Optimization of the Suzuki coupling reaction in the synthesis of 2‐[(2‐substituted)phenyl]pyrrole derivatives

Alešković, Marija; Basarić, Nikola; Mlinarić‐Majerski, Kata

doi:10.1002/jhet.792

Cited by 16 publications

(9 citation statements)

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“…2‐(4‐Aminophenyl)pyrrole ( 2 b ) was obtained from 4‐aminoacetophenone oxime and 1,2‐dichloroethane . 2‐(2‐Aminophenyl)pyrrole was prepared (in ≈40 % yield) by a three‐stage reaction, involving Suzuki cross‐coupling of N‐tert ‐butoxycarbonyl‐2‐pyrroleboronic acid with ortho ‐nitrobromo‐ or ‐iodobenzene, abstraction of tert ‐butoxycarbonyl moiety in 2‐(2‐nitrophenyl)pyrrole and reduction of the nitro group to the amine fragment …”

Section: Resultsmentioning

confidence: 99%

Environment‐Responsive 8‐CF₃‐BODIPY Dyes with Aniline Groups at the 3 Position: Synthesis, Optical Properties and RI‐CC2 Calculations

et al. 2017

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The spectroscopic and the photophysical properties of isomeric environment-sensitive BODIPYd erivatives in different solvents are reported. The simultaneous presence of the stronge lectron-acceptorC F 3 and electron-donor NH 2 group in the structure of BODIPY,a sw ell as the positiono f the NH 2 group on the aryl ring, showedasignificante ffect on the spectroscopic and fluorescence characteristics of the BODIPY chromophore, both experimentally and theoretically. The comparison of meta and para derivatives (1a and 1b) shows that, in both cases, they have av ery low quantum yield (F f )a nd fluorescencel ifetime (t f )i nt he solvents used (except for n-hexane), therefore, they are potentially suitable as turn-onf luorescences ensors. The twisted intramolecular charge transfer (TICT) mechanism was adopted to explain solvate-induced fluorescence quenching. Besides this, there is as trong pH dependence on the photophysical behavior of the two isomers, which could also lead to applications as pH sensors. On the other hand, only 1a can be au seful probe for CO 2 sensing.O wing to aw eaker electron-donor character of the NHCOMe group in comparison with the NH 2 group, the position of the fluorescence "off-on" threshold of BODIPY 1c and 1d is shifted to the side of more polar solvents than for 1a and 1b.

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Section: Resultsmentioning

confidence: 99%

Environment‐Responsive 8‐CF₃‐BODIPY Dyes with Aniline Groups at the 3 Position: Synthesis, Optical Properties and RI‐CC2 Calculations

et al. 2017

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“…[16] Prior to the photophysical measurements the compounds were crystallized three times from cyclohexane/toluene. …”

Section: Experimental and Theoretical Methodsmentioning

confidence: 99%

Photophysics of cyanophenylpyrroles: Investigation of solvatochromic properties and charge transfer by ultrafast spectroscopy and DFT calculations

Basarić

Clementi

Carlotti

et al. 2015

Journal of Photochemistry and Photobiology A: Chemistry

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“…The spectral data matched that previously reported in the literature. 5 Melting point: 96-99 o C (dichloromethane) [lit. 103-106 o C]; 5 1 H NMR (500 MHz, CDCl3)  = 8.63 (br s, 1H, NH pyrrole), 7.27 (dd, J = 7.6, 1.6 Hz, 1H, H6), 7.14 (td, J = 7.7, 1.…”

Section: -(1h-pyrrol-2-yl)anilinementioning

confidence: 99%

“…5 Melting point: 96-99 o C (dichloromethane) [lit. 103-106 o C]; 5 1 H NMR (500 MHz, CDCl3)  = 8.63 (br s, 1H, NH pyrrole), 7.27 (dd, J = 7.6, 1.6 Hz, 1H, H6), 7.14 (td, J = 7.7, 1. 5 HRMS (ESI + ) calculated for C10H11N2 = 159.0917, mass found = 159.0921.…”

Section: -(1h-pyrrol-2-yl)anilinementioning

confidence: 99%

“…The spectral data matched that previously reported in the literature. 5 Melting point: 64-66 o C (diethyl ether/petrol 40-60) [lit. 78-79 o C]; 5 1 H NMR (400 MHz, CDCl3)  = 8.14 (dd, J = 8.1, 1.2 Hz, 1H, H9), 7.65 (td, J = 7.5, 1.3 Hz, 1H, H11), 7.53 (td, J = 7.8, 1.6 Hz, 1H, H10), 7.49 (dd, J = 7.6, 1.5 Hz, 1H, H12), 7.44 (dd, J = 3.3, 1.8 Hz, 1H, H4), 6.30 (t, J = 3.3 Hz, 1H, H5), 6.23 (dd, J = 3.2, 1.7 Hz, 1H, H6), 1.36 (s, 9H, H1);…”

