scholarly journals 5-Phenyl-10,15,20-Tris(4-sulfonatophenyl)porphyrin: Synthesis, Catalysis, and Structural Studies

Molecules ◽  
2018 ◽  
Vol 23 (12) ◽  
pp. 3363 ◽  
Author(s):  
Aitor Arlegui ◽  
Zoubir El-Hachemi ◽  
Joaquim Crusats ◽  
Albert Moyano
Keyword(s):  
Alder Reaction ◽  
Water Soluble ◽  
Experimental Conditions ◽  
One Pot ◽  
Force Microscopy ◽  
Diels Alder Reaction ◽  
Transmission Electron ◽  
Porphyrin Synthesis ◽  
The One ◽  
Water Soluble Porphyrin

A convenient protocol for the preparation of 5-phenyl-10,15,20-tris(4-sulfonatophenyl)porphyrin, a water-soluble porphyrin with unique aggregation properties, is described. The procedure relies on the one-pot reductive deamination of 5-(4-aminophenyl)-10,15,20-tris(4-sulfonatophenyl)porphyrin, that can be in turn easily obtained from 5,10,15,20-tetraphenylporphyrin by a known three-step sequence involving mononitration, nitro to amine reduction and sulfonation of the phenyl groups. This method provides the title porphyrin in gram scale, and compares very favorably with the up to now only described procedure based on the partial sulfonation of TPP, that involves a long and tedious chromatographic enrichment of the final compound. This has allowed us to study for the first time both the use of its zwitterionic aggregate as a supramolecular catalyst of the aqueous Diels–Alder reaction, and the morphology of the aggregates obtained under optimized experimental conditions by atomic force microscopy and also by transmission electron cryomicroscopy.

Synthesis and X-ray powder diffraction data of cis-4-(4-methoxyphenyl)-3-methyl-6-nitro-2-phenyl-1,2,3,4-tetrahydroquinoline

2013 ◽  
Vol 28 (4) ◽  
pp. 307-311 ◽  
Author(s):  
M.A. Macías ◽  
J.A. Henao ◽  
Arnold R. Romero Bohórquez ◽  
Vladimir V. Kouznetsov
Keyword(s):  
Powder Diffraction ◽  
Alder Reaction ◽  
Diels Alder ◽  
Gas Chromatography Mass Spectrometry ◽  
One Pot ◽  
X Ray ◽  
Cell Parameters ◽  
Diels Alder Reaction ◽  
The One ◽  
C Nmr

The 2,4-diaryl 1,2,3,4-tetrahydroquinoline derivative (1), described in the title (Chemical formula: C23H22N2O3), was synthesized via the “one-pot” three-component imino Diels–Alder reaction catalyzed by Cu(OTf)2. Molecular characterization was performed by 1H and 13C NMR, Fourier transform-infrared, and gas chromatography-mass spectrometry. The X-ray powder diffraction pattern for the title compound was analyzed and found to be crystallized in an orthorhombic system with space group P212121 (No. 19) and refined unit-cell parameters a = 8.6415(8) Å, b = 12.679(2) Å, c = 17.601(2) Å, and V = 1928.4(2) Å3.

Synthesis of gold nanocubes in aqueous solution with remarkable shape-selectivity

2011 ◽  
Vol 15 (05n06) ◽  
pp. 441-448 ◽  
Author(s):  
Adelaide Miranda ◽  
Eliana Malheiro ◽  
Peter Eaton ◽  
Patrícia A. Carvalho ◽  
Baltazar de Castro ◽  
...  
Keyword(s):  
Electron Microscopy ◽  
Shape Selectivity ◽  
Water Soluble ◽  
Force Microscopy ◽  
Atomic Force ◽  
Transmission Electron ◽  
Gold Precursor ◽  
Average Size ◽  
Water Soluble Porphyrin ◽  
Selection Of

This paper reports a facile method to prepare gold nanocubes with an average size length of 13 ± 2 nm, a shape selectivity >90%, and a very good reproducibility. The gold nanocubes were prepared by photocatalytic reduction of Au(III) using a cationic, water soluble porphyrin as the photocatalyst, and cetyltrimethylammonium bromide as the capping agent. The synthesis is performed in water, at pH 7, and room temperature. The nanocubes were characterized by transmission electron microscopy, scanning electron microscopy, atomic force microscopy, and X-ray phototelectron spectroscopy. Shape selectivity for the synthesis of nanocubes is due to a different rate of growth of the (100) and (111) facets of the nanoparticles, and such control in this synthesis is achieved by careful selection of the initial gold precursor for the photocatalytic cycle.

