30 results on '"Maria Annunziata M. Capozzi"'
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2. A comparative screening of laccase-mediator systems by white-rot fungi laccases for biocatalytic benzyl alcohol oxidation
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Ivana Marino, Eugenia Pignataro, Donatella Danzi, Francesco Cellini, Cosimo Cardellicchio, Antonino Biundo, Isabella Pisano, and Maria Annunziata M. Capozzi
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Medicine ,Science - Abstract
Abstract Production of value-added compounds from waste materials is of utmost importance for the development of a sustainable society especially regarding their use as catalysts in industrially relevant synthetic reactions. Herein, we show the production of laccases from four white-rot fungi, which were grown on agricultural residues, specifically Trametes versicolor 11269, Pleurotus ostreatus 1020, Panus tigrinus 707 and Lentinula edodes SC-495. The produced laccases were tested on a laccase-mediator system (LMS) for the biocatalytic oxidation of the model substrate benzyl alcohol into benzaldehyde. The LMS was carried out in the presence both of tetrahydrofuran as co-solvent and of the mediator 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO) due to its high redox potential and its ability to perform the oxidation. Tolerance studies showed that the dialyzed solutions were able to tolerate 1% (99:1 v/v) of co-solvent, whereas a concentration of 10% v/v had a detrimental activity. Performances in the biocatalytic oxidation of laccase solutions from different purification steps were compared. Similar conversion was observed for laccase in dialysis (raw) and gel filtration (GF) product versus commercial T. versicolor laccase. The latter oxidized almost 99% of substrate while the other laccase solutions were able to reach a conversion from 91% for the laccase solution from P. tigrinus 707 after dialysis, to 50% for the laccase solution from P. ostreatus 1020 after gel filtration. This work highlights the potential of unpurified laccase solutions to be used as catalysts in synthetic reactions. more...
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- 2022
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Catalog
3. 1-[(1S)-(4-Fluorophenyl)-((1′S)-1′-naphthalen-1-yl-ethylamino)-methyl]-naphthalen-2-trifluoromethanesulfonate
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Cosimo Cardellicchio and Maria Annunziata M. Capozzi
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Betti reaction ,aminobenzylnaphthols ,chirality ,NMR analysis ,Inorganic chemistry ,QD146-197 - Abstract
The complex structure of aminobenzylnaphthols can be easily obtained with the useful Betti reaction. These valuable compounds can give rise to chiral intermediates, that found wide application in asymmetric synthesis. 1-[(1S)-(4-Fluorophenyl)-((1′S)-1′-naphthalen-1-yl-ethylamino)-methyl]-naphthalen-2-ol 1 was treated with triflic anhydride to yield the corresponding (S,S)-triflate 2, which is a valuable intermediate in the future synthesis of aminophosphine, to be used in asymmetric catalysis. Preliminarily structural considerations based upon H(1)-NMR spectroscopy are also reported. more...
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- 2023
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4. Synthesis and Preliminary Screening of the Biological Activity of Sulindac Sulfoximine Derivatives
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Cosimo Cardellicchio, Valentino Laquintana, Rosa Maria Iacobazzi, Nunzio Denora, Antonio Scilimati, Maria Grazia Perrone, and Maria Annunziata M. Capozzi
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sulfoximines ,sulindac ,sulfoxides ,antiproliferative activity ,Technology ,Engineering (General). Civil engineering (General) ,TA1-2040 ,Biology (General) ,QH301-705.5 ,Physics ,QC1-999 ,Chemistry ,QD1-999 - Abstract
Sulindac is a well-known anti-inflammatory agent, sometimes employed as an adjuvant in antitumor therapy. Due to the recent interest in sulfoximine for its potential chemotherapeutics, we decided to transform sulindac and its methyl ester into the corresponding sulfoximines to test their antitumor activity. These compounds were fully characterized. Eventually, sulindac, sulindac methyl ester and the two novel corresponding sulfoximines were tested against malignant cells of U-87 glioblastoma, MCF-7 human breast cancer, HepG2 human liver hepatocellular carcinoma, CaCo-2 human colon cancer, and HeLa human cervical cancer. Interesting preliminary results were observed that encourage new investigations in this research theme. more...
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- 2023
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5. Correction: Capozzi, M.A.M.; Cardellicchio, C. (S,S)-2-(((Hydroxynaphth-1-yl)(4′-nitrophenyl)methyl)amino)-3-methylbutanoic Acid Methyl Ester. Molbank 2022, 2022, M1528
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Maria Annunziata M. Capozzi and Cosimo Cardellicchio
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n/a ,Inorganic chemistry ,QD146-197 - Abstract
In the original publication [...]
