Tetrabutylammonium bromide (TBAB): a neutral and efficient catalyst for the synthesis of biscoumarin and 3,4-dihydropyrano[c]chromene derivatives in water and solvent-free conditions

A simple, efficient and ecofriendly procedure has been developed using tetrabutylammonium bromide as catalyst for the synthesis of biscoumarin and dihydropyrano[c]chromene derivatives in water and solvent-free neat conditions. The present methodology offers several advantages such as excellent yields, short reaction time and environmentally benign milder reaction conditions.     

以淀粉溶液为催化剂锅三组分法合成四氢苯并[b]吡喃和3,4-二氢吡喃并[c]苯并吡喃衍生物简

Tetrahydrobenzo[b]pyran and 3,4-dihydropyrano[c]chromene derivatives were synthesized via a one-pot three-component condensation of aromatic aldehydes with malononitrile and dimedone or 4-hydroxycoumarin in excellent yields in the presence of starch solution as a highly efficient homogenous catalyst. The use of a nontoxic and biodegradable catalyst, simple work-up procedure, and short reaction time are advantages of this method.     

Synthesis of new heterocycles. 3,4-dihydropyrano[2,3,4-hi]indolizine and derivatives

Interaction of the lithium derivative of 2,3-dihydro-4H-pyrano[3,2-b]pyridine with the diethyl acetal of bromoacetaldehyde, followed by hydrolysis and subsequent ring closure afforded the novel heterocycle 3,4-dihydropyrano[2,3,4-hi]indolizine which was inacessible by the Tschitschibabin method. However, the 2-phenyl derivative was easily prepared by the Tschitschibabin method.     

‘On water’ synthesis of 2,4-diaryl-2,3-dihydro-1,5-benzothiazepines catalysed by sodium dodecyl sulfate (SDS)

An efficient synthesis of 1,3-diaryl-2,3-dihydro-1,5-benzothiazepines has been developed by the reaction of various 1,3-diaryl-2-propenones with 2-aminothiophenol in water under neutral conditions catalysed by SDS. Excellent chemoselectivity was observed for substrates possessing halogen atoms or nitro/alkoxy/thioalkyl groups which did not undergo competitive aromatic nucleophilic substitution of the halogen atoms or the nitro group, reduction of the nitro or the α,β-unsaturated carbonyl group, or dealkylation of the alkoxy/thioalkoxy groups.     

Novel and efficient catalysts for the one-pot synthesis of 3,4-dihydropyrano[c]chromene derivatives in aqueous media

Diammonium hydrogen phosphate, (NH₄)₂HPO₄(DAHP), efficiently catalyzes the one-pot, three-component reaction of an aromatic aldehyde, malononitrile and 4-hydroxycoumarin in aqueous media under mild conditions at room temperature, to afford the corresponding dihydropyrano[c]chromenes in high yields. (S)-Proline has also been used as another neutral catalyst for this reaction at reflux.     

Nano-copper chromite (nano-CuCr2O4): a novel and efficient catalyst for the synthesis of biscoumarin and pyrano[c]chromene derivatives in water at room temperature

Research on Chemical Intermediates - A clean, efficient and eco-friendly procedure has been developed using nano-copper chromite (nano-CuCr2O4) as catalyst for the synthesis of biscoumarin and...     

The condensation of active methylene reagents with salicylaldehyde: Novel synthesis of chromene,azaanthracene, pyrano[3,4‐c]chromene and chromeno[3,4‐c]pyridine derivatives

On heating of the cyanoacetic acid cyclopentylidene hydrazide 1 with salicylaldehyde in the presence of bases the azaanthracene derivative 6 was formed. Also, reaction of 3 with malononitrile and ketones 10a,b afforded the pyrano[3,4‐c]chromene 9 and chromeno[3,4‐c]pyridine 11 respectively. A mechanism for these reactions is proposed.     