Proline triflate catalysed Diels–Alder reaction in the synthesis of tetrahydroquinoline derivatives

2009 ◽  
Vol 2009 (8) ◽  
pp. 499-504 ◽  
Author(s):  
Jianjun Li ◽  
Jia Li ◽  
Weike Su
Keyword(s):  
Aromatic Amines ◽  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
One Pot Synthesis ◽  
Diels Alder Reaction ◽  
The One ◽  
High Stereoselectivity

Proline triflate was found to catalyse efficiently the one-pot synthesis of 2H-pyranotetrahydroquinolines from aryl imines, and 3,4-dihydro-2 H-pyran with high stereoselectivity. The aryl imines were formed in situ from aromatic amines and arylaldehydes.

scholarly journals Efficient synthesis of polyfunctionalized carbazoles and pyrrolo[3,4-c]carbazoles via domino Diels–Alder reaction

2021 ◽  
Vol 17 ◽  
pp. 2425-2432
Author(s):  
Ren-Jie Fang ◽  
Chen Yan ◽  
Jing Sun ◽  
Ying Han ◽  
Chao-Guo Yan
Keyword(s):  
Room Temperature ◽  
Alder Reaction ◽  
Diels Alder ◽  
Efficient Synthesis ◽  
One Pot ◽  
Diels Alder Reaction ◽  
Acid Catalyzed ◽  
The One ◽  
High Yields ◽  
Ddq Oxidation

The p-TsOH-catalyzed Diels–Alder reaction of 3-(indol-3-yl)maleimides with chalcone in toluene at 60 °C afforded two diastereoisomers of tetrahydropyrrolo[3,4-c]carbazoles, which can be dehydrogenated by DDQ oxidation in acetonitrile at room temperature to give the aromatized pyrrolo[3,4-c]carbazoles in high yields. On the other hand, the one-pot reaction of 3-(indol-3-yl)-1,3-diphenylpropan-1-ones with chalcones or benzylideneacetone in acetonitrile in the presence of p-TsOH and DDQ resulted in polyfunctionalized carbazoles in satisfactory yields. The reaction mechanism included the DDQ oxidative dehydrogenation of 3-(indol-3-yl)-1,3-diphenylpropan-1-ones to the corresponding 3-vinylindoles, their acid-catalyzed Diels–Alder reaction and sequential aromatization process.

scholarly journals Efficient synthesis of polyfunctionalized carbazoles and pyrrolo[3,4-c]carbazoles via domino Diels-Alder reaction

2021 ◽  
Author(s):  
Ren-Jie Fang ◽  
Chen Yan ◽  
Jing Sun ◽  
Ying Han ◽  
Chao-Guo Yan
Keyword(s):  
Room Temperature ◽  
Alder Reaction ◽  
Diels Alder ◽  
Efficient Synthesis ◽  
One Pot ◽  
Diels Alder Reaction ◽  
Acid Catalyzed ◽  
The One ◽  
High Yields ◽  
Ddq Oxidation

p-TsOH catalyzed Diels-Alder reaction of 3-(indol-3-yl)maleimides with chalcone in toluene at 60 oC afforded two diastereoisomers of tetrahydropyrrolo[3,4-c]carbazoles, which can be dehydrogenated by DDQ oxidation in acetonitrile at room temperature to give the aromatized pyrrolo[3,4-c]carbazoles in high yields. On the other hand, the one-pot reaction of 3-(indol-3-yl)-1,3-diphenylpropan-1-ones with chalcones in acetonitrile in the presence of p-TsOH and DDQ resulted in polyfunctionalized carbazoles in satisfactory yields. The reaction mechanism included DDQ oxidative dehydrogenation of 3-(indol-3-yl)-1,3-diphenylpropan-1-ones to the corresponding 3-vinylindoles, its acid-catalyzed Diels-Alder reaction and sequential aromatization process.

scholarly journals Preparación simple de nuevas N-(6-metil-2-nitrofenil-1,2,3,4-tetrahidroquinolin-4-il) pirrolidin-2-onas y su análisis espectroscópico. Objetivos.