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- 2023
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6. (S,S)-1-(Phenyl((1′-4-nitrophenyl-ethyl)amino)methyl)-2-naphthol
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Maria Annunziata M. Capozzi and Cosimo Cardellicchio
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Betti reaction ,aminobenzylnaphthols ,chirality ,NMR analysis ,solvent free ,Inorganic chemistry ,QD146-197 - Abstract
The Betti reaction of 2-naphthol, benzaldehyde and (S)-1-(4-nitrophenyl)ethylamine without any solvent gave the corresponding aminobenzylnaphthol, that is the (S,S)-1-(phenyl((1′-4-nitrophenyl-ethyl)amino)methyl)-2-naphthol, in good yield (56%). The absolute configuration of the title compound was attributed by NMR analysis, a procedure that is reliable if compared with the data obtained by X-ray diffraction experiments. more...
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- 2022
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7. (S,S)-2-(((Hydroxynaphth-1-yl)(4′-nitrophenyl)methyl)amino)-3-methylbutanoic Acid Methyl Ester
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Maria Annunziata M. Capozzi and Cosimo Cardellicchio
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Betti reaction ,aminobenzylnaphthols ,chirality ,amino acids ,racemization ,solvent-free ,Inorganic chemistry ,QD146-197 - Abstract
The solvent-free Betti reaction of 2-naphthol, 4-nitrobenzaldehyde and (S)-valine methyl ester gave the corresponding aminobenzylnaphthol of the (S,S)-2-(((hydroxynaphth-1-yl)(4′-nitrophenyl)methyl)amino)-3-methylbutanoic acid methyl ester in good yield (59%). This product was fully characterized. We observed that the racemization that occurs in some Betti reactions with (S)-valine methyl ester was absent in this reaction, and thus the predominant (S,S)-product was obtained. more...
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- 2022
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8. Antiproliferative Activity of Aminobenzylnaphthols Deriving from the Betti Reaction
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Rosanna Mallamaci, Maria Annunziata M. Capozzi, and Cosimo Cardellicchio
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Betti reaction ,antitumor activity ,neuroblastoma ,adenocarcinoma ,Technology ,Engineering (General). Civil engineering (General) ,TA1-2040 ,Biology (General) ,QH301-705.5 ,Physics ,QC1-999 ,Chemistry ,QD1-999 - Abstract
Two aminobenzylnaphthols, which are representative items of the family of compounds synthesized with the Betti reaction, were investigated as antiproliferative agents against adenocarcinoma human colorectal (Caco-2) and human neuroblastoma (SH-SY5Y) cell lines, using cisplatin as a positive control. A better antiproliferative activity was recorded after 24 h of incubation for the first tested molecule, whereas the other one was more effective after 72 h of incubation. These results support the hypothesis that both of the tested aminobenzylnaphthols could potentially be endowed with a biological activity. more...
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- 2022
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9. Chiral Diketopyrrolo[3,4-c]pyrrole-1,2,3-1H-triazole Dyes with Highly Tuneable Properties in Solution and Thin Films
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Gianluigi Albano, Francesco Zinna, Andrea Taddeucci, Maria Annunziata M. Capozzi, Gennaro Pescitelli, Angela Punzi, Lorenzo Di Bari, and Gianluca M. Farinola
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Organic Chemistry ,Organic dyes ,General Chemistry ,Chirality ,Triazoles ,Diketopyrrolopyrroles ,Supramolecular chemistry ,Catalysis - Abstract
We have studied the impact of achiral substituents on the chiral supramolecular architectures of diketopyrrolo[3,4-c]pyrrole-1,2,3-1H-triazole (DPP) dyes. We decorated the same chiral DPP motif with substituent groups on the nitrogen atoms of the lactam moiety: the hydrophobic n-octyl alkyl chain, the hydrophilic tri(ethyleneglycol) (TEG) chain and the thermo-cleavable tert-butoxycarbonyl (t-Boc) carbamate group. In spite of having identical conjugated chromophore and chiral appendages, in aggregated form the three dyes displayed profoundly different optical,chiroptical,electrochemical and thermal features. ECD measurements revealed differences in the aggregation modes, which would be in accessible by most other techniques. We found strong chiroptical features, which would have major implications in the context of chiral organic opto-electronics and in the development of other highly innovative technological applications. more...
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- 2023
10. Sustainable protocols for direct C–H bond arylation of (hetero)arenes
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Maria Annunziata M. Capozzi, Gianluca Maria Farinola, Gianluigi Albano, and Angela Punzi
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Environmental Chemistry ,Pollution - Abstract
A comprehensive and critical overview of the sustainable strategies for direct C–H bond arylation of (hetero)arenes, based on the use of recoverable catalysts, sustainable solvents and non-conventional energy sources, has been performed. more...
