Showing papers in "Phosphorus Sulfur and Silicon and The Related Elements in 2014"
TL;DR: In this paper, a facile and efficient protocol for one-pot three-component synthesis of structurally diverse (2-amino-3-cyano-4H-chromen-4-yl)phosphonic acid diethyl esters from the reaction of salicylaldehydes, was proposed.
Abstract: A facile and efficient protocol for one-pot three-component synthesis of structurally diverse (2-amino-3-cyano-4H-chromen-4-yl)phosphonic acid diethyl esters from the reaction of salicylaldehydes, ...
37 citations
TL;DR: A simple and highly selective oxidation of sulfides to sulfoxides and an oxidative coupling of thiols with polyvinylpolypyrrolidoniume tribromide has been developed as mentioned in this paper.
Abstract: A simple and highly selective oxidation of sulfides to sulfoxides and an oxidative coupling of thiols with polyvinylpolypyrrolidoniume tribromide has been developed. A series of sulfides and thiols was oxidized selectively at room temperature in good to excellent yields.
33 citations
TL;DR: In this article, a series of symmetric 1,3-bis thiourea derivatives bearing aryl side chains were successfully synthesized from the reactions of amines with 3-acetylbenzoyl isothiocyanate and 4acetyl benzoyls isothianate, respectively.
Abstract: A series of symmetrical 1,3-bis thiourea 1a–e and 1,4-bis thiourea derivatives 2a–e have been successfully synthesized from the reactions of amines with 3-acetylbenzoyl isothiocyanate and 4-acetylbenzoyl isothiocyanate, respectively. All the synthesized compounds were characterized by FT-IR spectroscopy and 1H and 13C NMR spectroscopy. The compounds were screened for their antibacterial activity by turbidimetric method using gram-negative bacteria (E. coli ATCC 8739) using turbidimetric method. The newly synthesized bis-thiourea derivatives bearing aryl side chains showed good antibacterial activity against E. coli. The effect of the molecular structure of the synthesized compounds on the antibacterial activity is discussed.
26 citations
TL;DR: In this article, a new synthesis of CpBIGNa and FeCl2 in the presence of CO has been developed starting from CpBiGNa/FeCl2 and the reaction of this product with P4 leads to the two new Pn ligand complexes [CpBIGFe(η5-P5)] 1b and [(CpBiGFe)2(μ,η4:4: 4-P4]-(4-nBuC6H4)5)] (4) containing the highly sterically demanding
Abstract: A new synthesis of [CpBIGFe(CO)2]2 3 (CpBIG = C5(4-nBuC6H4)5) was developed starting from CpBIGNa and FeCl2 in the presence of CO. Reaction of this product with P4 leads to the two new Pn ligand complexes [CpBIGFe(η5-P5)] 1b and [(CpBIGFe)2(μ,η4:4-P4)] (4) containing the highly sterically demanding CpBIG ligand. Depending on the solvent, different ratios of 1b:4 are obtained. The products 1b, 3, and 4 were characterized by spectroscopic methods as well as by X-ray diffraction.
24 citations
TL;DR: Titania sulfonic acid (TiO2-SO3H) is easily prepared by the reaction of TiO2 with neat chlorosulfonic acid and characterized using a variety of techniques, including infrared, x-ray diffraction, and Br...
Abstract: Titania sulfonic acid (TiO2-SO3H) is easily prepared by the reaction of TiO2 with neat chlorosulfonic acid and characterized using a variety of techniques, including infrared, x-ray diffraction, Br...
