Dione Derivatives Research Articles

PTSA-catalyzed four-component domino reactions for the one-pot synthesis of functionalized 11H-benzo[a]benzo[6,7]chromeno[2,3-c]phenazine-11,16(17H)-diones in PEG

An efficient p-toluenesulfonic acid catalyzed synthesis of 11H-benzo[a]benzo[6,7]chromeno[2,3-c]phenazine-11,16(17H)-dione derivatives has been described by one-pot, four-component condensation of 2-hydroxynaphthalene-1,4-dione, o-phenylenediamine, aromatic aldehydes using polyethylene glycol as solvent. This domino protocol produces biologically considerable heterocycles with the formation of C–C, C=C, C–N, C=N, C–O bonds in a single operation and this efficient green process provides significant advantages such as: operational simplicity, easy work-up procedure, high yields, avoidance of hazardous or toxic catalysts and organic solvents, and is devoid of inessential derivatization and generation of hazardous substances.

Synthesis of new hexahydro-1H-isoindole-1,3(2H)-dione derivatives from 2-ethyl/phenyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3-(2H)-dione

A new and appropriate synthesis for hexahydro-1H-isoindole-1,3(2H)-dione derivatives has been developed starting from 3-sulfolene. The epoxidation of 2-ethyl/phenyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3-(2H)-dione and then the opening of the epoxide with nucleophiles gave hexahydro-1H-isoindole-1,3(2H)-dione derivatives. Amino and triazole derivatives of hexahydro-1H-isoindole-1,3(2H)-dione were synthesized from the formed product by the opening reaction of the epoxide with sodium azide. Hydroxyl analogues were obtained from cis-hydroxylation of 2-ethyl/phenyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3-(2H)-dione. The hydroxyl groups were converted to acetate.

1603966: Copper-catalysed couplings of N-substituted-N-methacryloylbenzamides with isopropanol to generate hydroxyl-substituted isoquinoline-1,3(2H,4H)-dione derivatives – ESI

1603966: Copper-catalysed couplings of N-substituted-N-methacryloylbenzamides with isopropanol to generate hydroxyl-substituted isoquinoline-1,3(2H,4H)-dione derivatives – ESI

ChemInform Abstract: Synthesis of Optically Pure Spiro[cyclohexane‐oxindoline] Derivatives via Catalytic Asymmetric Diels—Alder Reaction of Brassard‐Type Diene with Methyleneindolines.

A highly efficient N,N′-dioxide–Zn(II) complex catalytic system for the asymmetric Diels–Alder reaction of Brassard-type diene with methyleneindolines was developed. The optically pure spiro[cyclohex[3]ene-1,3′-indoline]-1′-carboxylate-2, 2′-dione derivatives containing three stereocenters were obtained in moderate yields with 98% to >99% ee in a stereospecific manner.

Efficient Catalyst One-Pot Synthesis of 7-(Aryl)-10,10-dimethyl-10,11-dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-dione Derivatives Complemented by Antibacterial Activity

The problem of bacteria resistance to many known agents has inspired scientists and researchers to discover novel efficient antibacterial drugs. Three rapid, clean, and highly efficient methods were developed for one-pot synthesis of 7-(aryl)-10,10-dimethyl-10,11-dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-dione derivatives. Three components are condensed in the synthesis, 4-hydroxycoumarin, 5,5-dimethyl-1,3-cyclohexanedione, and aromatic aldehydes, using tetrabutylammonium bromide (TBAB), diammonium hydrogen phosphate (DAHP), or ferric chloride (FeCl3), respectively. Each method has different reaction mechanisms according to the catalyst. The present methods have advantages, including one-pot synthesis, excellent yields, short reaction times, and easy isolation of product. All catalysts utilized in our study could be reused several times without losing their catalytic efficiency. All synthesized compounds were fully characterized and evaluated for their antibacterial activity.

Nano-ferrite supported glutathione as a reusable nano-organocatalyst for the synthesis of phthalazine-trione and dione derivatives under solvent-free conditions

Nano-organocatalyzed one-pot four-component reactions for the synthesis of phthalazine-trione/dione derivatives have been devised for the first time from easily accessible starting materials under solvent-free conditions.

An efficient synthesis of sulfonated quinoline diones by copper catalyzed sulfonylation of activated alkenes with sulfonylhydrazides

A novel and highly efficient cascade synthesis of sulfonated quinoline dione derivatives from N-(2-cyanoaryl) methylacrylamides and sulfonylhydrazides in good yields is described.

An approach to design antimicrobial agents by 2D QSAR studies on series of 5, 5-diphenylimidazolidine-2, 4-dione derivatives

A series of twenty two molecules substituted 5,5-diphenylimidazolidine-2,4-dione derivatives displaying variable inhibition of microbial activity were selected to develop models for establishing 2D QSAR by multiple linear regression analysis. The compounds in the selected series were characterized by spatial, molecular and electro topological descriptors using QSAR model of molecular design suite (V-Life MDS 3.5). Correlations between inhibitory activities and calculated predictor variables were established through multiple linear regression method. The whole dataset was divided into training set (17 compounds) and test set (05 compounds). The statistically significant best 2D QSAR model having correlation coefficient r 2 = 0.8686 and cross validated squared correlation coefficient q 2 = 0.7994 with external predictive ability of pred_r 2 = 0.6791 coefficient of correlation of predicted data set (pred_r 2 se) 0.0999 was developed by stepwise MLR method with the descriptors like SSCH 3 , SdSE-index, SsssN Count and Xlogp. These results should serve as a guideline in designing more potent and selective antimicrobial and antifungal molecules.

