Potassium Phthalimide Research Articles

Potassium Phthalimide Doped with Delta‐Site Structures to Construct Ultra‐Long Cycle Life Aqueous Zn‐Polymer Batteries

AbstractAqueous Zn‐polymer batteries hold great promise for environmentally friendly energy storage systems. However, the poor cycling performance caused by irreversible structural deformation and polymer chain entanglement during the embedding and de‐embedding processes of Zn2+ and H+ ions is one of the key challenges facing their development. Here a new polyaniline cathode doped is developed with potassium phthalimide using a secondary doping approach. This polymeric electrode integrates the conjugated backbone for charge transport with an anionic phthalimide dopant for constructing a triangular‐site structure, as illustrated by the density functional theory calculations. This unique molecular structure is favorable for improving conductivity and structural stability by effectively modulating the localized electron cloud density. The Zn‐polymer battery holds an outstanding capacity retention of 76.1% after 25,000 cycles at a current density of 1 A g−1 with the coulombic efficiency maintained above 99.4%. This secondary doped polymer strategy offers a new host alternative for the ultra‐long cycle life of Zn‐polymer batteries. The molecular design strategy and the insight into the relationship between the structure and performance may provide some guidelines for developing polymer cathodes with high stability.

Simple and Efficient Method for Mono‐ and Di‐Amination of Polypyridine N‐Oxides

AbstractHerein we report a simple synthetic route towards both known and novel aminated polypyridyl ligands. The use of tosyl chloride in combination with potassium phthalimide followed by hydrolysis allows for chemo–selective ortho–amination of (poly)pyridyl mono‐ and di‐N‐oxides with good to excellent yield. The reactions are scalable and reproducible while using inexpensive, commercially available reagents.

Microwave-assisted synthesis of -CF3 functionalized 3,4-dihydropyrimidinone/thione/imine derivatives by using potassium phthalimide (PPI) as a green and reusable organocatalyst and their anti-microbial evaluation

One-pot synthesis of novel -CF3 functional group containing 3,4-dihydropyrimidinone/thione/imine derivatives 8a-l, 9a-l and 10a-l has been successfully performed in high yields through the reaction of aromatic aldehydes, β-dicarbonyl compound, urea/thiourea/guanidine hydrochloride by using potassium phthalimide (PPI) as organocatalyst under solvent-free conditions under microwave irradiation at 300 W. PPI has been introduced as an efficient and biodegradable organocatalyst in Biginelli condensation with excellent reusability. The good yield of products, fast reaction time, simple work-up procedure, as well as usage of nontoxic, reusable, and easily recoverable catalyst under magnetic starring have been counted as advantages of the applied process. This organocatalyst can be removed after completion of reaction and reused several times under the same reaction conditions without significant loss of catalyst activity. The anti-microbial activity of all newly synthesised Biginelli products has been investigated against a variety of microorganisms such as E. coli, S. aureus, S. pyogenes, P. aeruginosa, C. albicans, A. niger and A. clavatus.

Synthesis of New Cyclohexenone Derivatives Using Potassium Phthalimide as a Green Organocatalyst. One-Pot Microwave-Assisted Synthesis and Antimicrobial Evaluation

Synthesis of New Cyclohexenone Derivatives Using Potassium Phthalimide as a Green Organocatalyst. One-Pot Microwave-Assisted Synthesis and Antimicrobial Evaluation

N -Heterocycles Extended π-Conjugation Enables Ultrahigh Capacity, Long-Lived, and Fast-Charging Organic Cathodes for Aqueous Zinc Batteries

<i>N</i> -Heterocycles Extended π-Conjugation Enables Ultrahigh Capacity, Long-Lived, and Fast-Charging Organic Cathodes for Aqueous Zinc Batteries