22 citations
TL;DR: In this paper, two phosphorus-nitrogen-containing flame retardants, 1,1′,2,2′-tetra-hydroxyl-4′, 4′-biphenylene-bis[amino]-((10′′′-O-10′-′-H-9′′,′-oxa-10-6-phosphaphenanthrene-10.5-methyl)-bisphenol, imine (1), was synthesized through condensation reaction between 3,4-dihydroxyben
Abstract: GRAPHICAL ABSTRACT Abstract Two novel phosphorus-nitrogen-containing flame retardants, 1,1′,2,2′-tetra-hydroxyl-4′′, 4′′′-biphenylene-bis[amino-((10′′′′-O-10′′′′-H-9′′′′-oxa-10′′′′λ5-phosphaphenanthrene-10′′′′-yl))-methyl]}-bisphenol (3) and 1,1′,2,2′-tetra-hydroxyl-{4′′,4′′′-phenylene-bis[amino-((10′′′′- O-10′′′′- H-9′′′′- oxa-10′′′′λ5-phosphaphenanthrene-10′′′′-yl))-methyl]}-bis-phenol (4) were synthesized by two steps: 1,1′,2,2′-tetra-hydroxyl-{4′′,4′′′- bi-phenylene-bis[amino-methyl]}-bis-phenol, imine (1), was synthesized through condensation reaction between 3,4-dihydroxybenzaldehyde and 4,4′-diaminobiphenyl; and, 1,1′,2,2′-tetra-hydroxyl-{4′′,4′′′- phenylene-bis[amino-methyl]}-bis-phenol, imine (2) was synthesized by the reaction of 3,4-dihydroxybenzaldehyde and 1,4-phenylenediamine; then, addition reactions between 9,10-dihydro-9-oxa-10- phosphaphenanthrene-10-oxide and the two imines, the (3) and (4) were obtained, respectively. (1)–(4) were characterized by FTIR, NMR, and MS. (3) and (4) reacted with epoxy resins as co-curing agents with 4,4′-diaminodiphenylmethane. Compared with control samples, (3) or (4) co-cured epoxy thermosets with phosphorus content of 1.0 wt% possessed good flame retardant properties with LOI value reaching more than 36.0, higher char yields. The glass translation temperature (Tg) of thermosets containing (3) or (4) were characterized with suitable changes by DSC test.
22 citations
TL;DR: In this article, four intumescent flame retardants containing phosphaphenanthrene and phosphazene groups were synthesized by using the classic Atherton-Todd reaction and Kabachnik-Fields reactions.
Abstract: Four novel intumescent flame retardants containing phosphaphenanthrene and phosphazene groups were synthesized by using the classic Atherton–Todd reaction and Kabachnik–Fields reactions. 9, 10-dihy...
21 citations
TL;DR: In this paper, 4-(N,N-Dimethylamino)pyridine (DMAP), with a dual role as a basic nucleophilic catalyst, was shown to be a highly efficient catalyst for the synthesis of some new N-(2-aryl-7-benzyl-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidin-4-amines (7-deazaadenines) with benzenesulfonyl chlorides.
Abstract: 4-(N,N-Dimethylamino)pyridine (DMAP), with a dual role as a basic nucleophilic catalyst, was shown to be a highly efficient catalyst for the synthesis of some new N-(2-aryl-7-benzyl-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)benzenesulfonamides through the reaction of 2-aryl-7-benzyl-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidin-4-amines (7-deazaadenines) with benzenesulfonyl chlorides. It was also found that the use of DMAP under solvent-free conditions is much more effective than other catalytic systems such as pyridine as both the catalyst and solvent, t-BuOK in t-BuOH, Et3N in ethanol (EtOH), and even DMAP in dimethylformamide (DMF). The influences of the reaction parameters, temperature, and the catalyst amount, on the catalytic performance have been studied. All synthetic compounds were characterized on the basis of their full spectral data.
21 citations
TL;DR: In this paper, a new 1,2,3-thiadiazole compound, C15H14FN5 O2S2, has been synthesized and the crystal structure was determined by single crystal X-ray diffraction study.
Abstract: A new 1,2,3-thiadiazole compound containing 1,2,4-triazole moiety, C15H14FN5 O2S2, has been synthesized and the crystal structure was determined by single crystal X-ray diffraction study. The biological activity of the title compound was determined and the results showed that title compounds 10 showed higher inhibition abilities of rape root than the control cyclopropane-1,1-dicarboxylic acid at 100 μg/mL (73%) and weak activity against Echinochloa crusgalli (28%) and KARI (35%) at 100 μg/mL. [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental files: additional text, figures, tables.]
