent chemodosimeter S with a thioamide functionality as a binding site for selective detection of Hg2 + ion has been developed. The chemodosimeter S showed an extreme selectivity for detection of Hg2 + ion among various two and three-valent metal ions in acetonitrile/water (70/30, v/v). It was found that, in the presence of Hg2 + ion the non-fluorescent chemodosimeter S was efficiently and rapidly desulfurized to the corresponding highly fluorescent amide 1. A good linear relationship was shown between the fluorescence intensity and the concentration of Hg2 + within the range of 0–1 μM, with a detection limit of 2.03 × 10− 8 M. © 2017 Elsevier B.V.
Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy (13861425)178pp. 66-70
A highly efficient and selective fluorescent and colorimetric chemosensor based on naphthothiazole skeleton was synthesized and its colorimetric and fluorescent properties were investigated. The sensor displays a rapid and highly selective colorimetric and fluorescence response toward Hg2 + without interference with other metal ions in CH3CN/H2O mixture (50/50, v/v). The detection limit for the fluorescent chemosensor S1 toward Hg2 + was 3.42 × 10− 8 M. © 2017 Elsevier B.V.
Journal of Fluorescence (15734994)27(3)pp. 1035-1040
A fluorescent and colorimetric chemosensor for detection of cyanide ion based on a styryl quinoline derivative has been designed and synthesized. The chemosensor (E)-2-(4-mercaptostyryl)quinolin-8-ol L showed high selectivity for detection of cyanide over other anions such as F¯, Cl¯, Br¯, I¯, NO3¯, SCN¯, N3¯, ClO4¯, H2PO4¯, AcO¯, HCO3¯, SO4 2¯ and HSO4¯in aqueous solution. The chemosensor L displayed an immediate visible and fluorescence changes from nearly colorless to orange and greenish-blue to brick-red upon addition of cyanide ion respectively. It is more likely, these distinct changes can be attributed to hydrogen bonding interaction between phenol group and cyanide anion leading to a 1:1 binding stoichiometry following with deprotonation of phenol group. The detection limit for chemosensor L toward CN¯ was 2.73× 10−8 M. Thus, the chemosensor can be used efficiently and selectively for detection and monitoring of small amounts of cyanide ion in aqueous media. © 2017, Springer Science+Business Media New York.
RSC Advances (20462069)6(41)pp. 34940-34945
A new fluorescent and colorimetric chemosensor based on naphthothiazole S1 was synthesized and its applications as chemosensor for the selective sensing of pollutant metal ions in water resources and/or biological systems were investigated. Sensor S1 showed great selectivity for Zn2+ and Sn2+ over other metal ions. The Job's plot showed a 1 : 1 stoichiometry between S1 with Zn2+ and Sn2+. Interaction mode of sensor S1 with Zn2+ ion was further approved by single crystals X-ray crystallography method. The detection limit for the fluorescent chemosensor S1 toward Zn2+ and Sn2+ were respectively 2.60 × 10-8 M and 8.21 × 10-8 M. © The Royal Society of Chemistry 2016.
RSC Advances (20462069)6(85)pp. 81943-81949
A novel straightforward method for the synthesis of 2,3-disubstituted imidazo[1,2-a]pyridine derivatives in water as a truly safe and cheap reaction medium was developed. Hence, N-alkyl pyridinium and S-alkyl thiouronium salts were reacted in the presence of NaHCO3 as a mild base in water to produce imidazo[1,2-a]pyridines in moderate to excellent yields. © 2016 The Royal Society of Chemistry.
Journal Of The Iranian Chemical Society (1735207X)13(9)pp. 1571-1577
Abstract: A novel one-pot three-component reaction has been developed for construction of thiazole derivatives under solvent-free conditions. Hence, tertiary thioamides, α-haloketones, and NH4OAc were grinded together and allowed to react thermally at 110 °C and/or under microwave irradiation to produce the corresponding thiazole derivatives in very good yields. Graphical Abstract: [Figure not available: see fulltext.] © 2016, Iranian Chemical Society.