Polymerization of N-phenylmaleimide Using Different Catalysts

The polymerization of N-phenylmaleimide (N-PMI) employing sodium phosphate tribasic as a catalyst has been successfully investigated in this study. The effect of dimethyl sulfoxide (DMSO) solvent on the principal catalyst, sodium phosphate tribasic, was extensively studied. The effects of several catalysts, including tetrabutylammonium acetate (TBAA), 4-dimethylaminopyridine (DMAP), Benzyl triethylammonium chloride (BTEAC), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1,4-diazabicyclo[2.2.2]octane (DABCO), 1-Methylimidazole (1MA) and potassium phthalimide salt on polymerization of N-PMI have been discussed in this study. Additionally, the kinetics of polymerization in DMSO with Na3PO4 as the initiator is investigated. By using 1H and 13C nuclear magnetic resonance (NMR) spectrum analysis, attenuated total Reflection-Fourier transform infrared (ATR-FTIR), the resultant polymers were identified. Thermogravimetric and differential scanning calorimetric analyses were used to study the thermal behaviors. Our results prove that a salt form of catalyst can initiate the polymerization of N-PMI in dimethyl sulfoxide at a suitable concentration and under favorable conditions.

Practical synthesis of phthalascidin and zalypsis antitumor agents

The first total synthesis of zalypsis and the practical synthesis of phthalascidin (Pt-650) are achieved through the Pictet-Spengler cyclization coupling strategy. The direct iodination of the primary alcohol in trihydroxyl intermediate 26 followed by SN2 reaction with potassium phthalimide is employed to rapidly introduce the required amino functionality at C-22 on the pentacyclic framework. By the approaches, the two antitumor agents can be obtained from sesamol or N-Cbz-l-tyrosine with ca. 8%-10% overall yield.

Green and mild production of 5-aminolevulinic acid from algal biomass

Algal biomass was converted into 5-aminolevulinic acid (5-ALA) in five chemical steps: conversion to 5-(chloromethyl)furfural (5-CMF), ammoniation, ring-opening (photo-oxidation), reduction, and hydrolyzation. Among them, we mainly focused on the 5-CMF production and the following ammoniation. To our knowledge, the mixed solvent catalytic system of deep eutectic solvent (DES) and low concentration hydrochloric acid is the first reported for the synthesis of 5-CMF from algal biomass, providing a 24.6% 5-CMF yield at 120 °C for 5 h. Potassium phthalimide (KPI) was employed as an ammoniation reagent with superb selectivity and activity instead of conventional sodium azide (NaN3). Optimizing the experimental design, a 23.7% 5-ALA yield along with high purity (>96%) was achieved from 5-CMF, and the total 5-ALA yield was 5.8% from algal biomass. This work provides a green and mild pathway for 5-ALA production from algal biomass.

Synthesis of Fatty Acid Methyl Ester Catalyzed by Potassium Phthalimide

Synthesis of Fatty Acid Methyl Ester Catalyzed by Potassium Phthalimide

SYNTHESIS, CRYSTAL STRUCTURE, AND STABILITY OF N-LUPINYLPHTHALIMIDE CONFORMERS

As a result of studying the interaction of chlorolupinine with potassium phthalimide, the optimal synthesis conditions for N-lupinylphthalimide by the Gabriel method are identified. The crystal structure of N-lupinylphthalimide is determined for the first time by single crystal XRD. The energy characteristics are calculated using the quantum chemical method. It is found that the conformer with the chair conformation of the cycles with the axial orientation of the phthalimide substituent is more stable than that with the equatorial orientation.

