Tandem conjugate addition–alkylation reaction of various amines with α-bromo-α, β-unsaturated ketones resulted in near-quantitative conversions into the corresponding aziridines when the reaction was carried out in the presence of 10 mol% of phase-transfer, PT catalysts in water. Some chiral quaternary ammonium salts derived from Cinchona alkaloids were investigated as water-stable PT catalysts. The

This study was performed to understand the site selectivity in the reaction between β-himachalene and meta-chloroperbenzoic acid (m-CPBA) in the first step followed by the addition of dibromocarbene (CBr2) to the main monoepoxidation product Pα formed in the first reaction. Calculations were performed using the Becke three-parameter hybrid exchange functional and the Lee–Yang–Parr correlation functional

Some new fluorinated/nonfluorinated α-amino acids bearing 3-thioxo-5-oxo-1,2,4-triazin-6-yl and steroidal moieties have been obtained from condensation of the corresponding amino-triazinones with the steroid (Epiandrosterone). This was followed by the addition of HCN and, finally, acidic hydrolysis. The structure of the targets was established from their elemental analysis and spectral data. The amylolytic

The reaction of 4-benzoyl-5-phenylamino-2,3-dihydrothiophene-2,3-dione (1) with aminoheteroaryls, lamotrigine, 1,3-diaminoheteroaryls, dapsone, NH2R (hydroxylamine, DL-1-phenylethylamine, and metformin), and 4,4′-bipyridine in THF/H2O (1 : 1) at room temperature led to 3-N-phenylthiocarbamoyl-2-butenamides 2–5, while that with naphthylamines and 1,3-phenylenediamine in ethanol at high temperature led

The synthesis of 1H-indazolo[1,2-b]phthalazine-1,6,11(13H)-trione derivatives, using one-pot three-component condensation reaction of 3-nitrophthalic anhydride, hydrazine monohydrate, dimedone, and aromatic aldehydes in the presence of ZrO(NO3)2.2H2O as the novel catalyst and in reflux conditions in EtOH was reported. Quantum theoretical calculations for three structures of compounds (5a, 5b, and 5c)

Dichlorophosphoranides featuring N,N-dimethyl-N′-arylformamidine substituents were isolated as individual compounds. Dichlorophosphoranide 9 was prepared by the multicomponent reaction of C-trimethylsilyl-N,N-dimethyl-N′-phenylformamidine and N,N-dimethyl-N′-phenylformamidine with phosphorus trichloride. Its molecular structure derived from a single-crystal X-ray diffraction was compared to the analogous

A versatile method for the synthesis of new oxindoles was developed by the reaction between substituted isatins and 5-aminopyrazoles. The reaction was carried out at room temperature in ethanol using p-toluenesulfonic acid as the catalyst. The products were obtained with acceptable to excellent yields (44–96%). Structures of the new compounds were unambiguously established by spectroscopic and analytical

Condensation of 2,3-dichloropyrazine with 2-aminobenzenetellurole and 2-amino-5-methylbenzenetellurole, generated in situ by reduction of the corresponding ditellurides, resulted in the formation of novel 10H-pyrazino[2,3-b][1,4]benzotellurazine and its 7-methyl derivative. The products were purified via their well-crystallized 5,5-dibromo derivatives. X-ray crystallographic analysis of the title compound

New epoxides, derivatives of pyridine, 2,2′-bipyridine, and 1,10-phenanthroline, were synthesized from the respective α-methylazaarenes. The obtained racemic 2-oxiranyl-azaarenes along with styrene oxide and trans-stilbene oxide were submitted to the ring opening with chiral primary amines as a chiral auxiliary. The most effective reaction was run in the presence of Sc(OTf)3/diisopropylethylamine for