20 citations
TL;DR: In this article, a convenient route for the synthesis of optically active methyl, phenyl, and dimonoterpenyl sulfides derived from carane, p-menthane, pinane, and bornane was developed.
Abstract: Convenient routes for the synthesis of optically active methyl, phenyl, and dimonoterpenyl sulfides derived from carane, p-menthane, pinane, and bornane were developed. Methyl and dimonoterpenyl sulfides have been obtained by the reaction of the corresponding monoterpene thiolates with methyl iodide or monoterpene tosylates. The reactions of monoterpene tosylates with sodium benzenethiolate gave the corresponding phenyl monoterpenyl sulfides. These sulfides were used for the sulfur ylide-mediated reaction to yield epoxides. Good diastereoselectivities up to 99:1 and low to moderate enantioselectivities were observed for the enantioselective synthesis of chiral epoxides.
19 citations
TL;DR: Organic dithiocarbamates have received great attention due to their interesting chemistry and wide utility as radical precursors and intermediates in organic synthesis, and they also have found many of applications, that is, in agriculture and medicine as mentioned in this paper.
Abstract: Organic dithiocarbamates have received great attention due to their interesting chemistry and wide utility as radical precursors and intermediates in organic synthesis. They also have found many of applications, that is, in agriculture and medicine. They are in use as pesticides, as well as in the rubber industries as vulcanization accelerators; and as antioxidants. Because they exhibit strong metal-binding capacity, they can act as in inhibitors of enzymes and have a profound effect on biological systems. Moreover, they have found application in the treatment of cancer and HIV.
TL;DR: A review of the anticancer activity of representative α-aminophosphonic acid derivatives is presented in this article, with comments where possible on modes of action and preliminary in vitro screening results are also presented for selected dialkyl α-aryl (or hetero-aryl)-α-(diphenylmethylamino)methanephosphonates against the National Cancer Institute (NCI) 60-cell line panel of human tumor cells, which showed average response parameters for active compounds of GI50 between 4.81 × 10−6 and 2.40
Abstract: Reports on the anticancer activity of representative α-aminophosphonic acid derivatives are briefly reviewed, with comments where possible on modes of action. Preliminary in vitro screening results are also presented for selected dialkyl α-aryl (or heteroaryl)-α-(diphenylmethylamino)methanephosphonates against the National Cancer Institute (NCI) 60-cell line panel of human tumor cells, which showed average response parameters for active compounds of GI50 between 4.81 × 10−6 and 2.40 × 10−5 M, TGI between 1.88 and 6.28 × 10−5 M, and LC50 between 5.71 and 9.37 × 10−5 M. The highest activity was shown by the α-phenyl compound for which GI50 10−7 M was recorded against leukemia cell line MOLT-4.
TL;DR: A series of novel sulfonylureas and N-acylsulfonamides derivatives were synthesized and characterized by 1H NMR, 13C NMR and HRMS.
Abstract: A series of novel sulfonylureas and N-acylsulfonamides derivatives were synthesized and characterized by 1H NMR, 13C NMR, and HRMS. These compounds were synthesized efficiently in two steps (carbam...
TL;DR: In this paper, six organotin(IV) complexes of type Me2SnL2, Bu2snL2 and Ph3SnL have been synthesized by the reactions of the corresponding diorganotin (IV) oxide and triphenyltin(IV)-hydroxide with respective indole-3-butyric acid (IBH) or indole 3-propionic acid (IPH) in the desired molar ratios of 1:2/1:1.
Abstract: Six organotin(IV) complexes of type Me2SnL2, Bu2SnL2, and Ph3SnL [where L = indole-3-butyric acid (1, 2 and 3) or indole-3-propionic acid (4, 5 and 6)] have been synthesized by the reactions of the corresponding diorganotin(IV) oxide and triphenyltin(IV) hydroxide with respective indole-3-butyric acid (IBH) or indole-3-propionic acid (IPH) in the desired molar ratios of 1:2/1:1. All of the compounds have been characterized by elemental analysis, IR, 1H NMR, 13C NMR, and 119Sn NMR spectroscopy. Thermal studies of all synthesized complexes have been carried out using thermogravimetry (TG) technique under a nitrogen atmosphere. The thermal decompositions for compounds Me2SnL2 and Bu2SnL2 occurred in two steps, whereas in compounds Ph3SnL, it exhibited as three steps decomposition and resulted into the formation of pure SnO2. The complexes were also screened against three gram-positive (Staphylococcus aureus, Staphylococcus epidermidis, and Micrococcus luteus) and three gram-negative (Escherichia col...