Synthesis of 10‐substituted 3,6‐Diphenyl‐9‐aryl‐3,4,6,7,9,10‐hexahydro‐acridine‐1,8(2H,5H)‐dione Derivatives and Biological Activities

A series of novel 10‐substituted 3,6‐diphenyl‐9‐aryl‐3,4,6,7,9,10‐hexahydroacridine‐1,8(2H,5H)‐dione derivatives 2 were synthesized by condensation of compounds 1 with amines, which the compounds 1 were synthesized by 5‐phenylcyclohexane‐1,3‐dione and aromatic aldehydes according to Knoevenagel, Michael, and cyclization reactions in the presence of a very small amount of l‐proline as catalyzed at room temperature. The structures of all the synthesized compounds were characterized by IR, 1H NMR, and MS. In addition, the molecular structures of compound 1a have been determined by single‐crystal X‐ray diffraction analysis.

A new, one-pot, efficient method for the synthesis of 5-methyl-3H,3′H-spiro[furan-2,1′-isobenzofuran]-3,3′-dione derivatives in water

A simple and efficient procedure for the synthesis of 5-methyl-3,3′-dioxo-3H,3′H-spiro[furan-2,1′-isobenzofuran]-3,3′-dione derivatives, proceeding via a condensation reaction between ninhydrin and various 1,3-dicarbonyl compounds followed by oxidative cleavage of the corresponding 3a,8b-dihydroxy-2-methyl-4-oxo-4,8b-dihydro-3aH-indeno[1,2-b]furans is presented. The syntheses were carried out in water at room temperature and proceeded with short reaction times to give the products with high yields. The structural assignments were supported by IR, 1H NMR, 13C NMR, and mass spectrometry data.

ChemInform Abstract: Domino Prins/Pinacol Reaction for the Stereoselective Synthesis of Spiro[pyran‐4,4′‐quinoline]‐2′,3′‐dione Derivatives.

A wide array of aldehydes undergo smooth cross-coupling with 3-hydroxy-3-(4-hydroxybut-1-en-2-yl)-1-methylindolin-2-one in the presence of 10 mol% BF3·OEt2 at 0 °C in dichloromethane to afford the corresponding 2,3,5,6-tetrahydro-1′H-spiro[pyran-4,4′-quinoline]-2′,3′-dione derivatives in good yields with excellent diastereoselectivity. This is the first report on the synthesis of tetrahydro-1′H-spiro[pyran-4,4′-quinoline]-2′,3′-dione scaffolds through a cascade of Prins/pinacol reactions.

Solvent‐free One‐pot Synthesis of 2,2′‐dithioxo‐[5,5′]bithiazolidinylidene‐4,4′‐diones

Solvent‐free one‐pot synthesis of 2,2′‐dithioxo‐[5,5′]bithiazolidinylidene‐4,4′‐dione (birhodanine) derivatives from the reaction of primary amines and carbon disulfide in the presence of dimethyl acetylene dicarboxylate has been reported.

Photocurrent enhancement of an efficient large band gap polymer incorporating benzodithiophene and weak electron accepting pyrrolo[3,4−c]pyrrole−1,3−dione derivatives via the insertion of a strong electron accepting thieno[3,4−b]thiophene unit

The opto-electrical, charge transport and photovoltaic properties of the highly efficient large band gap polymer, P(BDT-TDPPDT), containing electron rich 4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b']dithiophene (BDT) and a weak electron accepting 2,5-dioctyl-4,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,3(2H,5H)-dione (TDPPDT) units were modulated by the incorporation of a relatively strong electron deficient thieno[3,4-b]thiophene (TT) unit on its backbone. A new random copolymer (RP2) was prepared by polymerizing the BDT derivative with TDPPDT and TT derivatives at a 2:1:1 ratio. The estimated optical band gap (Eg) and highest occupied/lowest unoccupied molecular orbital (HOMO/LUMO) energy levels of RP2 were 1.70 eV and −5.30 eV/−3.60 eV, respectively. The determined hole mobility of RP2 was 4.0 × 10−4 cm2V −1s−1. The polymer solar cells (PSCs) prepared with a simple device configuration of ITO/PEDOT:PSS/RP2:PC70BM/Al offered a maximum power conversion efficiency (PCE) of 5.12% with an open circuit voltage (Voc) of 0.75 V, a current density (Jsc) of 12.99 mA/cm2, and a fill factor (FF) of 53%. The incorporation of a TT unit on the P(BDT-TDDPT) backbone was found to reduce the band gap by 0.41 eV and increase slightly the hole mobility of the resulting copolymer, RP2. Consequently, the PSC prepared from RP2 showed the enhanced photocurrent compared with that of the PSC prepared from P(BDT-TDPPDT).