A Universal Strategy For N‐Doped 2D Carbon Nanosheets With Sub‐Nanometer Micropore For High‐Performance Supercapacitor

Preparing carbon nanosheets with precise control of open porous morphology via universal process and understanding the relationship between structure and capacitive performance are very urgent for achieving advanced supercapacitors. Herein, we propose a simple yet effective additive‐free method to transform a bulk layered potassium phthalimide salt to novel nitrogen‐doped two‐dimensional carbon sheets by self‐activation during calcination. The obtained samples showed large‐sized and flat structure with lateral size around 10 µm, uniform sub‐nanometer micropore size distribution of about 0.65 nm dimension, large specific surface area up to 2276.7 m2 g−1, and suitable nitrogen doping. Benefited from these merits, the optimized sample delivers a high specific capacitance of 345 F g−1 at 1 A g−1 and retains 270 F g−1 even at 50 A g−1 in 6.0 M KOH electrolyte. Remarkably, the symmetric supercapacitor shows maximum energy densities of 16.43Wh kg−1 and 23.6 Wh kg−1 in 6.0 M KOH and 1.0 M Na2SO4 electrolytes, respectively. Importantly, on account the universality and simplicity of this method, the undoped as‐prepared carbon sheet with uniform sub‐nanometer micropore distribution can be synthesized from different potassium‐containing salts with layered structure, which can be employed as a model for a deep understanding the effect of sub‐nanometer micropores on capacitive performances. We find the number of micropores centered at 0.65 nm can be applied as one indicator to clarify the correlation between capacitance and critical pore size below 1 nm.

One-step synthesis of highly porous nitrogen doped carbon from the direct pyrolysis of potassium phthalimide for CO2 adsorption

In the current work, we reported the synthesis of nitrogen doped carbons (NDCs) with a very convenient one-step strategy. Highly porous NDCs were successfully prepared from the direct pyrolysis of potassium phthalimide at 600−900 °C. The obtained carbon had a high specific surface area (2053 m2/g) and pore volume (1.14 cm3/g) after pyrolysis at 900 °C. The nitrogen content of the carbon was 3.3–9.1 wt%, and decreased with the increase of pyrolysis temperature. The combination of high porosity and nitrogen content made the synthesized NDCs attractive CO2 adsorbents. At 25 °C, the carbon exhibited CO2 uptakes of 1.1 mmol/g at 0.15 bar, and 3.4 mmol/g at 1 bar. The experiment results also revealed a linear relationship between the uptake at 0.15 bar and the CO2/N2 adsorption selectivity. Small micropores and nitrogen containing functionalities had decisive effects on these properties.

8,18-Dithia-1,4,11,14-tetraazapentacyclo[11.7.0.03,11.05,9.015,19]icosa-3,5(9),6,13,15(19),16-hexaene-10,20-dione

4H-3λ2-Thieno[3,2-d]pyrimidin-4-one derivatives are of interest as biologically active compounds. In this communication, 2-(chloromethyl)-4H-3λ2-thieno[3,2-d]pyrimidin-4-one (1) was investigated in the reaction with ammonia, potassium phthalimide, and other basic agents. The dimerization product—8,18-dithia-1,4,11,14-tetrazapentacyclo[11.7.0.03,11.05,9.015,19]icosa-3,5(9),6,13,15(19),16-hexaene-10,20-dione was formed in the reaction with potassium phthalimide in DMF, by heating at 110 °C for 5 h. The structure of the newly synthesized compound was established by means of elemental analysis, high resolution mass-spectrometry, 1H, 13C NMR, and IR spectroscopy, and mass-spectrometry.

Correction to “One-Pot and Efficient Synthesis of 5-Aminopyrazole-4-carbonitriles Catalyzed by Potassium Phthalimide”: HETEROCYCLES, 2017, 94, 276, DOI: 10.3987/COM-16-13623

Correction to “One-Pot and Efficient Synthesis of 5-Aminopyrazole-4-carbonitriles Catalyzed by Potassium Phthalimide”: HETEROCYCLES, 2017, 94, 276, DOI: 10.3987/COM-16-13623