1,2,4-Triazine and 1,2,5-oxadiazine derivatives 2–12 were obtained from treated 1,3-oxazolone (1) with phenyl hydrazine or hydroxylamine hydrochloride. Chlorotriazine derivative 3 undergoing condensation reactions with different reagents produced new fused tetrazolo-triazine and triazino-quinazolinone derivatives. 1,2,5-Oxadiazine has been used as a synthon for the fused pyrazolo-oxadiazine derivative

This work reports an efficient method for the oxidation reaction of aliphatic, aromatic allylic, and benzylic alcohols into aldehydes catalyzed by the cyclopentadienyl ruthenium(II) complex (RuCpCl(PPh3)2) with bubbled O2. Through further optimizing controlled studies, the tendency order of oxidation reactivity was determined as follows: benzylic alcohols > aromatic allylic alcohols >> aliphatic alcohols

Structure and bonding of hybrid group 13/14 pyramidal molecules ClE[ R4] (E = B–Ga, E′ = C–Ge, R = SiMe3, SiMetBu2) were studied by DFT calculations. Six pyramidal structures are suggested for their potential synthetic realization.

A new domino reaction between thioaurones and malononitrile has been reported. This reaction allows efficient access to benzothiophene-fused pyran derivatives in good yields under mild reaction conditions. The substrate scope is broad; a series of benzothiophene-fused pyran derivatives have been synthesized.

The host-guest complexation of six amine boranes (R3NBH3) by the macrocyclic host molecule cucurbit uril (CB ) in aqueous solution has been investigated using 1H and 11B NMR spectroscopy. The limiting complexation-induced 1H and 11B chemical shift changes indicate that the amine boranes are included in the hydrophobic cavity of the host molecule. The host-guest stability constants for neutral R3NBH3∙CB

Phosphole P(V) derivatives are interesting building blocks for various applications from ligand synthesis to material sciences. We herein describe the preparation and characterisation of new 2,4-disubstituted oxo-, thiooxo-, and selenooxophospholes. The nature of the substituents on the phosphole ring determines the reactivity of these compounds towards homodimerization reactions. Aryl and trimethylsilyl

To understand the stability, chelation behaviour, and biological activity of 4-Formylpyridinethiosemicarbazone (H4FPT), it is important to recognize its interactive geometry. Hence, computational studies on geometrically optimized structures of thione and thiol forms of H4FPT were performed. Binary metal complexes of the ligand, H4FPT (L) with the Ni(II) and Cu(II) metal ions (M), were synthesized

Methylthioanilines, a series of sulfur-nitrogen donor ligands substituted with OCH3, CH3, Cl, and Br, and their copper(II) complexes have been synthesized and characterized by 1H and 13C NMR, elemental analysis, FTIR, UV-Vis and EPR spectra, molar conductance, and magnetic susceptibility measurements. The NMR spectra of the ligands revealed that the para/ortho protons and para carbon were sensitive

Diaryl(iodo)bismuthanes possessing a hypervalent C=O•••Bi–I bond were conveniently synthesized in a one-pot reaction by using arylzinc reagents generated from o-carbonyl iodobenzenes and zinc powder under ultrasonication. This method is superior to the conventional organolithium and Grignard methods because it has a wide functional group tolerance, requires no protecting group manipulations, and proceeds

N-tert-Butyl-1,2-diaminoethane was shown to react rapidly with atmospheric carbon dioxide to generate the zwitterionic ammonium carbamate salt CO2N(H)C2H4N Bu (1). Reaction of N-tert-butyl-1,2-diaminoethane with triethylorthoformate gave 1-tert-butyl-2-imidazoline (2) in 24% yield after fractional distillation, and the hydroxyalkyl-tethered imidazolinium salt [HOC(Me)2CH2NC2H4N(CH)tBu][Cl] (3) was

In this study we are going to present thiazole based carbohydrazide in search of potent antidiabetic agent as α-amylase inhibitors. Thiazole based carbohydrazide derivatives 1-25 have been synthesized, characterized by 1HNMR, 13CNMR, and EI-MS, and evaluated for α-amylase inhibition. Except compound 11 all analogs showed α-amylase inhibitory activity with IC50 values from 1.709 ± 0.12 to 3.049 ± 0