TL;DR: In this paper, a series of 2-amino-5-selenothiazoles were synthesized as an anti-inflammatory and analgesic agent and evaluated as anti-inflammation agent.
Abstract: GRAPHICAL ABSTRACT Abstract Treatment of 2-aminothiazole (1) with triselenium dicyanide (2) afforded selenocyanate (3). Reduction of 3 with NaBH4 gave the diselenide 4. Compounds 3 and 4 were used as a key intermediate for the synthesis of a series of 2-amino-5-selenothiazoles. The newly synthesized compounds were evaluated as anti-inflammatory and analgesic agent.
TL;DR: In this paper, the use of (−)-(S)- and (+)-(R) enantiomers of t-butylphenylphosphinothioic acid as a chiral solvating agent for the determination of enantiomeric purity is discussed.
Abstract: Synthesis, structural studies and the use of the (−)-(S)- and (+)-(R) enantiomers of t-butylphenylphosphinothioic acid as a chiral solvating agent for the determination of enantiomeric purity is discussed. Systems that are the most extensively studied are emphasized.
TL;DR: A series of pyrazole derivatives containing substituted phenylsulfinyl/sulfonyl group have been synthesized via the oxidation of intermediate pyrazoles sulfoether with H2O2 in acetic acid.
Abstract: A novel series of pyrazole derivatives containing substituted phenylsulfinyl/sulfonyl group have been synthesized via the oxidation of intermediate pyrazole sulfoether with H2O2 in acetic acid. The novel compounds were characterized by melting point, 1H NMR, FT-IR, MS, and elemental analysis or HRMS. The biological activity results showed that most of the title compounds exhibit significant fungicidal activities against Alternaria solani Sorauer, Phytophthora capsici, and Corynespora cassiicola. [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental files: Additional text and figures.]
TL;DR: The antioxidant properties of pyridylselenium compounds have been evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical and nitric oxide (NO) scavenging methods.
Abstract: The antioxidant activity of pyridylselenium compounds has been evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical and nitric oxide (NO) scavenging methods. Pyridylselenium compounds have shown far superior (100–1000 times) antioxidant property than ebselen. The control release of bis(2-pyridyl) diselenide from poly(acrylamide) hydrogels has been studied in order to evaluate its release mechanism and diffusion coefficient. The later study also demonstrates that the pyridylselenium loading into the polymer matrix increases the magnitude and the rate of the radical scavenging activity of the poly(acrylamide) hydrogels.
TL;DR: In this article, a novel cyclotriphosphazene-based epoxy monomer, hexa-[4-(glycidyloxycarbonyl) phenoxy]cyclotriaphosphazenes (HGCP), was synthesized via a four-step synthetic route, and fully characterized by 1H, 13C, and 31P NMR spectroscopy, high-resolution mass spectrometry, and elemental analysis.
Abstract: A novel cyclotriphosphazene-based epoxy monomer, hexa-[4-(glycidyloxycarbonyl) phenoxy]cyclotriphosphazene (HGCP), was synthesized via a four-step synthetic route, and fully characterized by 1H, 13C, and 31P NMR spectroscopy, high-resolution mass spectrometry, and elemental analysis. Thermosetting systems based on HGCP with three curing agents, for example, 4,4′-diaminodiphenylsulfone (DDS), 4,4′-diaminodiphenylmethane (DDM), and dicyandiamide (DICY), were used for making a comparison of their thermal curing behaviors. The curing behaviors were measured by differential scanning calorimetry. Moreover, flame retardancy of HGCP thermosetting systems was estimated by Limiting Oxygen Index (LOI) and Vertical Burning Test (UL-94). The resulting HGCP thermosetting systems exhibited better flame retardancy than the common epoxy resins diglycidyl ether of bisphenol A (DGEBA) and the regular brominated bisphenol A epoxy resin (TBBA) cured by DDS, respectively. When HGCP was cured by DDS, its thermosetting ...