Gabriel Synthesis of Hexakis(aminomethyl)benzene and Its Derivatization

AbstractHexakis(aminomethyl)benzene, which is a key precursor for various hexa‐substituted functional molecules, was synthesized by Gabriel synthesis. Nucleophilic substitution of hexakis(bromomethyl)benzene with potassium phthalimide gave hexakis(phthalimidemethyl)benzene in excellent yield. Hydrazinolysis of the phthalimide moieties of hexakis(phthalimidemethyl)benzene afforded a mixture of hexakis(aminomethyl)benzene and 2,3‐dihydrophthalazine‐1,4‐dione. Pure hexakis(aminomethyl)benzene was isolated as its hexahydrochloride upon treating the mixture with HCl. Hexakis‐amides and hexakis‐tosylamide were prepared from hexahydrochloride of hexakis(aminomethyl)benzene in good to high yields. Alkyl‐substituted hexakis‐amide shows extremely high solubility in non‐polar organic solvents like chloroform and n‐hexane. Density functional theory calculation of the structure of hexakis‐amide show that all substituents were oriented to the same side (aaaaaa conformation) via intramolecular hydrogen bonding.

Imide arylation with aryl(TMP)iodonium tosylates.

Herein, we describe the synthesis of N-aryl phthalimides by metal-free coupling of potassium phthalimide with unsymmetrical aryl(TMP)iodonium tosylate salts. The aryl transfer from the iodonium moiety occurs under electronic control with the electron-rich trimethoxyphenyl group acting as a competent dummy ligand. The yields of N-aryl phthalimides are moderate to high and the coupling reaction is compatible with electron-deficient and sterically encumbered aryl groups.

Synthesis and piezoelectric properties of N-phthaloylglutamic acid derivatives

The (S,S)- and (R,R)-enantiomers of dimethyl 2,4-diphthalimidoglutarate were synthesized by nucleophilic substitution of bromine in dimethyl (2S,4RS)-4-bromo-N-phthaloyl-glutamate upon treatment with potassium phthalimide, followed by separation. The crystal structure of the obtained compounds was studied by X-ray diffraction. Crystals of enantiomerically pure dimethyl 4-hydroxy- and 4-phthalimido-N-phthaloylglutamates were found to possess a noticeable piezoelectric activity.

Reactivity of (1-methoxycarbonylpentadienyl)iron(1+) cations with hydride, methyl, and nitrogen nucleophiles

The reaction of tricarbonyl and (dicarbonyl)triphenylphosphine (1-methoxycarbonyl-pentadientyl)iron(1+) cations 7 and 8 with methyl lithium, NaBH3CN, or potassium phthalimide affords (pentenediyl)iron complexes 9a-c and 11a-b, while reaction with dimethylcuprate, gave (E,Z-diene)iron complexes 10 and 12. Oxidatively induced-reductive elimination of 9a-c gave vinylcyclopropanecarboxylates 17a-c. The optically active vinylcyclopropane (+)-17a, prepared from (1S)-7, undergoes olefin cross-metathesis with excess (+)-18 to yield (+)-19, a C9C16 synthon for the antifungal agent ambruticin. Alternatively reaction of 7 with methanesulfonamide or trimethylsilylazide gave (E,E-diene)iron complexes 14d and e. Huisgen [3 + 2] cyclization of the (azidodienyl)iron complex 14e with alkynes afforded triazoles 25a-e.

Potassium Phthalimide (PPI): An Efficient and Green Organocatalyst for the One-pot Synthesis of 6-amino-1,4-dihydropyrano[2,3-c]-pyrazole-5- carbonitrile Derivatives under Microwave Irradiation

Potassium Phthalimide (PPI): An Efficient and Green Organocatalyst for the One-pot Synthesis of 6-amino-1,4-dihydropyrano[2,3-c]-pyrazole-5- carbonitrile Derivatives under Microwave Irradiation

One-Pot and Efficient Synthesis of 5-Aminopyrazole-4-carbonitriles Catalyzed by Potassium Phthalimide

One-Pot and Efficient Synthesis of 5-Aminopyrazole-4-carbonitriles Catalyzed by Potassium Phthalimide