One-pot synthesis of functionalized 4-oxo-2-thioxo-1,3-thiazinanes from primary amines,CS2, and itaconic anhydride

An efficient synthesis of 2-(3-alkyl-4-oxo-2- thioxo-1,3-thiazinan-5-yl)acetic acids is described via a three-component reaction between primary amines, CS₂, and itaconic anhydride.     

Three-component reactions of isocyanides, dialkyl acetylenedicarboxylates, and trans-cinnamoyl chlorides for the synthesis of highly functionalized 2-vinyl furans

Abstract  

In this study, we present a convenient and efficient method for the synthesis of novel, highly substituted 2-vinyl furans using a three-component reaction. The zwitterions generated from the reaction of isocyanides and dialkyl acetylenedicarboxylates are reacted with trans-cinnamoyl chlorides to produce the desired products in good yields.     

A regiospecific synthesis of both positional isomers of 4,6-disubstituted 2-dicyanomethylene-1, 2-dihydropyridin- 3-carbonitriles

A protocol allowing the regiospecific synthesis of both positional isomers of 4,6-disubstituted 2-dicyanomethylene-1,2-dihydropyridin-3-carbonitriles, precursors of 1,6-naphthyridines, is presented. Thus, treatment of enaminoketones with the propanedinitrile dimer yields one regioisomer while the treatment of the corresponding (3-chloro-allylidene)-dimethylammonium perchlorates (easily obtained from enaminoketones and POCl₃), in which the nature of the reactive centers is inverted with respect to the enaminoketone, yields the other regioisomer.     

FeF3-mediated tandem annulation: a highly efficient one-pot synthesis of functionalized N-methyl-3-nitro-4H-pyrimido [2, 1-b] [1, 3] benzothiazole-2-amine derivatives under neat conditions

Molecular Diversity - A straight forward and highly efficient one-pot annulation of 2-aminobenzothiazole, (E)-N-methyl-1-(methylthio)-2-nitroethenamine, and aldehydes in the presence of FeF3 is...     

A simple approach to the synthesis of highly functionalized pyrrole derivatives

The reaction of dibenzoylacetylene and enaminocarbonyl compounds leads to 3-alkylidene-2,3-dihydro-1H-pyrrol-2-ol derivatives in nearly quantitative yields. The reaction of this heterocyclic system with alcohols in the presence of a catalytic amount of HCl produces highly functionalized pyrroles in good yields.     

Ring opening cross-metathesis on solid support: a combinatorial library synthesis of highly functionalized cyclopentanes

Ruthenium catalyzed ring opening cross-metathesis of resin-bound bicyclic alkenes with terminal aryl olefins was utilized for the construction of a combinatorial library containing highly functionalized cyclopentane derivatives. The technology described herein represents a convergent method for the diastereospecific synthesis of unique cyclopentane molecular scaffolds useful for exploratory medicinal chemistry. This revised version was published online in August 2006 with corrections to the Cover Date.     

One-pot synthesis of single-crystalline Cu2O hollow nanocubes

Single-crystalline Cu₂O hollow nanocubes have been successfully synthesized via a simple wet chemical route in the absence of any surfactants or templates. By studying the growth process of the Cu₂O hollow nanocubes, we found that the Cu₂O hollow nanocubes were formed through a reducing and simultaneously etching process. The speed of reducing Cu(OH)₂ into Cu₂O was much faster than the speed of etching Cu₂O. As a result, Cu₂O solid nanocubes were firstly formed, and then the solid nanocubes were gradually etched into hollow nanocubes.     

One-pot synthesis of highly fluorescent amino-functionalized graphene quantum dots for effective detection of copper ions

In this work, a green and simple one-pot route was developed for the synthesis of highly fluorescent amino-functionalized graphene quantum dots (a-GQDs) via hydrothermal process without any further modification or surface passivation. We synthesized the a-GQDs using glucose as the carbon source and ammonium as a functionalizing agent without the use of a strong acid, oxidant, or other toxic chemical reagent. The as-obtained a-GQDs have a uniform size of 3–4 nm, high contents of amino groups, and show a bright green emission with high quantum yield of 32.8%. Furthermore, the a-GQDs show effective fluorescence quenching for Cu²⁺ ions which can serve as effective fluorescent probe for the detection of Cu²⁺. The fluorescent probe using the obtained a-GQDs exhibits high sensitivity and selectivity toward Cu²⁺ with the limit of detection as low as 5.6 nM. The mechanism of the Cu²⁺ induced fluorescence quenching of a-GQDs can be attributed to the electron transfer by the formation of metal complex between Cu²⁺ and the amino groups on the surface of a-GQDs. These results suggest great potential for the simple and green synthesis of functionalized GQDs and a practical sensing platform for Cu²⁺ detection in environmental and biological applications.     

Microwave-assisted one-pot multi-component reaction: synthesis of novel and highly functionalized 3-(pyranyl)- and 3-(dihydropyridinyl)indole derivatives

One-pot multi-component reaction of 3-cyanoacetyl indole, aromatic aldehydes and ethyl acetoacetate in the presence of \(\hbox {InCl}_{3}/\hbox {NH}_{4}\) OAc under microwave irradiation for 2–7 min afforded novel and highly functionalized 3-(pyranyl)- and 3-(dihydropyridinyl)indole derivatives, respectively, in good yield.     