Palladium-Catalyzed Carbonylative Annulation Reactions Using Aryl Formate as a CO Source: Synthesis of 2-Substituted Indene-1,3(2H)-dione Derivatives.

An efficient synthesis of 2-substituted indene-1,3(2H)-diones from stable and readily available 1-(2-halophenyl)-1,3-diones by employing phenyl formate as a CO source has been developed. The reaction occurred via palladium-catalyzed intramolecular carbonylative annulation using K3PO4 as a base and DMSO as a solvent at 95 °C. In this protocol, the reaction showed a broad substrate scope with good to excellent yields.

Succinimidinium hydrogensulfate ([H-Suc]HSO4) as an efficient ionic liquid catalyst for the synthesis of 5-arylidenepyrimidine-2,4,6(1H,3H,5H)-trione and pyrano-pyrimidinones derivatives

In this work, succinimidinium hydrogensulfate ([H-Suc]HSO4), a newly reported Bronsted acidic ionic liquids is used as an efficient, homogeneous and reusable catalyst for the synthesis of 5-arylidenepyrimidine-2,4,6(1H,3H,5H)-trione and pyrano[2,3-d]-pyrimidine dione derivatives. The products were formed in excellent yields over short reaction times and the catalyst can be reused several times without any appreciable loss in its activity.

Green Synthesis of Spiro[indoline‐3,4′‐pyrazolo[3,4‐b][1,6]naphthyridine]‐2,5′(1′H)‐diones Catalyzed by TsOH in Ionic Liquids

A three‐component reaction of isatin, 3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐amine, and piperidine‐2,4‐dione was treated in ionic liquids catalyzed by TsOH and provided an efficient and green method for the synthesis of spiro[indoline‐3,4′‐pyrazolo[3, 4‐b][1,6]naphthyridine]‐2,5′(1′H)‐dione derivatives in high yields.

6-Hydroxy-1,2,4-triazine-3,5(2H,4H)-dione Derivatives as Novel D-Amino Acid Oxidase Inhibitors.

A series of 2-substituted 6-hydroxy-1,2,4-triazine-3,5(2H,4H)-dione derivatives were synthesized as inhibitors of d-amino acid oxidase (DAAO). Many compounds in this series were found to be potent DAAO inhibitors, with IC50 values in the double-digit nanomolar range. The 6-hydroxy-1,2,4-triazine-3,5(2H,4H)-dione pharmacophore appears metabolically resistant to O-glucuronidation unlike other structurally related DAAO inhibitors. Among them, 6-hydroxy-2-(naphthalen-1-ylmethyl)-1,2,4-triazine-3,5(2H,4H)-dione 11h was found to be selective over a number of targets and orally available in mice. Furthermore, oral coadministration of d-serine with 11h enhanced the plasma levels of d-serine in mice compared to the oral administration of d-serine alone, demonstrating its ability to serve as a pharmacoenhancer of d-serine.

Photophysical and Computational Analysis of a Symmetrical Fluorene-Based Janus Dione Derivative

Molecular symmetry plays an important role in the physical characteristics and spectra of a molecule. However, experimental results can sometimes be counterintuitive due to unpredictable properties of a molecule. Photophysical characterization of a centrosymmetrical indacene-1,3,5,7(2H,6H)-tetraone, or Janus dione, derivative revealed a two-photon absorption maximum closely associated with the main linear absorption band (a typically two-photon forbidden transition for molecules of high symmetry). Though observed previously in similar compounds, little explanation has been offered for this anomaly. Our investigation of a symmetrical Janus dione, including linear and nonlinear photophysical characterization along with TD-DFT calculations, provides insight regarding the origin of this phenomenon.

Synthesis of Optically Pure Spiro[cyclohexane-oxindoline] Derivatives via Catalytic Asymmetric Diels-Alder Reaction of Brassard-Type Diene with Methyleneindolines.

A highly efficient N,N'-dioxide-Zn(II) complex catalytic system for the asymmetric Diels-Alder reaction of Brassard-type diene with methyleneindolines was developed. The optically pure spiro[cyclohex[3]ene-1,3'-indoline]-1'-carboxylate-2, 2'-dione derivatives containing three stereocenters were obtained in moderate yields with 98% to >99% ee in a stereospecific manner.

ChemInform Abstract: Cascade Couplings of N‐Alkyl‐N‐methacryloyl Benzamides with Ethers and Benzenesulfonohydrazides to Generate Isoquinoline‐1,3(2H,4H)‐dione Derivatives.

Two radical-mediated cascade couplings of N-alkyl-N-methacryloylbenzamides with different ethers and arylsulfonohydrazides to generate ether- and arylsulfonyl-substituted isoquinoline-1,3(2H,4H)-dione derivatives were developed. Both casccades proceeded via initially triggered functionalization of the alkene functions of the N-alkyl-N-methacryloylbenzamides, followed by ortho radical cyclizations onto the aromatic ring to give isoquinoline-1,3(2H,4H)-dione derivatives in good yields. These highly functionalized drug-like molecules will be valuable in drug discovery in the future.