2011 ◽  
Vol 16 (2) ◽  
pp. 160 ◽  
Author(s):  
John H. Bermudez ◽  
José Luis Pinto ◽  
Carlos Mario Meléndez ◽  
José A. Henao ◽  
Vladimir V. Kouznetsov
Keyword(s):  
Cycloaddition Reaction ◽  
2D Nmr ◽  
Alder Reaction ◽  
Diels Alder ◽  
Nmr Studies ◽  
One Pot ◽  
Isolation And Purification ◽  
One Pot Synthesis ◽  
Diels Alder Reaction ◽  
The One

<p><strong>Objectives. </strong>To prepare new N-(1,2,3,4-tetrahydroquinolin-4-yl) pyrrolidin-2-one molecules and to characterize them by spectroscopic methods. <strong>Materials and methods. </strong>All reagents were purchased from Aldrich, commercial grade. The purity of the products and the composition of the reaction mixtures were monitored by thin layer chromatography over Silufol UV<sub>254</sub> chromatoplates (0.25 mm). Product isolation and purification were performed by column chromatography (SiO<sub>2</sub>), using ethyl acetate. <strong>Results.</strong> Preparation of new N-(2-nitrophenyl-1,2,3,4-tetrahydroquinolin-4-yl) pyrrolidin-2-ones has been achieved via the one-pot synthesis, based on a BiCl<sub>3</sub>-catalyzed imino Diels-Alder cycloaddition reaction of toluidine, N-vinylpyrrolidin-2-one and 4-nitro- or 3-nitrobenzaldehydes. The structure of the pyrrolidine derivatives was confirmed by <sup>1</sup>H nmr and <sup>13</sup>C nmr studies, in addition to inverse-detected 2D NMR experiments and monocrystal X-ray diffraction. <strong>Conclusions. </strong>An efficient, economic, and fast synthetic route (multi-component imino Diels-Alder reaction) was employed in the construction of several new tetrahydroquinoline derivatives, useful and attractive rigid skeleton with well-defined stereochemistry.</p> <p> </p> <p><strong>Key words: </strong>tetrahydroquinoline derivatives, N-substituted pyrrolidin-2-ones, three component imino Diels-Alder reaction, one-pot synthesis.</p>

scholarly journals One-pot cross-enyne metathesis (CEYM)–Diels–Alder reaction of gem-difluoropropargylic alkynes

2013 ◽  
Vol 9 ◽  
pp. 2688-2695 ◽  
Author(s):  
Santos Fustero ◽  
Paula Bello ◽  
Javier Miró ◽  
María Sánchez-Roselló ◽  
Günter Haufe ◽  
...  
Keyword(s):  
Research Group ◽  
Alder Reaction ◽  
Diels Alder ◽  
Internal Source ◽  
Enyne Metathesis ◽  
One Pot ◽  
Diels Alder Reaction ◽  
Heterocyclic Derivatives ◽  
The One

Propargylic difluorides 1 were used as starting substrates in a combination of cross-enyne metathesis and Diels–Alder reactions. Thus, the reaction of 1 with ethylene in the presence of 2nd generation Hoveyda–Grubbs catalyst generates a diene moiety which in situ reacts with a wide variety of dienophiles giving rise to a small family of new fluorinated carbo- and heterocyclic derivatives in moderate to good yields. This is a complementary protocol to the one previously described by our research group, which involved the use of 1,7-octadiene as an internal source of ethylene.

Aza-Diels-Alder Reaction Between 1,2-Diaza-1,3-dienes and β-Aryl-α,β-unsaturated Carbonyl Compounds. Easy One-pot Entry to 2’-Oxo-imidazo[1’,5’- f]tetrahydropyridazine

2014 ◽  
Vol 10 (6) ◽  
pp. 951-960
Author(s):  
Orazio Attanasi ◽  
Luca Bianchi ◽  
Maurizio D’Auria ◽  
Gianfranco Favi ◽  
Fabio Mantellini ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
Diels Alder Reaction

scholarly journals A Water-Soluble Copper-Immobilized Covalent Organic Framework Functioning as an “OFF–ON” Fluorescent Sensor for Amino Acids

2021 ◽  
Author(s):  
Lamiaa Reda Ahmed ◽  
Ahmed F. M. EL-Mahdy ◽  
Cheng-Tang Pan ◽  
Shiao-Wei Kuo
Keyword(s):  
Amino Acids ◽  
Fluorescent Sensor ◽  
Water Soluble ◽  
One Pot ◽  
Covalent Organic Framework ◽  
The One ◽  
Organic Framework

In this paper, we describe the construction of a new fluorescent hydroxyl- and hydrazone-based covalent organic framework (TFPB-DHTH COF) through the one-pot polycondensation of 1,3,5-tris(4-formylphenyl)benzene (TFPB) and 2,5-dihydroxyterephthalohydrazide (DHTH) under...

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