One-pot synthesis of benzochromeno-pyrazole derivatives

Abstract  

One-pot synthesis of different benzochromeno-pyrazole derivatives has been reported via reaction of aldehydes, 3-methyl-1H-pyrazol-5(4H)-one and α-naphthol/β-naphthol in the presence of sulfamic acid.     

Tandem synthesis of highly functionalized pyrazole derivatives from terminal alkynes, sulfonyl azides, diethyl azadicarboxylate, and sodium arylsulfinates

The reaction between ketenimine intermediates [generated from terminal alkynes and sulfonyl azides], diethyl azadicarboxylate, and sodium arylsulfinates in N, N-dimethylformamide at room temperature, affords ethyl 2,3-dihydro-3-oxo-4-phenyl-2-tosyl-5-(tosylamino)pyrazole-1-carboxylates in moderate-to-good yields. When diisopropyl azadicarboxylate was used as the ester component, diisopropyl 1-arylsulfonyl-2-{[aryl(alkyl)sulfonyl]-2-phenylethanimidoyl}-1,2-hydrazinedicarboxylates were obtained.     

Zinc triflate: a highly efficient reusable catalyst in the synthesis of functionalized quinolines via Friedlander annulation

An environmentally friendly and highly efficient procedure for the preparation of quinolines and fused polycyclic quinolines has been developed by a simple Friedlander annulation reaction of 2-aminoaryl ketone with carbonyl compounds in presence of zinc triflate under microwave irradiation and solvent-free conditions. The reaction also proceeds effectively when In(OTf)₃ was used in lieu of Zn(OTf)₂ as the catalyst. The catalyst can be recovered after the reaction and reused efficiently in subsequent runs.     

An efficient protocol for the synthesis of 2-amino-4,6-diphenylpyridine-3-carbonitrile using ionic liquid ethylammonium nitrate

Chalcones on condensation with malononitrile and ammonium acetate in the presence of ionic liquid ethylammonium nitrate affords the corresponding 2-amino-4, 6-diphenylpyridine-3-carbonitrile in excellent yield. The ionic liquid is recycled and reused several times.     

Ultrasonic-assisted synthesis of highly dispersed MoO3 nanospheres using 3-mercaptopropyltrimethoxysilane

With ultrasonic irradiation as assistance, highly dispersed MoO(3) nanospheres were synthesized using silane coupling agent 3-mercaptopropyltrimethoxysilane HS-(CH(2))(3)Si(OCH(3))(3) (MPTS) as figuration agent. The results of X-ray powder diffractometer (XRD) showed that the precursor was hexagonal molybdenum oxide hydrate (MoO(3).0.55H(2)O). It was converted into orthorhombic MoO(3) after annealed at 400 degrees C for 2h. Transmission electron microscopy (TEM) showed that MoO(3).0.55H(2)O and MoO(3) nanoparticles were spherical with particle-size distribution of ca. 30-80 nm and 25-75 nm, respectively. Results indicated that MPTS and ultrasonic irradiation played important role in formation of highly dispersed MoO(3) nanospheres. X-ray photoelectron spectroscopy (XPS) was also adopted to confirm the growth mechanism. The possible cause of formation was based on dispersion function of ultrasonic irradiation and figuration of MPTS.     

An efficient three-component synthesis of highly functionalized tetrahydroacenaphtho[1,2-b]indolone derivatives catalyzed by L-proline

An efficient and diastereoselective synthetic procedure for highly functionalized tetrahydroacenaphtho[1,2- \(b\) ]indolone derivatives was successfully developed by the three-component reaction of acenaphthequinone, enaminones, and barbituric acid in the presence of a catalytic amount of L-proline. This method has the advantages of convenient operation, excellent yields, mild reaction conditions, and environmental friendliness.     

One-pot multicomponent synthesis of two novel thiolactone scaffolds

We designed two novel thiolactone scaffolds. Both scaffolds can be accessed by a convergent Ugi multicomponent reaction (MCR) and are, thus, amenable to library synthesis. Design, stereoselectivity, structures, full experimental details, and virtual libraries will be reported.     

Acid functionalized,highly dispersed carbonaceous spheres: an effective solid acid for hydrolysis of polysaccharides

Highly dispersed carbonaceous spheres with sulfonic acid groups were successfully prepared from glucose by hydrothermal method. Transmission electron microscopy (TEM) showed the as-synthesized carbonaceous materials were uniform, spherical in shape with an average diameter of about 450 nm. Fourier transform infrared (FT-IR) proved that –SO₃H, –COOH, OH groups were grafted on the surface of the carbonaceous spheres during the sulfonation. Interestingly, the functionalized carbonaceous spheres exhibited high dispersibility in the polar solvent due to the hydrophilic groups on the surface. The mechanism of the formation for the carbonaceous spheres was also discussed based on the analysis of structure and composition. At last, the functionalized carbonaceous spheres were employed as solid acid to hydrolyze starch and cellulose. By comparison, the as-synthesized catalyst showed considerable high yield of glucose.