Computational studies on the behavior of sodium dodecyl sulfate (SDS) at TiO2(rutile)/water interfaces

Molecular dynamics simulations to study the behavior of an anionic surfactant close to TiO(2) surfaces were carried out where each surface was modeled using three different crystallographic orientations of TiO(2) (rutile), (001), (100) and (110). Even though all three surfaces were made with the same atoms the orientation was a key to determine adsorption since surfactant molecules aggregated in different ways. For instance, simulations on the surface (100) showed that the surfactant molecules formed a hemicylinder structure whereas the molecules on the surface (110) were attached to the solid by forming a hemisphere-like structure. Structure of the aggregated molecules and surfactant adsorption on the surfaces were studied in terms of tails and headgroups density profiles as well as surface coverage. From density profiles and angular distributions of the hydrocarbon chains it was possible to determine the influence of the solid surface. For instance, on surfaces (100) and (001) the surfactant molecules formed molecular layers parallel to the surface. Finally, it was found that in the solids (100) and (110) where there are oxygen atoms exposed on the surface the surfactant molecules were attached to the surfaces along the sites between the lines of these oxygen atoms.     

Ni(II)-Schiff base/SBA-15: a nanostructure and reusable catalyst for one-pot three-component green synthesis of 3,4-dihydropyrano[3,2-c]chromene derivatives

Research on Chemical Intermediates - An efficient, rapid, and environmentally benign Ni(II)-Schiff base/SBA-15-catalyzed one-pot three-component cyclocondensation process was described via the...     

Synthesis of Structurally Diversified Benzo[c]chromene Derivatives under (An)aerobic Conditions Catalyzed by CuI

2‐Bromobenzoic acids underwent an α‐arylation with cyclohexane‐1,3‐diones to give 1H‐benzo[c]chromene‐1,6(2H)‐diones under Ar atmosphere catalyzed by CuI/l ‐proline in the presence of Cs₂CO₃. The subsequent regioselective oxidation took place under O₂ balloon automatically based on the substituents for the construction of structurally diversified benzo[c]coumarin derivatives.     

Computer studies on the effects of long chain alcohols on sodium dodecyl sulfate (SDS) molecules in SDS/dodecanol and SDS/hexadecanol monolayers at the air/water interface

Molecular dynamics simulations of sodium dodecyl sulfate (SDS)/dodecanol and SDS/hexadecanol monolayers at the air/water interface were investigated where the monolayer mixtures were prepared by two different configurations. In the first configuration, all of the dodecanol (or hexadecanol) molecules were placed together and also the SDS molecules were placed together in the surface area. In the second configuration, the dodecanol (or hexadecanol) molecules were uniformly distributed with the SDS molecules, forming a homogeneous mixture. The results showed that the alcohol tails are more ordered and thicker than the SDS tails in monolayers where the alcohol molecules are close to each other and separated from the SDS. However, the reverse trend is observed in monolayers where the SDS and alcohol molecules are well mixed; that is, the alcohol tails seem to have less order. Studies of how the SDS tails are affected by the presence of long chain alcohols are also discussed. Basically, by increasing the alcohol chain length, the order and the thickness of the SDS tails increased when those molecules were placed all together in a region of the surface area. When both surfactants were well mixed, the order and thickness of the SDS chains decreased as the alcohol chain length increased. Comparisons of the present results with actual experiments of similar systems were performed, and they showed similar tendencies.     

Separation of proteins by consecutive sodium dodecyl sulfate (SDS)-polyacrylamide gel electrophoresis and reversed phase high performance liquid chromatography

A procedure for the preparative separation of proteins was developed by using consecutively sodium dodecyl sulfate (SDS)-polyacrylamide gel electrophoresis (SDS-PAGE) and reversed phase high performance liquid chromatography (HPLC). The proteins were separated by SDS-PAGE and afterwards extracted from the gel. The extracted proteins were separated from SDS and other small molecular weight contaminants on a Fractogel TSK HW-40 (F) column in acidic aqueous acetonitrile. The proteins eluted from the Fractogel column were fractionated by HPLC. The identity and purity of the recovered proteins was confirmed by SDS-PAGE analysis.     

Interfacial tension of ethylene and aqueous solution of sodium dodecyl sulfate (SDS) in or near hydrate formation region

The interfacial tensions between ethylene and an aqueous solution of SDS were measured using the pendant-drop method at 274.2 and 278.2 K and in the pressure range from 0.1 to 3.1 MPa, including hydrate formation points. The concentrations of sodium dodecyl sulfate (SDS) aqueous solution were 0, 100, 300, 500, 600, 700, 800, 900, and 1000 ppm. The effects of pressure on the critical micelle concentration (CMC) and the surface excess concentration were studied. It was demonstrated that both the CMC and the saturated surface excess concentration decreased with the increase of pressure.     