Detailed NMR spectral analysis of DMSO-d6 solutions of the series of substituted 2-phenacylbenzimidazoles (ketimine form, K) reveals two from three tautomeric forms. Integrals of the 1H NMR signals are used in establishing the molar ratio of tautomers. The experimental analyses are supported by quantum-chemical calculations, which satisfactorily reproduced the experimental trends. Although the reported

The X-ray crystal structures of three N-heterocyclic germylenes (NHGes) have been elucidated including the previously unknown 1,3-bis(2,6-dimethylphenyl)diazagermol-2-ylidene (1). In addition, the X-ray crystal structures of the previously synthesised 1,3-bis(2,4,6-trimethylphenyl)diazagermol-2-ylidene (2) and 1,3-bis(2,6-diisopropylphenyl)diazagermol-2-ylidene (3) are also reported. The discrete molecular

This contribution sets out to compute thermochemical and geometrical parameters of the complete series of chlorinated isomers of thiophene based on the accurate chemistry model of CBS-QB3. Herein, we compute standard entropies, standard enthalpies of formation, standard Gibbs free energies of formation, and heat capacities. Our calculated enthalpy values agree with available limited experimental values

We describe, herein, the synthesis, full characterization, and optical properties of four different ligands L1-L4 which associate an azo group, an imidazole unit, and a Schiff base fragment. The UV-visible absorption bands are characteristic of and transitions with an additional charge transfer between the azobenzene moiety and the imino group. Finally the determination of MIC80 values against pathogenic

A series of new 1,4-naphtho- and benzoquinone derivatives possessing N-, S-, O-substituted groups which has not been reported yet has been synthesized from 2,3-dichloro-1,4-naphthoquinone 1 and 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione 15 involving a Michael addition. In the synthesized compounds, antimicrobial activity at low concentrations against Escherichia coli B-906, Staphylococcus aureus

A facile Selectfluor-mediated oxidative method for direct introduction of SCN and SeCN groups into diversely substituted indoles and carbazoles is described, by employing readily available thiocyanate and selenocyanate salts, and the scope of the method is underscored by providing 24 examples. The feasibility to sequentially introduce SCN followed by SeCN on a carbazole framework and to synthesize

Iron complex-catalyzed dehydrogenative Sn‒E (E = S, Se) bond formation of hydrostannane with thiol and selenol was achieved. All new compounds were fully characterized using H, C{H}, Se{H}, and Sn{H} NMR measurements and elemental analyses. The structure of 1,1'-(1,3-dithia-2,2-dibutylstanyl)-[3]ferrocenophane was confirmed by single crystal

A tribute to Professor Naomichi Furukawa on the Occasion of his 82nd birthday By Invitation only Contract grant sponsor: JSPS KAKENHI Contract grant number: 18H01961 Contract grant number: 15K05392 Contract grant number: 18K05036 1Department of Fundamental Sciences, Graduate School of Science and Technology, Niigata University, Niigata, Japan 2Center for Coordination of Research Facilities, Institute

The utilization of carbon dioxide for the synthesis of valuable chemicals via an environmentally benign method has attracted great attention from organic chemists. The high atomeconomical cycloaddition of CO2 with epoxides for the preparation of cyclic carbonates is one of the most important protocols which is broadly presented in the literature. Assynthesized cyclic carbonates are used as processing

Spanish Ministerio de Economia, Industria y Competitividad, Grant/Award Number: CTQ2015-63997-C2-2-P; Comunidad Autonoma de Madrid, Grant/Award Number: FOTOCARBON, ref S2013/MIT284

The resolution of 1-isopentyl-3-methyl-3-phospholene 1-oxide via the formation of diastereomeric complexes using TADDOL derivatives or the Ca2+-salts of tartaric acid derivatives was studied. Both enantiomers of the 1-isopentyl-3-phospholene oxide were prepared in an enantiopure form with (R,R)-spiro-TADDOL, or with the acidic Ca2+-salt of O,O′-dibenzoyl-(R,R)-tartaric acid. The absolute configuration