Synlett (09365214)26(13)pp. 1819-1822
A novel and simple procedure for the construction of fully substituted thiophene-2,4-diamines using tertiary thioamides was developed. Thus, thioacetomorpholides undergo self-condensation to the corresponding 3,5-diarylthiophene-2,4-diamine derivatives in the presence of iodine and potassium carbonate in a suitable solvent and under mild conditions. © Georg Thieme Verlag Stuttgart · New York.
Synlett (09365214)25(1)pp. 108-110
A new multicomponent domino reaction has been developed for the synthesis of 4-aminothiazole-2(3H)-thiones. Carbon disulfide was successfully used in the preparation of 4-aminothiazole-2(3H)-thione derivatives through reaction with primary amines and 2-bromo-2-arylacetonitriles in the presence of sodium carbonate and a catalytic amount of sodium iodide.
Molecular Diversity (1573501X)19(2)pp. 283-292
Several benzazoles (benzoxazoles, benzothiazoles, and benzimidazoles) and azoles (1H-1,2,4-triazole-5(4H)-thiones and 1,2,4-oxadiazoles) bearing a sulfonamide moiety were efficiently prepared via the reactions of dimethyl (arylsulfonyl) dithioimidocarbonate derivatives and their 2-aminobenzene precursors, thiosemicarbazides, and amidoximes, respectively, in the presence of K2CO3 as a base in aqueous ethanol (25 %) as a green media in moderate to excellent yields. © 2015, Springer International Publishing Switzerland.
Synthetic Communications (00397911)45(14)pp. 1681-1687
(Chemical Equation Presented) 2,4,6-Tribromo-1,3,5-trihydroxybenzene (TBTHB) as a reagent was efficiently reacted with 6 molar equivalents of benzothioamides in dimethyl sulfoxide (DMSO), and the corresponding 3,5-diaryl-1,2,4-thiadiazoles were obtained in almost quantitative yields (91-98%) and in short times (15-20 min) with the formation of hexahydroxybenzene as a rather valuable by-product. 2015 Copyright © Taylor & Francis Group, LLC.
Analytica Chimica Acta (00032670)825pp. 34-41
Gold electrode surface is modified via covalent attachment of a synthesized thiol functionalized with 8-hydroxyquinoline, p-((8-hydroxyquinoline)azo) benzenethiol (SHQ), for the first time. The behavior of the nanostructured electrode surface (Au-SHQ) is characterized by electrochemical techniques including cyclic and differential pulse voltammetry (CV and DPV), and electrochemical impedance spectroscopy (EIS). The modified surface is stable in a wide range of potentials and pHs. A surface pKa of 6.0±0.1 is obtained for Au-SHQ electrode using surface acid/base titration curves constructed by CV and EIS measurements as a function of pH. These results helped to determine the charge state of the surface as a function of pH. The gold modified electrode surface showed good affinity for sensing the Al(III) ion at pH 5.5. The sensing process is based on (i) accumulation and complex formation between Al(III) from the solution phase and 8HQ function on the Au electrode surface (recognition step) and (ii) monitoring the impedance of the Au-SHQ-Al(III) complex against redox reaction rate of parabenzoquinone (PBQ) (signal transduction step). The PBQ is found to be a more suitable probe for this purpose, after testing several others. Thus, the sensor was tested for quantitative determination of Al(III) from the solution phase. At the optimized conditions, a linear response, from 1.0×10-11 to 1.2×10-5M Al(III) in semi-logarithmic scale, with a detection limit of 8.32×10-12M and mean relative standard deviation of 3.2% for n=3 at 1.0×10-7M Al(III) is obtained. Possible interferences from coexisting cations and anions are also studied. The results show that many ions do not interfere significantly with the sensor response for Al(III). Validity of the method and applicability of the sensor are successfully tested by determination of Al(III) in human blood serum samples. © 2014 Elsevier B.V.