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- 2022
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11. Infrared Irradiation‐Assisted Solvent‐Free Pd‐Catalyzed (Hetero)aryl‐aryl Coupling via C−H Bond Activation
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Gianfranco Decandia, Gianluca M. Farinola, Angela Punzi, Gianluigi Albano, Maria Annunziata M. Capozzi, and Nicola Zappimbulso
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Green chemistry ,Full Paper ,Chemistry ,Infrared ,General Chemical Engineering ,Aryl ,C−C coupling ,Context (language use) ,Full Papers ,solvent-free ,Combinatorial chemistry ,C−H activation ,infrared irradiation ,Coupling reaction ,Catalysis ,Organic semiconductor ,chemistry.chemical_compound ,General Energy ,synthetic methods ,Environmental Chemistry ,General Materials Science ,Energy source - Abstract
The increasing attention towards environmentally friendly synthetic protocols has boosted studies directed to the development of green and sustainable methods for direct C−H bond arylation of (hetero)arenes. In this context, here the infrared (IR) irradiation‐assisted solvent‐free Pd‐catalyzed direct C−H bond arylation of (hetero)arenes was achieved. Several heteroaryl‐aryl coupling reactions were described, also involving heterocycles commonly used as building blocks for the synthesis of organic semiconductors. The reaction tolerated many functional groups on the aromatic nuclei. The IR‐irradiation as the energy source compared favorably with thermal heating and, in combination with solvent‐free conditions, provided an important contribution to the development of protocols fitting with the principles of green chemistry., No solvent needed: Pd‐catalyzed (hetero)aryl–aryl coupling via C−H bond activation is proven in solvent‐free conditions under IR irradiation as effective and convenient energy source. The reaction efficiently works on several conjugated cores and tolerates several functional groups on aryl iodides used as coupling partners. The protocol opens the way to energy‐effective solvent‐free methods in organic synthesis. more...
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- 2021
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12. Aggregation Modes of Chiral Diketopyrrolo[3,4-c]pyrrole Dyes in Solution and Thin Films
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Gianluigi Albano, Francesco Zinna, Francesco Urraci, Maria Annunziata M. Capozzi, Gennaro Pescitelli, Angela Punzi, Lorenzo Di Bari, and Gianluca M. Farinola
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Organic Chemistry ,General Chemistry ,Catalysis - Abstract
The chiroptical features of chiral diketopyrrolo[3,4-c]pyrrole (DPP) derivatives have been only marginally investigated to date. In this regard, we have synthesized ad hoc four chiral DPP dyes, functionalized with enantiopure alkyl groups from natural sources either on the lactam moieties or on the terminal positions of the π-conjugated backbone, to promote an efficient self-assembly into chiral supramolecular structures. For each of them, the aggregation modes has been investigated by absorbance and ECD spectroscopies in conditions of solution aggregation and on thin films, considering the effects of deposition technique (drop casting vs. spin coating) and post-deposition operations (solvent and thermal annealing). The effect of the structure of lateral π-conjugated units attached to the central DPP scaffold, as well as that of the position of the alkyl chiral group, has been assessed. ECD revealed superior capability, compared to absorbance spectroscopy, to provide information on the aggregation modes and to detect the possible co-existence of multiple aggregation pathways. more...
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- 2022
13. Screening of Laccase-Mediator Systems by White-Rot Fungi Laccases for Biocatalytic Benzyl Alcohol Oxidation
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Maria Annunziata M. Capozzi, Ivana Marino, Eugenia Pignataro, Donatella Danzi, Francesco Cellini, Cosimo Cardellicchio, Antonino Biundo, and Isabella Pisano
- Abstract
Production of added value compounds from waste materials is of utmost importance for the development of a sustainable society especially regarding their use as catalysts in industrially relevant synthetic reactions. Herein, we show the production of laccases from four white-rot fungi, which were grown on agricultural residues, specifically Trametes versicolor 11269, Pleurotus ostreatus 1020, Panus tigrinus 707 and Lentinula edodes SC-495. The produced laccases were tested on biphasic laccase-mediator system (LMS) for the biocatalytic oxidation of the model substrate benzyl alcohol into benzaldehyde. The biphasic LMS was carried out in the presence both of tetrahydrofuran as co-solvent and of the mediator 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO) due to its high redox potential and its ability to perform the oxidation. Tolerance studies showed that the dialyzed solutions were able to tolerate 1% of co-solvent, while a concentration of 10% v/v negatively affected their activity. Performances in the biocatalytic oxidation of laccase solutions from different purification steps were compared. Similar conversion was observed for laccase in dialysis and gel filtration product versus commercial T. versicolor laccase. The latter oxidized almost 99% of substrate while the other laccase solutions were able to reach a conversion from 91% for the laccase solution from P. tigrinus 707 after dialysis, to 50% for the laccase solution from P. ostreatus 1020 after gel filtration. This work highlights the potential of unpurified laccase solutions to be used as catalysts in synthetic reactions. more...
