4-(3-Dialkylamino-2,5-dioxopyrrolidin-1-yl)benzoic acid esters

Kolyamshin, O. A.; Danilov, V. A.; Kol'tsov, N. I.

doi:10.1134/s1070428007030104

Cited by 14 publications

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“…Maleimide derivatives are known to form alternating copolymer structures with styrene derivatives due to their different monomer reactivities. , A similar approach was used by Morishima et al in methyl methacrylate copolymers of PVMPT , , where the authors had concluded from CV measurements that the phenothiazine units have less interactions than in the homopolymer. Copolymerization of 3-vinyl- N -methylphenothiazine ( 6 ) with N -methylmaleimide ( MM ) and N -( p -(methoxycarbonyl)phenyl)maleimide ( p-MCPM ) (for synthesis, see the Supporting Information , ) under free-radical conditions afforded alternating copolymers P(VMPT- alt -MM) and P(VMPT- alt -p-MCPM) (Scheme ). Analysis by 1 H NMR spectroscopy confirmed a 1:1 ratio of the N -CH 3 (phenothiazine) and CH 3 group of the respective comonomer, underlining the presence of an alternating copolymer (see the Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

“…57,58 A similar approach was used by Morishima et al in methyl methacrylate copolymers of PVMPT, 39,59 where the authors had concluded from CV measurements that the phenothiazine units have less interactions than in the homopolymer. Copolymerization of 3-vinyl-N-methylphenothiazine (6) 23 with N-methylmaleimide (MM) and N-(p-(methoxycarbonyl)phenyl)maleimide (p-MCPM) (for synthesis, see the Supporting Information 60,61 ) under free-radical conditions afforded alternating copolymers P(VMPT-alt-MM) UV/vis/NIR spectra of oxidized samples of P(VMPT-alt-MM) and P(VMPT-alt-p-MCPM) showed reduced intensities of the characteristic bands for the π-dimers (650−950 nm) and pimers (around 1500 nm) compared to PVMPT (Figure 5a,b). This demonstrates that the close proximity of phenothiazine units in the backbone of PVMPT is an ideal prerequisite for πinteractions, which is not given in the alternating copolymers, and that the intramolecular π-interactions play a decisive role in comparison to intermolecular (or interchain) π-interactions in PVMPT, since only the former are suppressed in P(VMPTalt-MM) and P(VMPT-alt-p-MCPM).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Bridging the Gap between Small Molecular π-Interactions and Their Effect on Phenothiazine-Based Redox Polymers in Organic Batteries

Otteny

Perner

Einholz

et al. 2021

ACS Appl. Energy Mater.

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Organic redox polymers are considered a “greener” alternative as battery electrode materials compared to transition metal oxides. Among these, phenothiazine-based polymers have attracted significant attention due to their high redox potential of 3.5 V vs Li/Li+ and reversible electrochemistry. In addition, phenothiazine units can exhibit mutual π-interactions, which stabilize their oxidized states. In poly(3-vinyl-N-methylphenothiazine) (PVMPT), such π-interactions led to a unique charge/discharge mechanism, involving the dissolution and redeposition of the polymer during cycling, and resulted in an ultrahigh cycling stability. Herein, we investigate these π-interactions in more detail and what effect their suppression by molecular design has on battery performance. Our study includes a dimeric reference compound for PVMPT, polymers with bulky tolyl or mesityl substituents on the phenothiazine units to inhibit π-interactions and alternating copolymers with maleimide groups to increase spatial distancing between phenothiazine groups. UV/vis- and electron paramagnetic resonance (EPR)-spectroscopic as well as electrochemical measurements in composite electrodes demonstrate how the unique structure of PVMPT is instrumental in obtaining a high cycling stability in poly(vinylene) derivatives of phenothiazine.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Bridging the Gap between Small Molecular π-Interactions and Their Effect on Phenothiazine-Based Redox Polymers in Organic Batteries

Otteny

Perner

Einholz

et al. 2021

ACS Appl. Energy Mater.

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Section: Methodsmentioning

confidence: 99%

“…The solid was recrystallized from a chloroform/hexane mixture. All compounds 7a [39],7b, c,d [40],7e [41] and 7f [42] were synthesized previously and their data were compared with previous literature. In a 25 mL round-bottom flask, it was added the suitable derivative 4a-e (0.4 mmol), 10 mL of acetone and 0.2 mL of triethylamine (2.7 mmol).…”

Section: Synthesis Of N-aryl Maleimides (7a-f)mentioning

confidence: 99%

Biologically active thio‐pyrimidinones from base‐catalyzed thiol‐ene coupling with maleimides

Feitosa

Maciel

Anjos

2022

Journal of Heterocyclic Chem

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The synthesis of 2‐thiopyrimidinones through thiol‐ene coupling is reported here, resulting in 35 unpublished molecules. Thiopyrimidinones may exhibit one up to three tautomeric forms, and favoring the thiol tautomer is favored is the key to success of this reaction. Five compounds from all obtained products, those substituted with a carbonyl ester portion in the side chain, were chosen to be tested in a preliminary evaluation for human aldose reductase inhibition. All tested compounds showed an inhibition percentage equal to or >60%.