Section: S5mentioning

confidence: 99%

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Cation-Directed Enantioselective N-Functionalization of Pyrroles

Armstrong

D’Ascenzio

Smith

2015

Synlett

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Supporting Information Reactions requiring moisture-sensitive reagents were carried out in oven dried glassware, under an atmosphere of nitrogen (balloon pressure). Dichloromethane, diethyl ether, toluene and methanol were purified by filtration through activated alumina columns employing the method of Grubbs et al. 1 Water was purified by an Elix ® UV-10 system. Reagents were used directly as supplied by major chemical suppliers, or following purification procedures described by Perrin and Armarego. 2 Petrol 40-60 refers to the fraction of petroleum ether which boils in the range 40-60 o C. Brine refers to a saturated aqueous solution of sodium chloride. Column chromatography was carried out using Merck Geduran ® Silicagel (40-63 m particle size). Analytical thin layer chromatography was carried out using pre-coated, aluminium backed plates (Merck Kieselgel 60 F254). Visualisation was achieved with ultraviolet irradiation (254 nm) and staining with vanillin. NMR spectroscopy was carried out using Bruker Avance spectrometers in the deuterated solvent stated, using the residual non-deuterated solvent signal as an internal reference. Chemical shifts are quoted in ppm, based on appearance rather than interpretation. Infrared spectra samples were prepared as a neat film and were recorded using a Bruker Tensor 27 FTIR spectrometer using an ATR module. Low resolution mass spectroscopy was carried out using ESI and was performed on a Micromass LCT Premier spectrometer. HRMS was carried out using Bruker MicroTOF and Micromass GCT spectrometers under ESI or FI conditions respectively. Analytical chiral HPLC was carried out using a Dionex Ultimate 3000 HPLC system comprising a Dionex LPG-3400A pump, WPS-3000SL autosampler and TCC-3000SD column compartment, and a Daicel Chiralpak column (0.46 cm x 25 cm), equipped with an appropriate guard column (0.4 cm x 1 cm). Melting points were determined using a Reichert melting point apparatus and are uncorrected. Optical rotations were recorded on a Perkin-Elmer 241 polarimeter. Concentrations are quoted in g/100 mL. S3 1.2 General Experimental Procedures General Procedure A: Imine Formation/Asymmetric Cyclization Imine Formation: A slurry of pyrroloaniline 1, the appropriate aldehyde and oven dried anhydrous magnesium sulfate in anhydrous toluene was stirred at room temperature for 16 hours and then filtered through a plug of Celite ® washing with anhydrous diethyl ether. The filtrate was concentrated under reduced pressure. Cyclization: The crude imine thus obtained was dissolved in toluene and N-benzylcinchoninium chloride was added. The resulting stirred suspension was cooled to the appropriate temperature and aqueous potassium hydroxide precooled to the appropriate temperature was added. The biphasic reaction mixture was rapidly stirred at the appropriate temperature for the appropriate time. After this time, water was added and the solution was allowed to warm to room temperature. The organic layer was separated and the aqueous layer was extracted three times with dichloromet...

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Optimization of the Suzuki coupling reaction in the synthesis of 2‐[(2‐substituted)phenyl]pyrrole derivatives

Cited by 16 publications

References 41 publications

Environment‐Responsive 8‐CF₃‐BODIPY Dyes with Aniline Groups at the 3 Position: Synthesis, Optical Properties and RI‐CC2 Calculations

Environment‐Responsive 8‐CF₃‐BODIPY Dyes with Aniline Groups at the 3 Position: Synthesis, Optical Properties and RI‐CC2 Calculations

Photophysics of cyanophenylpyrroles: Investigation of solvatochromic properties and charge transfer by ultrafast spectroscopy and DFT calculations

Cation-Directed Enantioselective N-Functionalization of Pyrroles

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Optimization of the Suzuki coupling reaction in the synthesis of 2‐[(2‐substituted)phenyl]pyrrole derivatives

Cited by 16 publications

References 41 publications

Environment‐Responsive 8‐CF3‐BODIPY Dyes with Aniline Groups at the 3 Position: Synthesis, Optical Properties and RI‐CC2 Calculations

Environment‐Responsive 8‐CF3‐BODIPY Dyes with Aniline Groups at the 3 Position: Synthesis, Optical Properties and RI‐CC2 Calculations

Photophysics of cyanophenylpyrroles: Investigation of solvatochromic properties and charge transfer by ultrafast spectroscopy and DFT calculations

Cation-Directed Enantioselective N-Functionalization of Pyrroles

Contact Info

Product

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Environment‐Responsive 8‐CF₃‐BODIPY Dyes with Aniline Groups at the 3 Position: Synthesis, Optical Properties and RI‐CC2 Calculations

Environment‐Responsive 8‐CF₃‐BODIPY Dyes with Aniline Groups at the 3 Position: Synthesis, Optical Properties and RI‐CC2 Calculations