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- 2022
- Full Text
- View/download PDF
14. (S,S)-2-(((Hydroxynaphth-1-yl)(4′-nitrophenyl)methyl)amino)-3-methylbutanoic Acid Methyl Ester
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Cosimo Cardellicchio and Maria Annunziata M. Capozzi
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Organic Chemistry ,Physical and Theoretical Chemistry ,Biochemistry - Abstract
The solvent-free Betti reaction of 2-naphthol, 4-nitrobenzaldehyde and (S)-valine methyl ester gave the corresponding aminobenzylnaphthol of the (S,S)-2-(((hydroxynaphth-1-yl)(4′-nitrophenyl)methyl)amino)-3-methylbutanoic acid methyl ester in good yield (59%). This product was fully characterized. We observed that the racemization that occurs in some Betti reactions with (S)-valine methyl ester was absent in this reaction, and thus the predominant (S,S)-product was obtained. more...
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- 2022
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15. (S,S)-1-(Phenyl((1′-4-nitrophenyl-ethyl)amino)methyl)-2-naphthol
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Cosimo Cardellicchio and Maria Annunziata M. Capozzi
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Organic Chemistry ,Physical and Theoretical Chemistry ,Biochemistry - Abstract
The Betti reaction of 2-naphthol, benzaldehyde and (S)-1-(4-nitrophenyl)ethylamine without any solvent gave the corresponding aminobenzylnaphthol, that is the (S,S)-1-(phenyl((1′-4-nitrophenyl-ethyl)amino)methyl)-2-naphthol, in good yield (56%). The absolute configuration of the title compound was attributed by NMR analysis, a procedure that is reliable if compared with the data obtained by X-ray diffraction experiments. more...
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- 2022
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16. New insights into the titanium-mediated enantioselective oxidation of fluorinated aryl benzyl sulfides and aryl phenacyl sulfides
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Maria Annunziata M. Capozzi, Cosimo Cardellicchio, Gennaro Pescitelli, and Vanni Frascaro
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Sulfide ,chemistry.chemical_element ,Circular dichroism ,010402 general chemistry ,Phenacyl ,01 natural sciences ,Biochemistry ,Catalysis ,chemistry.chemical_compound ,Drug Discovery ,chemistry.chemical_classification ,010405 organic chemistry ,Chemistry ,Aryl ,Organic Chemistry ,Enantioselective synthesis ,Sulfoxide ,Combinatorial chemistry ,Hydrobenzoin ,0104 chemical sciences ,Cumene hydroperoxide ,Oxidation mechanism ,Titanium - Abstract
A fruitful switch from tert-butyl to cumene hydroperoxide was able to overcome a difficulty arose in the enantioselective oxidation of fluorinated aryl benzyl sulfide with hydroperoxides in the presence of a titanium/(S, S)-hydrobenzoin catalyst. New experiments show the complementarity of the old and the new protocols and indicate unequivocally the right choice leading to the corresponding highly enantioenriched sulfoxides. Moreover, in a totally unexpected way, the new protocol was able to overcome another difficulty arose in another field of research, that is the enantioselective oxidation of a fluorinated aryl phenacyl sulfide. Also in this case, the complementarity of behavior is acting. Finally, this investigation gives new support to the attribution of configuration of sulfoxides with ECD techniques, but only if the protocol outlined in our past research was followed thoroughly. more...
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- 2019
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17. Stacked aryl groups in P-resolved cyclic phosphonamides as a new conformational constraint
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Claudia Pigliacelli, Maria Annunziata M. Capozzi, Giancarlo Terraneo, and Cosimo Cardellicchio
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Aryl ,Synthon ,Supramolecular chemistry ,Stacking ,Aromaticity ,02 engineering and technology ,General Chemistry ,Nuclear magnetic resonance spectroscopy ,010402 general chemistry ,021001 nanoscience & nanotechnology ,Condensed Matter Physics ,Crystal engineering ,01 natural sciences ,0104 chemical sciences ,chemistry.chemical_compound ,Crystallography ,aryl-stacked structures ,chemistry ,chiral cyclic phosphonamides ,weak interactions ,General Materials Science ,Conformational constraints ,0210 nano-technology ,Chirality (chemistry) - Abstract
Along the lines of a systematic investigation of conformational constraints promoted by weak interactions, the aryl-stacked structures of some chiral cyclic phosphonamides synthesised with the aid of Betti bases as chirality inducers were investigated by X-ray diffraction analysis and NMR spectroscopy. The synthesised systems showed the stacked conformation between two of their aryl groups, leading to pre-organized structures. The pi-pi stacking motif between the aromatic rings was observed in solid state and in solution, suggesting that this supramolecular synthon could be used as a conformational constraining tool in the development of drug molecule candidates based on chiral cyclic phosphonamides. The disabling of the pi-pi stacking motif was pursued by adding an ortho-substituent on one aromatic ring. more...