Synlett (09365214)25(14)pp. 2044-2048
The first zinc chloride catalyzed ring opening of N-arylsulfonyl aziridines by thioamides is described. Various thioamides were reacted with N-arylsulfonyl aziridines in the presence of a catalytic amount of dry zinc chloride to provide the corresponding N-arylsulfonyl amidine derivatives with good to excellent yields. © Georg Thieme Verlag Stuttgart New York.
Synthesis (Germany) (1437210X)45(7)pp. 913-918
A novel and simple procedure was developed for the construction of fully substituted thiophenes. A series of α-haloacetophenone derivatives were converted into fully substituted thiophenes by treatment with sodium sulfide in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene and sodium iodide in aqueous ethanol under aerobic conditions. A mechanism for the reaction is proposed. © Georg Thieme Verlag Stuttgart - New York.
Tetrahedron (14645416)69(1)pp. 38-42
The synergistic enhancement of metal ion extraction by azacrown ethers in the presence of carboxylic acids has been attributed to a ligand assembly effect in which these two ligands form a complex, facilitated by proton transfer, prior to complexation of the metal ion. In order to investigate the first steps in this multi-component complexation procedure, six tris-(azacrown) ethers were synthesised in high yields and their ability to complex mono- and tri-carboxylic acids was investigated by 1H NMR in methanol-d4. All six compounds bound to benzoic acid with 1:3 host-guest stoichiometry and four of them bound tricarboxylic acids with 1:1 host-guest stoichiometry, providing good support for the proposed first step in the ligand assembly effect. © 2012 Elsevier Ltd. All rights reserved.
Helvetica Chimica Acta (0018019X)95(7)pp. 1164-1168
A new one-step synthesis of highly substituted thiophen-2(3H)-one derivatives was developed. 2-Aryl-1-(morpholin-4-yl)ethanethiones were reacted with 2-chloro-2-phenylacetyl chloride in DMF in the presence of a base to give the title compounds in moderate-to-good yields. Copyright © 2012 Verlag Helvetica Chimica Acta AG, Zürich, Switzerland.
Journal of Organic Chemistry (15206904)77(13)pp. 5808-5812
Fully substituted 4-aminopyrrolones are easily accessed via simple routes starting from imines, ketones, or α-bromophenyl acetonitriles. Imines were reacted with KCN/NH 4Cl in aqueous ethanol to produce α-arylamino benzyl cyanides. On the other hand, ketones were transformed to the desired α-amino nitriles using a modified Strecker reaction. Then, α-amino nitrile precursors were allowed to react with a suitable acyl halide to produce the corresponding amides. Further treatment of these amides with ethanolic KOH converted them to highly substituted 4-amino-1H-pyrrol-2(5H)- one derivatives in moderate to excellent yields. © 2012 American Chemical Society.
Journal of Sulfur Chemistry (17415993)33(6)pp. 639-645
An efficient and one-step method for the preparation of highly substituted thiophenes and thiophen-2-yl-acetic acid derivatives was developed. Hence, thioacetomorpholides were smoothly reacted with -bromo carbonyl compounds in [bmim]OH as an efficient dual catalyst-reaction medium to produce the title compounds in good yields. © 2012 Taylor & Francis.
Journal of Sulfur Chemistry (17415993)33(2)pp. 165-170
In this paper, a facile and highly efficient synthesis of 3,5-disubstituted 1,2,4-thiadiazoles by oxidative dimerization of thioamides using pentylpyridinium tribromide is reported. © 2012 Copyright Taylor and Francis Group, LLC.
Journal of Sulfur Chemistry (17415993)33(3)pp. 285-293
A one-pot conversion of alcohols to thioesters using a sulfonated porous carbon (SPC) as a solid acid catalyst is reported. It was found that, when a tertiary, benzylic, or allylic alcohol was reacted with thioamides in the presence of SPC, the corresponding thioesters were produced in good to excellent yields in a short time. © 2012 Taylor & Francis.
