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Synlett 2020; 31(06): 632-634
DOI: 10.1055/s-0039-1690828
DOI: 10.1055/s-0039-1690828
cluster
1,2,4-Triphenylpyrroles: Synthesis, Structure and Luminescence Properties
Thanks are due to the University of Aveiro, FCT/MEC for financial support to the QOPNA research Unit (FCT UID/QUI/00062/2019), CICECO–Aveiro Institute of Materials (FCT Ref. UID/CTM/50011/2019), financed by national funds through FCT/MEC, and also to the Portuguese NMR Network. This work was also supported by the Integrated Programme of SR&TD ‘pAGE – Protein Aggregation Across the Lifespan’ (reference CENTRO-01-0145-FEDER-000003), co-funded by the Centro 2020 program, Portugal 2020, and the European Union, through the European Regional Development Fund.Further Information
Publication History
Received: 07 January 2020
Accepted after revision: 31 January 2020
Publication Date:
13 February 2020 (online)
Abstract
Pyrroles are widely found in natural products and play an important role in biological processes. Certain pyrrole derivatives are fluorescent and may be used as molecular probes or biomarkers in the diagnosis of diseases, such as Alzheimer’s or Parkinson’s. Herein is reported the synthesis of five new pyrrole derivatives bearing phenyl rings on positions 1, 2, and 4, with electron-donating groups at the periphery. The introduction of more or stronger electron-donating groups red-shifts and increases the efficiency of the fluorescence emission.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690828.
- Supporting Information
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References and Notes
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- 26 1,2,4-Triphenylpyrroles 4a–e; General Procedure The appropriate nitro ketone 2a–c (1 equiv) was dissolved in a mixture of MeOH (8 mL) and THF (12 mL) then KOH (1 equiv) was added. The mixture was stirred for 2 h. The solution, cooled in ice, was added dropwise to an ice-cold solution of concd H2SO4 (4 mL ) in MeOH (10 mL), and the mixture was stirred for ~1 h at rt. Half of the solvent was removed under reduced pressure and the mixture was poured in ice–water. The product was extracted with CH2Cl2 and the organic layer was dried (Na2SO4) and concentrated to dryness to give compound 3a–c, which was used in the following step without purification. The appropriate amine (1 equiv) was added to a solution of the acetal 3a–c (1 equiv) in MeOH (5 mL), and the resulting solution was stirred for 24 h at rt. During this time a precipitate formed. H2O was then added, and the product was extracted with CH2Cl2. The organic phase was dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by flash column chromatography (silica gel).
- 27 1,2,4-Tris(4-methoxyphenyl)-1H-pyrrole (4c)Yellow–brown oil; yield: 23 mg (0.06 mmol, 11%). 1H NMR (300 MHz, CDCl3): δ = 7.50 (d, J = 8.8 Hz, 2 H), 7.15–7.08 (m, 4 H), 7.07 (d, J = 2.0 Hz, 1 H), 6.91 (d, J = 8.8 Hz, 2 H), 6.85 (d, J = 9.0 Hz, 2 H), 6.77 (d, J = 8.9 Hz, 2 H), 6.58 (d, J = 2.0 Hz, 1 H), 3.82 (s, 3 H), 3.81 (s, 3 H), 3.77 (s, 3 H). 13C NMR (75 MHz, CDCl3): δ = 158.4, 158.3, 158.0, 134.7, 133.8, 129.7, 128.3, 127.1, 126.3, 125.6, 124.9, 119.8, 114.3, 114.3, 113.7, 107.3, 55.6, 55.4, 55.3. ESI(+)–HRMS: m/z [M + H]+ calcd for C25H24NO3: 386.1751; found: 386.1743 (–1.99 ppm).
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