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- 2019
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18. Supramolecular synthons in fluorinated benzyl nitrophenyl sulfides
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Cosimo Cardellicchio, Joan F. Piniella, Maria Annunziata M. Capozzi, and Angel Alvarez-Larena
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chemistry.chemical_classification ,Sulfide ,sulfides ,Aryl ,Synthon ,Supramolecular chemistry ,chemistry.chemical_element ,02 engineering and technology ,General Chemistry ,010402 general chemistry ,021001 nanoscience & nanotechnology ,01 natural sciences ,Catalysis ,0104 chemical sciences ,Crystal ,Crystallography ,chemistry.chemical_compound ,chemistry ,fluorine ,assembly interactions ,Materials Chemistry ,Fluorine ,Moiety ,0210 nano-technology ,Single crystal - Abstract
Two crystalline benzyl phenyl sulfides, bearing at the same time both a pentafluorophenyl and a nitrophenyl moiety in two different assemblies, were investigated by means of single crystal X-ray diffraction. The main assembly interactions were recognized and compared with the different behaviors of analogous sulfides bearing only one of these two functional groups. Since short contacts involving fluorine atoms have been a source of controversy, their contribution to the stability of the crystal was analyzed both with the help of Hirshfeld surface analysis, and with a comparison with items in the Cambridge Structural Database. The situation of a gauche-conformed sulfide having two contemporary interactions involving electron poor aryl groups is of particular interest. more...
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- 2019
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19. 1,5-Diaminonaphtalene is a Highly Performing Electron-Transfer Secondary-Reaction Matrix for Laser Desorption Ionization Mass Spectrometry of Indolenine-Based Croconaines
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Maria Annunziata M. Capozzi, Angela Punzi, Cosima Damiana Calvano, Tommaso R. I. Cataldi, Gianluca M. Farinola, and Francesco Palmisano
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010405 organic chemistry ,Chemistry ,General Chemical Engineering ,Croconic acid ,Protonation ,General Chemistry ,010402 general chemistry ,Mass spectrometry ,Photochemistry ,01 natural sciences ,Article ,0104 chemical sciences ,Adduct ,chemistry.chemical_compound ,Fragmentation (mass spectrometry) ,Ionization ,Molecule ,Malononitrile - Abstract
Croconaine dyes are appealing molecules synthesized via the condensation of croconic acid and reactive electron-donating aromatic or heterocyclic systems. Here, matrix-assisted laser desorption/ionization (MALDI) mass spectrometry (MS) investigation of indolenine-based croconaines is presented for the first time. Archetype proton-transfer matrices, such as 2,5-dihydroxybenzoic acid (DHB) and α-cyano-4-hydroxycinnamic acid (CHCA), 9-aminoacridine (9AA) as the protonating/deprotonating matrix, and electron-transfer (ET) secondary-reaction matrices, such as 1,5-diaminonapthalene (DAN) and trans-2-[3-(4-t-butyl-phenyl)-2-methyl-2-propenylidene]malononitrile (DCTB), were investigated. DHB, CHCA, and 9AA generate a mix of odd-electron molecular ions and protonated, sodiated, and potassiated adducts. Among the ET matrices, DAN was found to be capable of directing the ionization process toward the exclusive formation of odd-electron molecular ions M+• without fragmentation. MALDI tandem MS provides useful structural characterization of croconaine dyes, thus making identification very straightforward for all investigated compounds. Interestingly the fragmentation of bromo-containing croconaines revealed, for the first time, the gas-phase formation of a bromime cation [Br]+. more...
- Published
- 2018
20. Stereoselection in the Betti reaction of valine methyl esters
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Cosimo Cardellicchio and Maria Annunziata M. Capozzi
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010405 organic chemistry ,Chemistry ,Betti reaction ,Organic Chemistry ,010402 general chemistry ,Ring (chemistry) ,01 natural sciences ,Chemical reaction ,Catalysis ,0104 chemical sciences ,Stereocenter ,Inorganic Chemistry ,Benzaldehyde ,chemistry.chemical_compound ,Yield (chemistry) ,Organic chemistry ,Amine gas treating ,Physical and Theoretical Chemistry ,Chirality (chemistry) - Abstract
The multi-component Betti reaction of 2-naphthol, benzaldehyde and (S)-amines, that usually provides highly valuable aminobenzylnaphthol bearing two stereogenic centers, yielded a completely racemic product, when (S)-valine methyl ester was employed as the amine in the usual reaction protocol. The cause of this drawback, that appears to be overlooked in the literature, was investigated. As a result, new reaction conditions were set up, that were able to yield the expected useful product, having two fully resolved stereogenic centers. Furthermore, when the effect of substituents on the phenyl ring was preliminarily studied, we found that 4-fluoro- and 4-chlorobenzaldeyde gave stereoisomerically pure compounds also in the original reaction protocol. more...