Helvetica Chimica Acta (0018019X)94(11)pp. 2039-2044
Unexpectedly, in the reaction of 2-bromo-2-phenylacetonitrile derivatives with 2 mol-equiv. of benzothioamide in DMSO, 3,5-diaryl-1,2,4-thiadiazoles were obtained in excellent yields (83-90%) and in short reaction times (5-10 min). It is found that, in DMF, a quite different reaction takes place and 2,5-diaryl-1,3-thiazol-4-amines are formed as the main products. Copyright © 2011 Verlag Helvetica Chimica Acta AG, Zürich, Switzerland.
Bulletin of the Korean Chemical Society (02532964)32(4)pp. 1201-1203
A one-pot conversion of tertiary thioamides to S-2-oxo thioesters is reported. Hence, tertiary thioamides were reacted with α-halo ketones or acids under solvent-free conditions to produce the corresponding oxo-thioesters in good to excellent yields.
Synthetic Communications (00397911)41(19)pp. 2932-2938
1,3-Dibromo-5,5-diphenylimidazolidine-2,4-dione (N,N'-dibromo phenytoin) was efficiently used for the rapid conversion of thiobenzamides to the corresponding 3,5-diaryl-1,2,4-thiadiazoles in water-wet paste conditions. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file. © Taylor & Francis Group, LLC.
Synthetic Communications (00397911)41(16)pp. 2421-2429
Diverse thioesters were efficiently prepared via the solvent-free reaction of thioamide derivatives with alkyl halides in the presence of catalytic amounts of 1,4-diazabicyclo[2.2.2]octane (DABCO) in small quantities of water and in good to excellent yields. © 2011 Taylor & Francis Group, LLC.
Synlett (09365214)(19)pp. 2861-2866
A one-step conversion of alcohols into thioesters under solvent-free conditions is reported. The alcohols were reacted with primary thioamides in the presence of p-toluenesulfonic acid under solvent-free conditions to produce the corresponding thioesters in good to excellent yields. © Georg Thieme Verlag Stuttgart - New York.
European Journal of Organic Chemistry (10990690)(29)pp. 4926-4929
Benzazoles (benzoxazoles, benzothiazoles, and benzimidazoles) were efficiently prepared by the aquatic reaction of the corresponding thioamidinium salts and 2-aminophenol, 2-aminothiophenol, and 1,2-diaminobenzene, respectively. The thioamidinium salt was successfully applied as an alternative to a carboxylic acid derivative to react smoothly with an amino precursor and in the presence of catalytic amounts of hexadecyltrimethylammonium bromide salt to produce benzazoles in good to excellent yields. © Wiley-VCH Verlag GmbH & Co. KGaA 2009.
Journal Of The Iranian Chemical Society (1735207X)6(3)pp. 547-551
A novel and simple method for rapid conversion of thioamides to the corresponding 1,2,4-thiadiazole derivatives was developed. It was shown that, thioamides undergo clean and efficient oxidation and cyclization in their conversion to 1,2,4-thiadiazoles using N-benzyl-DABCO-tribromide in wet solid-solid conditions.
Helvetica Chimica Acta (0018019X)92(7)pp. 1268-1272
Thieno[2,3-b]indole derivatives were efficiently prepared via the reaction of 1,3-dihydro-2H-indole-2-thiones with α-bromo-substituted ketones or aldehydes and in the presence of Et3N (Scheme 2 and Table). The reaction took place under very mild conditions and in short times with good to excellent yields. © 2009 Verlag Helvetica Chimica Acta AG.
Green Chemistry- England (14639262)11(12)pp. 1987-1991
Thioesters were efficiently prepared via the direct reaction of tertiary thioamides and alkyl halides in water, and in the presence of catalytic amounts of NaI, hexadecyltrimethylammonium bromide (HTAB), and 1,4-diazabicyclo[2.2.2]octane (DABCO). Hence, thioamides smoothly undergo an S-alkylation with alkyl halides in aqueous media following by hydrolysis to afford the corresponding thioesters in very good to excellent yields. © 2009 The Royal Society of Chemistry.