Eight new aminoboron compounds derived from primary diamines and the pinacol-protected product of 3-fluoro-2-formylphenylboronic acid have been prepared and characterized fully. Reactions proceed to give the corresponding cyclic products arising via initial aldimine formation followed by a secondary hydroamination step. One compound contains a pendant amine group which was used to make a novel boron-containing

The convenient syntheses of new organophosphorus-substituted benzofulvenes with indenyl moieties from bis(trimethylsilyl) inden-2-ylphosphonate and substituted azomethines in the presence of the effective initiator-sodium hydride are developed. The following treatment of phosphonates with methanolic sodium methylate gives stable water-soluble disodium salts of corresponding phosphonic acids.

The synthesis of N-acylated 5-sulfonyl 8-aminoquinolines has been performed via the three-component reactions of 8-aminoquinolines, acyl chlorides and sodium sulfinates for the first time. This new synthetic approach is highly facile by employing cheap copper salt as promoter and enabling the product formation via domino N-acylation and selective remote C-5 sulfonylation.

Reaction of 6,7-bis(chloromethyl)-1,2,3,4-tetrahydronaphthalene with tellurium powder and potassium iodide in 2-butoxyethanol gave 2,2-diiodo-1,3,5,6,7,8-hexahydro-naphtho[2,3-c]tellurophene(1) as a red-orange solid in 40% yield. Reduction of 1 with hydrazine hydrate gave a pale yellow solid of 1,3,5,6,7,8-hexahydronaphtho[2,3-c]telluro-phene(2) in 80% yield. Chlorination, bromination of 2 and its

This research reports a novel method for synthesizing new thiazole thioglycosides. This series of thiazole thioglycosides were designed by the reaction of potassium cyanocarbonimidodithioate 2 with benzoyl acetonitrile 3a and ethyl bromoacetate 3b in the presence of ethanol-KOH to give the corresponding potassium 4-amino-5-substituted-thiazole-2-thiolates 4a,b. The latter compounds were treated with

An efficient protocol for C-O and C-S bonds formation by the cross-coupling reaction of 1,2-di(pyrimidin-2-yl) disulfides with phenols/thiophenols promoted by copper(I) chloride was established. It was discovered that variously substituted di(hetero)aryl disulfides and phenols were well tolerated. This strategy is the conversion of disulfides into hetero-aryl ethers and thioethers by a copper-promoted

Reactions of 9-substituted guanine derivatives with NaH/1,2-dibromoethane, 1,3-dibromopropane, or 1,4-dibromobutane at room temperature resulted in the isolation of tricyclic 1,N2-(1,2-ethano)guanine, 1,N2-(1,3-propano)guanine, or 1,N2-(1,4-butano)guanine products, respectively. O6-Haloalkyl and N1-haloalkyl products were obtained following the use of NaH/1,4-dibromobutane, higher α,ω-dibromoalkanes

Eight new organotin(IV) carboxylates of general formula RnSnL4-n have been synthesized by the reaction of respective organotin(IV) oxide/chloride with stoichiometric amount of the ligand, (E)-2,3-bis(4-chlorophenyl)-2-propenoic acid or its silver salt in dry toluene using Dean and Stark apparatus accordingly. The synthesized carboxylates were characterized using multinuclear (1H, 13C, 119Sn) NMR, FT-IR

A cyanine fluorophore 2-[4-N,N-diphenylaminostyryl]-β-naphthothiazolium propylsulfonate, N3, was synthesized. The asymmetric probe N3 displayed aggregation-induced emission (AIE) characteristic in DMSO/H2O mixtures, whereas it presented twisted intra-molecular charge transfer (TICT) non-emissive state in Dioxane/H2O (Diox/H2O) mixtures. Both the AIE and TICT state could be modulated by proteins, exhibiting