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- 2017
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21. Pd-Catalyzed Thiophene–Aryl Coupling Reaction via C–H Bond Activation in Deep Eutectic Solvents
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Alessandra Operamolla, Donato Ivan Coppi, Francesco Babudri, Sergio Matera, Maria Annunziata M. Capozzi, Gianluca M. Farinola, Roberta Ragni, and Angela Punzi
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010405 organic chemistry ,Aryl ,Organic Chemistry ,Inorganic chemistry ,chemistry.chemical_element ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Coupling reaction ,0104 chemical sciences ,Catalysis ,Deep eutectic solvent ,chemistry.chemical_compound ,chemistry ,Polymer chemistry ,Thiophene ,Physical and Theoretical Chemistry ,Eutectic system ,Choline chloride ,Palladium - Abstract
Direct arylation of 5-octylthieno[3,4-c]pyrrole-4,6-dione with a series of functionalized aryl iodides via C-H bond activation is demonstrated in a deep eutectic solvent made of choline chloride and urea in non-anhydrous conditions and without exclusion of air. This is the first demonstration of a thiophene-aryl coupling via direct arylation in deep eutectic solvents. more...
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- 2017
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22. A Convenient, Mild, and Green Synthesis of NH-Sulfoximines in Flow Reactors
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Michael Andresini, Cosimo Cardellicchio, Renzo Luisi, Sonia De Angelis, Giuseppe Romanazzi, Leonardo Degennaro, Arianna Tota, and Maria Annunziata M. Capozzi
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Aqueous solution ,010405 organic chemistry ,Continuous flow ,Chemistry ,Continuous reactor ,Organic Chemistry ,Flow chemistry ,010402 general chemistry ,01 natural sciences ,0104 chemical sciences ,Batch processing ,Organic chemistry ,Physical and Theoretical Chemistry ,Microreactor ,Flow process - Abstract
NH-sulfoximines are emerging as useful and important targets in drug discovery and synthetic organic chemistry. We report herein the development of an efficient, convenient, and sustainable continuous-flow strategy, for the direct, straightforward preparation of NH-sulfoximines by using sulfides or sulfoxides as suitable starting material. The flow process uses PhI(OAc)2 as the oxidant and aqueous solutions of ammonia as the N source. The scope of the reaction has been demonstrated by using several substituted sulfides and sulfoxides including enantioenriched and biologically relevant starting materials. The flow strategy was found to be more convenient with respect to conventional batch processing. more...
- Published
- 2017
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23. Structural insights into methyl- or methoxy-substituted 1-(a-aminobenzyl)-2-naphthol structures: the role of C--H p interactions
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Giancarlo Terraneo, Maria Annunziata M. Capozzi, and Cosimo Cardellicchio
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crystal structure ,Crystal structure ,010402 general chemistry ,01 natural sciences ,Medicinal chemistry ,Inorganic Chemistry ,Crystal ,chemistry.chemical_compound ,Group (periodic table) ,Materials Chemistry ,Moiety ,Physical and Theoretical Chemistry ,CrystalExplorer ,010405 organic chemistry ,Hydrogen bond ,aminobenzylnaphthol ,Condensed Matter Physics ,Small molecule ,0104 chemical sciences ,Hirshfeld ,small molecules ,Crystal explorer ,chemistry ,C—H⋅⋅⋅π interactions ,packing ,CH···pi interactions ,2-Naphthol ,Methyl group ,Aminobenzylnaphthol ,Packing - Abstract
Aminobenzylnaphthols are a class of compounds containing a large aromatic molecular surface which makes them suitable candidates to study the role of C—H...π interactions. We have investigated the effect of methyl or methoxy substituents on the assembling of aromatic units by preparing and determining the crystal structures of (S,S)-1-{(4-methylphenyl)[(1-phenylethyl)amino]methyl}naphthalen-2-ol, C26H25NO, and (S,S)-1-{(4-methoxyphenyl)[(1-phenylethyl)amino]methyl}naphthalen-2-ol, C26H25NO2. The methyl group influenced the overall crystal packing even if the H atoms of the methyl group did not participate directly either in hydrogen bonding or C—H...π interactions. The introduction of the methoxy moiety caused the formation of new hydrogen bonds, in which the O atom of the methoxy group was directly involved. Moreover, the methoxy group promoted the formation of an interesting C—H...π interaction which altered the orientation of an aromatic unit. more...