Synthetic Communications (00397911)38(11)pp. 1694-1702
A convenient and efficient procedure was developed for preparing α,α′-icyanostilbenes through the oxidative coupling reaction of benzyl cyanide derivatives using N-benzyl DABCO tribromide as the oxidative bromination reagent in the presence of K2CO3 as a base. Copyright © Taylor & Francis Group, LLC.
Letters In Organic Chemistry (15701786)3(2)pp. 123-127
Various diesters successfully undergo a double Fries rearrangement to afford the corresponding bis o-hydroxylaryl ketones, in the presence of AlCl3 under microwave irradiation. © 2006 Bentham Science Publishers Ltd.
Synthetic Communications (00397911)36(8)pp. 1093-1096
N-Benzyl-DABCO-ammonium tribromide was found to be an efficient and recyclable reagent for the deprotection of dithioacetals in dichloromethane/ methanol at room temperature. The reaction can be performed cleanly, in short time, and in high yield. Copyright © Taylor & Francis Group, LLC.
Matloubi moghaddam, F.,
Zali boeini, H.,
Bagheri, M.,
Rüedi, P.,
Linden, A. Journal of Sulfur Chemistry (17415993)26(3)pp. 245-250
A novel, efficient, and very mild one-pot synthesis of methyl 2-[(Z)-4-aryl-5-morpholino-3-oxo-2,3-dihydrothiophen-2-ylidene]acetate derivatives under kinetic control has been developed. The title compounds were prepared by the reaction of thioacetomorpholides with dimethyl acetylenedicarboxylate (DMAD) in the presence of K2CO3 in a non-polar solvent with excellent yields. © 2005 Taylor & Francis.
Synlett (09365214)(10)pp. 1612-1614
N-benzyl-DABCO tribromide, a stable, crystalline organic ammonium tribromide (OATB), have been used as an alternative electrophilic bromine source for the efficient oxidative cyclization of thiobenzanilides to the corresponding benzothiazoles under mild conditions. © Georg Thieme Verlag Stuttgart.
Journal of Sulfur Chemistry (17415993)26(4-5)pp. 331-335
A solvent-free, solid-supported, and microwave-assisted thio-Claisen rearrangement of S-propargylated thioamides having an activated α-methylene group has been developed. The methodology could be used successfully for the synthesis of tri-substituted thiophenes and sulfur containing triarylamines. The reaction takes place in short time and in good isolated yield. © 2005 Taylor & Francis.
Tetrahedron (14645416)60(29)pp. 6085-6089
An efficient one-step method for the synthesis of fully substituted thiophenes, from thiomorpholides and α-halo ketones, was developed. A mechanism has also been proposed for the course of reaction. © 2004 Elsevier Ltd. All rights reserved.
Synthetic Communications (00397911)34(11)pp. 2071-2075
An AlCl3-ZnCl2 mixture supported on silica gel is found to be a new efficient medium for the Beckmann rearrangement in solvent-free conditions under microwave irradiation. The yields are good to excellent.
Tetrahedron Letters (00404039)44(33)pp. 6253-6255
An efficient method for the preparation of 2,3,5-trisubstituted thiophenes in a one-pot synthesis from thiomorpholides via the thio-Claisen rearrangement was developed. © 2003 Elsevier Ltd. All rights reserved.
Tetrahedron (14645416)57(31)pp. 6829-6832
The one-pot synthesis of several secondary amines and secondary amino esters are reported. Treatment of aldehydes (aliphatic or aromatic) with (trimethylsilyl)alkylamines, in the presence of 5 M lithium perchlorate in diethyl ether gives intermediate imines. Reaction of these intermediate imines with different nucleophiles and functionalized organozinc reagents, BrZnCH2COOR, produce a variety of secondary amines and N-alkyl- or N-arylamino esters in good yields. © 2001 Elsevier Science Ltd. All rights reserved.