The synthesis of the drug alendronate from γ-aminobutyric acid and phosphorus trichloride/phosphorous acid as the P-reagents is revisited using methanesulfonic acid and sulfolane as solvents and ionic liquids (ILs) as additives according to a novel approach. Besides elaborating efficient synthetic methods with a record yield of up to 80%, the misleading literature data were also clarified. It is a

A series of 3α-hydroxyl-3β-methoxymethyl-5α-pregnan-20-ones 7-15 possessing C-21 hydrophilic substituents were synthesized from the corresponding C21-bromo steroid 6 in 24%-89% yields. The hydrophilic groups include amino group from Delepine reaction, hydroxyl group from the hydrolysis by cesium formate in anhydrous MeOH, and amino acids, hydrazinecarboxamide, piperazine, and imidazolyl from nucleophilic

The synthesis of polymers and polymer additives from renewable biosources is of increasing interest. Products based on biosources offer independence from the uncertainty and fluctuation in petrochemical markets and may offer clear advantages over petrochemical counterparts in terms of toxicity, biodegradability, and environmental impact. Isosorbide is a diether diol available from glucose which may

The synthesis and structural characterization of novel amine-borane adducts of ibuprofen derivatives are presented. The changes of the electron density on the carbonyl and pyridine ring after formation of N→BH3, N→BF3, and N-CH3+ have been confirmed by 1H, 11B, 13C, and 19F NMR, further supported by homonuclear and heteronuclear correlations. Moreover, electrostatic interactions —H+···−F and the nonclassical

A effective amidation reaction of carboxylic acids with various amines promoted by triphenylphosphine oxide and oxalyl chloride under mild and neutral conditions has been developed. The feature of this procedure was the using and recycling of triphenylphosphine oxide at room temperature in 0.5 h. Furthermore a plausible mechanism also be deduced with the help of 31P NMR spectroscopy.

An one-pot approach to benzoxazole ring from 2-aminophenol and aldehydes utilizing molecular sieve as the catalyst have been developed. The new oxidative cyclization reaction excluded the usage of hazardous chemical reagents, transition-metal catalysts, chemical oxidants, or strong acids, and, therefore, reduced the production of toxic chemical waste. This offers an environmentally friendly pathway

Novel 5,5′-disubstituted BMP32C10 derivatives bearing different sized substituents were designed and prepared. The stoichiometries and complexation behavior between these hosts and paraquats were studied. It was found that bulky 5,5′-substituents disfavor complexation with paraquats by hindering the formation of [2]pseudorotaxane and “taco” complexes.

Optically active macrocycles consisting of two P-stereogenic bisphosphine units and two π-conjugated linkers were synthesized via [2 + 2] cyclization. A clear Cotton effect was observed in the π–π* transition region of the π-conjugated units, indicating that the chirality is induced by the P-stereogenic bisphosphine moieties onto the π-conjugated linkers. Compared with model compounds, the orientation

A convenient and efficient regioselective synthesis of phosphorylated 3-(β-hydroxy)allenes by an atom economical [2,3]-sigmatropic rearrangement of the mediated propargyl phosphite or phosphinite which can be readily prepared via reaction of protected 5-(tetrahydro-2H-pyran-2-yloxy)-hex-1-yn-3-ol with dimethyl chlorophosphite or chlorodiphenyl phosphine, respectively, is described. This paper discusses

The various methods of aminomethylation of some PH-acids with proline and their derivatives are investigated. The numerous derivatives of proline and corresponding phosphonates, phosphonites, phosphinates, and phosphorane with proline moieties are presented.