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- 2019
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24. Solvent-Free Pd-Catalyzed Heteroaryl-Aryl Coupling via C-H Bond Activation for the Synthesis of Extended Heteroaromatic Conjugated Molecules
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Angela Punzi, Simone Di Noja, Nicola Zappimbulso, Gianluca M. Farinola, Roberta Ragni, and Maria Annunziata M. Capozzi
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Solvent free ,C h bond ,010405 organic chemistry ,Chemistry ,Aryl ,Organic Chemistry ,Conjugated system ,010402 general chemistry ,01 natural sciences ,Combinatorial chemistry ,0104 chemical sciences ,Catalysis ,Coupling (electronics) ,chemistry.chemical_compound ,Molecule - Abstract
Direct arylation of thienopyrrolodione, diketopyrrolopyrroles, benzodithiophene derivatives, and fluorinated heteroarenes with functionalized aryl iodides is proven in solvent-free and non-anhydrous conditions. The reaction is performed in the presence of air and tolerates several functional groups on both the coupling partners, enabling a convenient synthesis of extended heteroaromatic conjugated molecules. more...
- Published
- 2018
25. Croconaines as molecular materials for organic electronics: synthesis, solid state structure and use in transistor devices
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Ernesto Mesto, Emanuela Schingaro, Gianluca M. Farinola, Paolo Samorì, Vincenzo Fino, Sara Bonacchi, Tim Leydecker, Emanuele Orgiu, Maria Annunziata M. Capozzi, Claudia Carlucci, Roberta Musio, M. Suriano, Angela Punzi, univOAK, Archive ouverte, Università degli studi di Bari Aldo Moro = University of Bari Aldo Moro (UNIBA), Institut de Science et d'ingénierie supramoléculaires (ISIS), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique, and Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS) more...
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Materials science ,Solid-state ,Nanotechnology ,010402 general chemistry ,DFT ,01 natural sciences ,Solid state structure ,law.invention ,ENERGY ,law ,BINDING ,ABSORPTION ,Materials Chemistry ,Molecule ,Molecular materials ,Organic electronics ,[CHIM.MATE] Chemical Sciences/Material chemistry ,DERIVATIVES ,010405 organic chemistry ,Ambipolar diffusion ,Transistor ,NIR ,[CHIM.MATE]Chemical Sciences/Material chemistry ,General Chemistry ,[SPI.TRON] Engineering Sciences [physics]/Electronics ,[SPI.TRON]Engineering Sciences [physics]/Electronics ,0104 chemical sciences ,INFRARED CROCONIUM DYE - Abstract
International audience; A series of indolenine-based croconaines has been synthesized and their molecular structure has been investigated together with their solid state organization. Ambipolar semiconducting properties have been demonstrated in thin-film transistors, suggesting croconaines as a new class of molecular materials for organic electronics. more...
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- 2016
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26. Circular Dichroism and TDDFT Investigation of Chiral Fluorinated Aryl Benzyl Sulfoxides
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Lorenzo Di Bari, Maria Annunziata M. Capozzi, Roberto Berardozzi, Ciro A. Guido, Cosimo Cardellicchio, and Gennaro Pescitelli
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Circular dichroism ,education.field_of_study ,Aryl ,Organic Chemistry ,Population ,Absolute configuration ,Sulfoxide ,Aromaticity ,Time-dependent density functional theory ,Photochemistry ,chemistry.chemical_compound ,chemistry ,Computational chemistry ,Molecular orbital ,Physical and Theoretical Chemistry ,education - Abstract
A series of ten chiral aryl benzyl sulfoxides with perfluorinated aryl or benzyl rings, obtained by enantioselective oxidation of sulfides, has been investigated by means of electronic circular dichroism (ECD) spectroscopy and time-dependent DFT (TDDFT) calculations. The (per)fluorination of the aromatic rings has a large impact on the conformer population, the molecular orbitals shape, and the character of electronic transitions. In this series, the transition responsible for the “sulfoxide primary” CD band has a large charge transfer (CT) character, as demonstrated by the CT metric index ΓNTO. As a consequence, global DFT hybrids such as B3LYP are largely inaccurate in the prediction of excited states; nevertheless, a correct simulation of CD spectra may be achieved by using range-separated functionals such as CAM-B3LYP. The use of the empirical Mislow's rule for assigning the absolute configuration is strongly discouraged for this class of compounds. more...