TL;DR: In this article, a new polymer-supported camphor-derived sulfide catalyst was proposed, which exhibited higher enantioselectivity in asymmetric epoxidation of benzaldehydes and benzyl bromide.
Abstract: A new polymer-supported camphor-derived sulfide catalyst was prepared. Compared with the homologous catalyst, the immobilized catalyst exhibited higher enantioselectivity in asymmetric epoxidation of benzaldehydes and benzyl bromide. The catalyst can be recycled at least 5 times with only minimal loss of catalytic performance.
TL;DR: An efficient and simple method for the preparation of 1-methyl-3-(2-(sulfooxy)ethyl)-1H-imidazol-3-ium thiocyanate (SCN) as a Bronsted acidic ionic liquid (BAIL) is described in this paper.
Abstract: An efficient and simple method for the preparation of 1-methyl-3-(2-(sulfooxy)ethyl)-1H-imidazol-3-ium thiocyanate ([Msei]SCN) as a Bronsted acidic ionic liquid (BAIL) is described, and it is used in the highly efficient regioselective thiocyanation of aromatic and heteroaromatic compounds via a green and simple protocol [Msei]SCN as a novel IL and thiocyanation agent, H2O2 as a mild and environmentally friendly oxidant, and H2O:ethanol(1:4) as a solvent were used This procedure provided the target thiocyanates in high yield and very short reaction time [Supplementary materials are available for this article Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental files: Additional figures]
TL;DR: In this article, 2-thioxo and 2-oxo were synthesized in very high yields in 40min through a direct condensation of an equimolar amount of an aldehyde, malononitrile, and thiourea/urea under ball mill solvent-free and catalyst-free conditions.
Abstract: Various 2-thioxo and 2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carbonitriles were synthesized in very high yields in 40 min through a direct condensation of an equimolar amount of an aldehyde, malononitrile, and thiourea/urea under ball mill solvent-free and catalyst-free conditions.
TL;DR: In this article, the synthesis and spectral analysis of new Schiff base hydrazone derivatives were presented by the reaction of [(4-phenyl-5-substituted-4H1,2,4-triazol-3-yl)sulfanyl] acetohydrazide with various aldehydes.
Abstract: This study presents the synthesis and spectral analysis of new Schiff base hydrazone derivatives. New compounds were prepared by the reaction of [(4-phenyl-5-substituted-4H1,2,4-triazol-3-yl)sulfanyl] acetohydrazide with various aldehydes. The structures of the prepared compounds were confirmed by means of 1H NMR, 13C NMR, and elemental analyses. All synthesized compounds were screened for their in vitro antimicrobial activity by using the agar dilution technique against four reference strains of Gram-positive and Gram-negative bacteria and 12 yeasts belonging to Candida spp.
TL;DR: In this paper, two silyl-substituted silolide dianions (11a, 11b) have been synthesized and characterized spectroscopically.
Abstract: Two new silyl-substituted silolide dianions (11a, 11b) have been synthesized and characterized spectroscopically. Their 1H, 29Si, and 13C NMR spectra show similarities to the known phenyl- and alkyl-substituted analogues. Reaction with ethyl bromide gave the expected diethylsilol. B3LYP/6-31 + G* geometry optimization revealed equalized CC distances, and also NICS values indicate significant aromaticity.Figures S1—S5 are available online in Supplemental Materials.