A one-pot four component condensation of isatin, sarcosine, 2-[2-oxo-1-(prop-2-ynyl)indolin-3-ylidene]malononitrile and aryl azides has been reported for the synthesis of novel dispirooxindole pyrrolidine linked 1,2,3-triazole conjugates using Cu(I) as a catalyst in PEG-400 by stereoselective [3 + 2] azide-alkyne cycloaddition followed by [3 + 2] azomethine ylide and alkene cycloaddition. Structures

The synthesis and photophysical properties of a series of phenyleneethynylenes containing a main group element moiety of B, Si, or P on the side chain as a simple model are reported. The HOMO-LUMO energy levels are significantly altered due to a rise of the HOMO level (P) or a lowering of the LUMO level (B and PO) compared with the parent phenyleneethynylene, which is also supported by density functional

The convenient syntheses of new aryl-substituted hydroxymethylphosphonic and methylenediphosphonic acids from the aromatic aldehydes, their derivatives, and phosphorous acid esters in the presence of the effective catalysts (trimethylsilyl trifluoromethanesulfonate, zinc chloride, and cadmium iodide) were developed.

Two novel dithiophosphonate ligands, HS2P(p-C6H4OMe)(OCH2CH2CH(CH3)2) (1) and HS2P(p-C6H4OMe)(OCH(CH3)2) (2), were synthesized and characterized by multinuclear (1H, 31P, and 13C) NMR, infrared spectroscopy as well as elemental analysis. The reactions of 1 and 2 with NiCl2·6H2O and Cd(NO3)2·4H2O in methanol led to novel complexes 3 and 4. The single crystal X-ray structures of 3 and 4 showed tetracoordinated

α-d-Glucofuranose and α-d-allofuranose diacetonides react with 2,4-diorganyl 1,3,2,4-dithiadiphosphetane-2,4-disulfides to form optically active dithiophosphonates in 78–81% yields, which are transformed into the corresponding ammonium salts in 90–97% yields by the treatment of n-hexadecylamine. The S-silyldithiophosphonate was prepared in 93% yield by the reaction of 2,4-bis(butoxyphenyl) 1,3,2,4

Structural aspects of organosilicon(IV) and organotin(IV) complexes with dehydroacetic acid and amino ether Schiff base ligand have been described with the help of elemental analyses, conductance measurements, UV–Vis, infrared, multinuclear magnetic resonance, mass spectroscopy as well as thermogravimetric analysis, and X-ray diffraction studies. Analysis of data suggested that the Schiff base provides

Deoxygenation of 2-nitrodiarylamines by triphenylphosphine is presented as an efficient method for synthesis of 2-(arylamino)aryliminophosphoranes, useful as starting materials in the synthesis of benzannulated nitrogen heterocycles. The reaction is complementary for the known synthesis of aryliminophosphoranes from 2-nitrosodiarylamines giving rise to obtain the title products in the broader scope

Cyclic phosphorus compounds, 6H-dibenz[c,e][1,2]oxaphosphorin-6-oxide derivatives, were efficiently synthesized by the Friedel–Crafts reaction of 2-hydroxybiphenyls with phosphorus trichloride in the presence of superacids, especially trifluoromethanesulfonic acid (TfOH) as a catalyst. TfOH was investigated for the first time as an effective catalyst for the aromatic phosphination of 2-hydroxybiphenyls

As a novel extension, the Kabachnik–Fields reaction was applied to the synthesis of alkyl α-aminomethyl-phenylphosphinates, and the double phospha-Mannich reaction was utilized in the preparation of bis(alkoxyphenylphosphinylmethyl)amines. A total of 27 new aminophosphinate derivatives were synthesized by the microwave-assisted solvent-free condensation of alkyl phenyl-H-phosphinates, paraformaldehyde

The boron dipyrromethene (BODIPY) triads consisting of two triphenylamine units as electron donor (D) and BODIPY core as electron acceptor (A; B3, and B4) have been synthesized using facile palladium cross-coupling reactions to broaden the absorption of the BODIPY dyes. All dyes and intermediates were characterized by 1H NMR, 11B NMR, 13C NMR, and 19F NMR spectroscopies, UV–Vis spectroscopy, fluorescence