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- 2015
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27. Stereochemical analysis of beta-keto sulfoxides by circular dichroism
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Lorenzo Di Bari, Gennaro Pescitelli, Cosimo Cardellicchio, Marcin Górecki, Maria Annunziata M. Capozzi, and Gianluigi Albano
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Circular dichroism ,Stereochemistry ,conformational search ,Solid-state ,solid-state ECD/TDDFT ,solvent effects ,010402 general chemistry ,01 natural sciences ,Catalysis ,Analytical Chemistry ,Computational chemistry ,Drug Discovery ,Spectroscopy ,Quantum chemical ,Pharmacology ,010405 organic chemistry ,Chemistry ,chiroptical spectroscopy ,density functional calculations ,Drug Discovery3003 Pharmaceutical Science ,Organic Chemistry ,Absolute configuration ,0104 chemical sciences ,Enantiopure drug ,Standard protocol ,Solvent effects - Abstract
Three beta-keto sulfoxides (1-3) were synthesized in enantiopure form and investigated by means of circular dichroism (CD) spectroscopy, both in electronic and vibrational range (ECD, VCD), in combination with quantum chemical calculations. For compound 2, the X-ray structure was available; thus, the ECD in the solid state was also considered to reveal the differences between the molecular species in both states. Despite the simplicity of all ?-keto sulfoxides under investigation (29 atoms), reproducing even the major spectral VCD features failed for two compounds, making the use of VCD not ideal to assign their absolute configuration in a reliable way. We demonstrated, however, that the use of ECD spectroscopy, both in solution and solid state, can easily, unambiguously, and without any complication simulate all bands by applying the standard protocol for calculations. This study may stimulate the debate on the need of the use of two chiroptical methods simultaneously in the determination of absolute configurations. more...
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- 2018
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28. A dichotomy in the enantioselective oxidation of aryl benzyl sulfides: A combined experimental and computational work
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Maria Annunziata M. Capozzi, Cosimo Cardellicchio, Matteo Calvaresi, Andrea Bottoni, Capozzi, Maria Annunziata M., Bottoni, Andrea, Calvaresi, Matteo, and Cardellicchio, Cosimo
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DFT computations ,enantioselective oxidation ,aryl benzyl sulfide ,010402 general chemistry ,01 natural sciences ,Biochemistry ,DFT ,chemistry.chemical_compound ,Drug Discovery ,Moiety ,Phenyl group ,Reactivity (chemistry) ,Titanium ,010405 organic chemistry ,Aryl ,Organic Chemistry ,Enantioselective synthesis ,Sulfoxide ,Combinatorial chemistry ,Hydrobenzoin ,0104 chemical sciences ,Enantiopure drug ,chemistry ,Cumene hydroperoxide ,Oxidation mechanism - Abstract
Pentafluorobenzyl pentafluorophenyl sulfide is oxidised with moderate e.e. value and a low yield by the usually highly successful oxidation protocol based upon tert-butyl hydroperoxide (TBHP) in the presence of a titanium/hydrobenzoin complex. This disappointing result resisted until the present work, in which the switch of the oxidation agent (from TBHP to cumene hydroperoxide), suggested by our previous computations, yielded the enantiopure sulfoxide. This valuable chiral compound was obtained in good yields (76%) without resorting to a chromatographic separation. DFT computations uncovered that this favourable reactivity was originated by a stabilizing π−π−stacking between the phenyl group of the oxidant and the pentafluorophenyl moiety of the substrate. more...
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- 2018
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29. ChemInform Abstract: The Search for Exceptions in the Highly Enantioselective Titanium Catalyzed Oxidation of Aryl Benzyl Sulfides
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Gabriella Cavallo, Maria Annunziata M. Capozzi, Giancarlo Terraneo, and Cosimo Cardellicchio
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chemistry.chemical_compound ,Chemistry ,Aryl ,Enantioselective synthesis ,chemistry.chemical_element ,Organic chemistry ,Stereoselectivity ,General Medicine ,Titanium ,Catalysis - Abstract
The title reaction generally proceeds with high yields and provides the products with high stereoselectivity.
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- 2015
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30. The search for exceptions in the highly enantioselective titanium catalysed oxidation of aryl benzyl sulfides
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Gabriella Cavallo, Giancarlo Terraneo, Cosimo Cardellicchio, and Maria Annunziata M. Capozzi
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Titanium ,CD spectra ,Chemistry ,Aryl ,Drug Discovery3003 Pharmaceutical Science ,Organic Chemistry ,Enantioselective synthesis ,chemistry.chemical_element ,Sulfoxide ,Medicinal chemistry ,Redox ,Biochemistry ,Hydrobenzoin ,X-ray diffraction ,chemistry.chemical_compound ,Drug Discovery ,Stereoselectivity ,Titanium isopropoxide - Abstract
After the discovery of a few cases of lower enantioselectivity in the oxidation of aryl benzyl sulfides with hydroperoxides in the presence of a complex between titanium isopropoxide and (S, S)-hydrobenzoin, a screening of the oxidation of new substrates that are related to the structures that gave low ee values, was performed. From this screening, we confirmed that only a few sulfides remain as exceptions within a framework of exceptionally high stereoselectivity of the oxidation reaction. Moreover, the exceptions are clearly identified and are connected to particular coordinating moieties present on the aryl groups. (C) 2015 Elsevier Ltd. All rights reserved more...
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- 2015
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