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“…Олардың бірі -белгілі дәрілердің фармакофорты фрагменттері болса, бірі табиғи биологиялық белсенді қосылыстардың құрамына кіреді. Ғылыми деректерден n-аминобензой қышқылының туындылары мен олардың эфирлері -табиғи қосылыстардың синтетикалық аналогтары болатыны, ал пирролидон туындыларының жаңа биологиялық белсенді қосылыстардың синтезін ынталандыратын жоғары гипнозды, антиконвульсантты, антиаритмиялық белсенділігі [4][5] бар екендігі белгілі. Пирролидон ядросы бар n-аминобензой қышқылының жаңа туындыларын алу үшін ультрадыбыстық жағдайда этил 4-(2,5-диоксо-2,5-дигидро-1Нпирролил)бензоаты синтезделді.…”

Section: ультрадыбыс жағдайында 4-аминобензой қышқылының модификациялunclassified

Synthesis of a Modified 4-Aminobenzoic Acid Derivative Under Ultrasound Conditions

Zhakina¹,

Abdrakhmanova

2020

Series Chemistry and Technology

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The search for new effective drugs with biologically active properties is one of the urgent problems. Recently, to intensify the process of their synthesis and increase the efficiency of chemical reactions, wave chemistry has been used. Increased interest of researchers is caused by the synthesis of compounds with biologically active properties using the method of ultrasonic treatment (US). It is known that derivatives of p-aminobenzoic acid and their esters are synthetic analogues of natural compounds, and pyrrolidone derivatives have high hypnotic, anticonvulsant, antiarrhythmic activity, which stimulates the synthesis of new biologically active compounds. In a brief report, the possibility of synthesizing ethyl-4-(2,5-dioxo-2,5-dihydro-1H-pyrrolyl) benzoate from 3-[(4-ethoxycarbonyl) phenylcarbamoyl]-2-propenoic acid using ultrasonic activation through a step is considered disclosure of the furan cycle with further cyclization. Ethyl ester p-aminobenzoic acid and maleic anhydride were used as starting reagents. An ultrasound device IL-100-6/2, equipped with a magnetostrictive transducer, with an operating frequency of 22 kHz, with a maximum power of 1200 W and a cylindrical waveguide, was used as a source of ultrasound. The synthesis of 3-[(4-ethoxycarbonyl) phenylcarbamoyl]-2-propenoic acid was carried out by reacting the starting reagents at equimolar ratios and room temperature. The US time was 10 minutes. The reaction proceeds smoothly. Ultrasound has a significant effect on the rate of chemical reactions and can increase the yield of the final product. Under classical conditions, the synthesis time was 180 minutes; using ultrasound, the synthesis time was reduced by 3 times. The product yield was 92%. The structure and composition of the obtained compound was confirmed by IR- and H1 NMR-spectroscopy. In the IR-spectra of the obtained compound, there are absorption bands of the amide group (NHCO) in the region of 3280, 3190 cm-1, absorption bands of the carbonyl group (C=O), characteristic in the region of 1670 cm-1, absorption band (COC) in the region of 1230 cm-1. The resulting compound, 3-[(4-Ethoxycarbonyl) phenylcarbamoyl]-2-propenoic acid, made it possible to study the step of opening the furan ring, with further cyclization. Ethyl 4-(2,5-dioxo-2,5-dihydro-1H-pyrrolyl) benzoate was obtained in 89% yield by azeotropic distillation of water in the presence of toluenesulfonic acid in a DMFA-toluene mixture. The resulting product is a light yellow powder with melting point 114-115°C. The structure and composition of the obtained compound was confirmed by IR-and H1 NMR-spectroscopy. In the IR-spectra of the obtained compound, the stretching vibrations of the НС=СН group manifest themselves in the form of a low-intensity but characteristic signal at 3100-3090 cm-1, stretching vibrations of the С=О group as intense bands in the region of 1700-1680 cm-1 and a weak overtone at 3465-3450 cm-1, stretching vibrations of the COC group in the region of 1245 cm-1. When analyzing the Н1 NMR-spectrum of a compound, ethyl 4-(2,5-dioxo-2,5-dihydro-1Н-pyrrolyl) benzoate, the signals of aromatic four protons Н1- Н2 (4Нaryl, 3JНН 8 Hz) are recorded in the field of weak fields: H1 doublet at 7.51 ppm. and a doublet at 8.05 ppm. Signals of the ethyl fragment: (3H, CH3, 3JHH 8 Hz), appear as a singlet at 1.43 ppm. and (2H, CH2, 3JHH 8 Hz) quadruplet at 4.34 ppm. The protons of the CH group of the imide cycle (2H, CH=CH) appear as a singlet at 7.11 ppm. Keywords: ultrasound, ethyl ether p-aminobenzoic acid, maleic anhydride, cyclization.

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4-(3-Dialkylamino-2,5-dioxopyrrolidin-1-yl)benzoic acid esters

Cited by 14 publications

References 0 publications

Bridging the Gap between Small Molecular π-Interactions and Their Effect on Phenothiazine-Based Redox Polymers in Organic Batteries

Bridging the Gap between Small Molecular π-Interactions and Their Effect on Phenothiazine-Based Redox Polymers in Organic Batteries

Biologically active thio‐pyrimidinones from base‐catalyzed thiol‐ene coupling with maleimides

Synthesis of a Modified 4-Aminobenzoic Acid Derivative Under Ultrasound Conditions

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