Synthesis of furazano[3,4-b]pyrazine derivatives

Various furazano [3, 4-b] pyrazine derivatives were synthesized by condensation of 3, 4-diaminofurazan with substituted phenylglyoxals, cyclic di- and triketones, and diethyl acetylenedicarboxylate.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 613–615, May, 1978.     

Study of the adsorption of sodium dodecyl sulfate (SDS) at the air/water interface: targeting the sulfate headgroup using vibrational sum frequency spectroscopy

The surface sensitive technique vibrational sum frequency spectroscopy (VSFS), has been used to study the adsorption behaviour of SDS to the liquid/vapour interface of aqueous solutions, specifically targeting the sulfate headgroup stretches. In the spectral region extending from 980 to 1850 cm(-1), only the vibrations due to the SO(3) group were detectable. The fitted amplitudes for the symmetric SO(3) stretch observed at 1070 cm(-1) for the polarization combinations ssp and ppp, were seen to follow the adsorption isotherm calculated from surface tension measurements. The orientation of the sulfate headgroup in the concentration range spanning from 1.0 mM to above the critical micellar concentration (c.m.c.) was observed to remain constant within experimental error, with the pseudo-C(3) axis close to the surface normal. Furthermore, the effect of increasing amounts of sodium chloride at SDS concentrations above c.m.c. was also studied, showing an increase of approximately 12% in the fitted amplitude for the symmetric SO(3) stretch when increasing the ionic strength from 0 to 300 mM NaCl. Interestingly, the orientation of the SDS headgroup was also observed to remain constant within this concentration range and identical to the case without NaCl.     

Synthesis of pyrano[3,4-c]pyrazole and pyrazolo[3,4-d][1,2]diazepine derivatives

By the action of thionyl chloride on 3(5)-R-4-phenacylpyrazole-5(3)-carboxylic acid ( 3c,d ), 3-R-5-phenylpyrano[3,4-c]pyrazole-7-(1H)ones ( 4c,d ) were obtained. When 4c,d were treated with hydrazine hydrate followed by refluxing in ethanol containing acetic acid, 4,7-dihydro-3-R-5-phenylpyrazolo[3,4-d][1,2]-diazepin-8-(1H)ones ( 6c,d ) were formed. Compounds 6c,d , in turn, were refluxed in ethanol saturated with hydrochloric acid to yield 6-amino-1,6-dihydro-3-R-5-phenyl-7H-pyrazolo[3,4-c]pyridin-7-ones ( 7c,d ). Compounds 7c,d could be obtained directly from 5c,d. The starting materials 3c,d were prepared by hydrolysis of the oxime of 3(5)-R-4-phenacyl-5(3)carboalcoxypyrazoles ( 1a,b ). Structural assignments rested on correct elemental analysis, molecular weights determined by mass spectrometry, and spectroscopic evidence.     

Poly(3,4-ethylene-dioxythiophene) electrode for the selective determination of dopamine in presence of sodium dodecyl sulfate

A novel biosensor using poly(3,4-ethylene dioxythiophene) (PEDOT) modified Pt electrode was developed for selective determination of dopamine (DA) in presence of high concentrations of ascorbic acid (AA) and uric acid (UA) with a maximum molar ratio of 1/1000, and 1/100 in the presence of sodium dodecyl sulfate (SDS). SDS forms a monolayer on PEDOT surface with a high density of negatively charged end directed outside the electrode. The electrochemical response of dopamine was improved by SDS due to the enhanced accumulation of protonated dopamine via electrostatic interactions. The common overlapped oxidation peaks of AA, UA and DA can be resolved by using SDS as the DA current signal increases while the corresponding signals for AA and UA are quenched. The use of SDS in the electrochemical determination of dopamine using linear sweep voltammetry at modified electrode PEDOT/Pt resulted in detecting dopamine at relatively lower concentrations. The DA concentration could be measured in the linear range of 0.5 to 25 μmol L^? 1 and 30 μmol L^? 1 to 0.1 mmol L^? 1 with correlation coefficients of 0.998 and 0.993 and detection limits 61 nmol L^? 1 and 86 nmol L^? 1, respectively. The validity of using this method in the determination of dopamine in human urine was also demonstrated.