TL;DR: A series of four different armed heterocyclic candidates, 1-(2-methyl-2,3dihydro-1,3-benzothiazol-2-yl)acetone (2), 1-(3-methyl)-4H-1-4-benzinothiazin-2 -yl)ethanone (3), 2-[(2-aminophenyl)dithio]aniline (4), and 3-hydroxy-3methyl-4-(3]-2-quinoxalinyl)-2-butan
Abstract: A series of four different armed heterocyclic candidates; 1-(2-methyl-2,3-dihydro-1,3-benzothiazol-2-yl)acetone (2), 1-(3-methyl-4H-1,4-benzothiazin-2-yl)ethanone (3), 2-[(2-aminophenyl)dithio]aniline (4), and 3-hydroxy-3-methyl-4-(3-methyl-2-quinoxalinyl)-2-butanone (5) have been prepared and their microbial activities were evaluated. A correlation of the structure and activities relationships of these compounds with respect to molecular modeling, Lipinski Rule of Five, drug likeness, toxicity profiles, and other physico-chemical properties of drugs are described and verified experimentally.
TL;DR: In this paper, a tripodal O-donor ligand, tris(2-N,N-dibutylcarbamoylmethoxyphenyl)phosphine oxide (L), was synthesized.
Abstract: A new tripodal O-donor ligand, tris(2-N,N-dibutylcarbamoylmethoxyphenyl)phosphine oxide (L), was synthesized. This potentially tetradentate ligand L exhibits variable denticity upon complexation with UO2(NO3)2, Nd(NO3)3, and Lu(NO3)3. The complexes were studied by elemental analysis, IR, and 1H, 13C, and 31P NMR spectroscopy.[Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental files: Additional text, tables, and figures.]
TL;DR: In this article, a new class of diethyl(3,5-dibromo-4-hydroxyphenylamino) (substituted phenyl/heterocyclic) methylphosphonates 4(a-j) has been synthesized by one-pot three component simultaneous reaction (Kabachnik-Fields) of 4-amino-2,6-Dibromophenol 1, substituted heterocyCLic/phenyl aldehydes 2(a−j), and dietHylph
Abstract: A new class of diethyl(3,5-dibromo-4-hydroxyphenylamino) (substituted phenyl/heterocyclic) methylphosphonates 4(a–j) has been synthesized by one-pot three component simultaneous reaction (Kabachnik–Fields) of 4-amino-2,6-dibromophenol 1, substituted heterocyclic/phenyl aldehydes 2(a–j), and diethylphosphite 3 using a Lewis acid catalyst, CeCl3·7H2O (5 mol%) under microwave irradiation as well as conventional conditions. It was observed that microwave irradiation method is more facile, efficient, and advantageous with respect to reaction time and yields. The structures of all the synthesized compounds were supported by analyzing IR, 1H/13C/31P NMR, and mass spectral data. The synthesized compounds were screened for their in vitro antimicrobial and antioxidant activities.
TL;DR: In this article, the reaction of tris(trimethylsilyl)phosphine and a mixture of two different N,N-dimethylalkylamides (1a,b), followed by the treatment with dry hydrazine in situ, resulted in seven asymmetrical 3,5...
Abstract: The reaction of tris(trimethylsilyl)phosphine and a mixture of two different N,N-dimethylalkylamides (1a,b), followed by the treatment with dry hydrazine in situ, resulted in seven asymmetrical 3,5...
TL;DR: In this article, the Biginelli reaction using aldehyde, thiourea, and 1,3-dicarbonyl compounds was performed smoothly in ethyl lactate (EL) with the catalysis of trimethylsilyl chloride (TMSCl).
Abstract: The three-component Biginelli reaction using aldehyde, thiourea, and 1,3-dicarbonyl compounds was performed smoothly in ethyl lactate (EL) with the catalysis of trimethylsilyl chloride (TMSCl). A class of 3,4-dihydropyrimidinthiones (DHPMs) were synthesized in good to excellent yields via the bio-based solvent mediated catalytic protocol.
TL;DR: In this article, some novel 1,3,4-oxadiazole derivatives containing 1,2,3-thiadiazoles were synthesized under microwave-assistant condition by multi-step reactions.
Abstract: Some novel 1,3,4-oxadiazole derivatives containing 1,2,3-thiadiazole were synthesized under microwave-assistant condition by multi-step reactions The structures were characterized by 1H NMR, MS, a